The clothes I buy on a whim always get the most play, and that got me wondering about other women’s wardrobe standbys. So I asked some stylish girlfriends about their basics.

Susan Wagner from The Working Closet

“My go-to item this summer has been the khaki City Mini from J. Crew.”

“It has an elastic “paperbag” waist that is perfect with a tank or tee and a skinny belt and a great A-line shape that makes my legs look thin (score!). I just bought the winter version, which is wool rather than cotton/linen, in bright dahlia, because it’s the perfect skirt and will go with everything I own and require no thought at all when I get dressed in the morning.”

Joanna Goddard from A Cup of Jo

“I’m obsessed with Emersonmade’s skinny jeans. They’re ridiculously flattering; honestly, they make me feel so sexy and shapely when I wear them.

“They’re super dark because they’re dyed with indigo. I wear them all the time, with T-shirts or blouses or sweaters.”

Katie Spence from Your New Favorite

“It is so very hot in Austin that mostly I wear skirts and dresses to keep things breezy. My favorite skirt this summer has been a chambray skirt that I got at Land’s End, but which is currently sold out.”

“However there is one on sale at Madewell that is almost identical. Lately I’ve been obsessed with natural fabrics, like cotton chambray and linen.”

Jordan Ferney of Oh Happy Day!

“These Gap slim crop pants in black. I can wear them with ballet flats or heels.”

“People dress up more here in Paris than in the US so these are my version of casual everyday pants.”

Rebecca Woolf from Girls’ Gone Child

Had to think about this because I don’t fit into any of my “usual” go tos (Ed note: Rebecca is currently 32 weeks pregnant with twins!), but last Fall it was this little corduroy half-jacket my friend Dani got for me at a thrift store:

(Ed note: If you want a crop jacket of your own, here are two to consider: 7 For Mankind Leather Crop, and a pattern for a simple cropped blazer.)

“My ‘go-to outfit’ is the dress + cardigan + booty + sock combo:”

Melissa Cotton from Poppy Cotton

“These are the most perfectly iconic ballet flats I have ever come across, and I have bought so many over the years looking for the perfect look and fit.”

“They are truly transformative to both my legs/feet and my outfit, quietly underscoring my entire fashion identity — classic and pulled together with a nod to the mid-century.”

Margaret Stewart from Fountly

“I have a dress I got this summer from Anthropologie that has proven to be the most versatile article of clothing I’ve ever owned. Seriously. I took it on a month long trip and wore it morning, noon, and (literally) night. Was great for sightseeing, casual or fancy meals, and (genius!) also an incredibly comfy nightgown.”

“Normally I shy from things without a waist; it’s my best feature! But in hot weather, it’s too binding to have a fitted anything! This thing was so damned comfy.”

Gabrielle Blair from Design Mom

“A scarf from J.Crew. It’s silk, but feels more like cotton, which I like.”

“It’s a warm pink and it has an almost florescent pink printed pattern. I picked it up on clearance last summer and I’ve worn it way too many days over the last year.”

(You can still find a couple of these babies on eBay, happy bidding.)

Interesting, right? Thanks, ladies!

Ok, team, now you. What’s your favorite item of clothing? If you have a link, all the better.

I went to Ousidelands with Mai from Fashioni.st, and she’s doing a whole series on festival fashion if you want to check out what people were wearing. (That’s one of her photos above.)

Mai and I were talking about how San Francisco weather requires a very particular style of dress for outdoor events. It’s colder here than people expect, and that’s true year round. Layering is key, especially for women. A few tips for balancing sanity with style:

Plan your outfit around sane shoes. You want flats with a closed toe. If you wear sandals your feet will get filthy, you won’t be able to dance in crowds without getting stomped, and in the evening it will get cold enough that you won’t be able to feel your toes. We’re not even going to discuss the idiocy of wearing heels in the dirt. Your smartest option? Boots.

Layer on top. The crowd shields you from wind, so you’ll be okay in something sleeveless if you’re dancing, but you’ll mostly need long sleeves — sweater, blazer, whatever. If you’re sensitive to cold (I’m looking at you Los Angles), you might want two thin layers on top of your tank.

Accessorize for warmth. You’ll want a hat or scarf after dark. Invest in a cotton, knit or silk scarf, something lightweight to maximize your bag-footprint to warmth ratio.

Keep it convenient. You’ll be using porta-potties all day. Reconsider leotards or body suits, especially in combination with tights. Tights in summer? That brings me to my next point.

Plan to keep your legs covered. Pants are a smart option no matter what time of year, but if you want to wear a skirt or shorts, throw a pair of tights in your bag, even if it’s the middle of summer. You’ll likely want them all day, but even if we have unusually warm weather, you’ll be pretty miserable without them after 4 p.m. or so.

Bring a little bag. It’s nice to be hands-free, but nicer to have a travel sized sunscreen, a place for cash and ID, sunglasses, and somewhere to store your scarf, sweater and tights when you don’t want to wear them.

See you next year.

This is my extraordinarily efficient friend Liz Stanley of Say Yes to Hoboken. In addition to being a total party animal, Liz is one of those people who can complete a cross stitch sampler, repaint the living room, and start a successful small business before she meets you for brunch.

She also has my favorite smile ever.

See?

Liz and I share a penchant for cruise director chic. Her khakis are American Eagle, and the gold striped tank is J.Crew from eBay. As you can see here, her house is just as well curated as her closet.

Liz’s pink ribbon necklace is also J.Crew and her blue blazer is from a thrift store. She says, “Shrunken blazers look hot with almost any outfit, but check the little boys section of your local thrift store for a cheap/vintage alternative to that $150 one you’ve been eying from J.Crew. I always find some great ones to add to my closet there.”

Her pink/gold heels were consignment, and they’re such a flattering neutral. The shine gives them a little more depth than a straightforward nude, and the pink is warmer too. Plus I love how a T-strap shoe always reduces blisters. I wonder if these were originally tango shoes.

Liz has baby-fine hair, so messy updos are a quick option for her. Everyday Princess Leia.

I told Liz I would crop the firewood out of the shot, but then the photo looked less awesome without it. Sorry, Liz. Now everyone will know you use your fireplace. Probably for something illicit.

Liz says, “Once you slip into a pair of high-waisted stretchy jeans like these, you’ll curse whoever came up with the idea of a low rise. There’s a reason our moms wore them in the ’70s, they’re incredibly comfortable. Plus, thanks to J. Lo’s butt, we can all embrace the full size of our behinds in high-waisted jeans.”

The scarf is from Target. If you always wonder how people make cool headbands from scarves, Liz recently posted a tutorial on her favorite turban ties. Go read it.

Her long-chain necklace is the Color Study Locket by Verabel on Etsy.

Bag by Fabric and Handle, excellent for toting your macrame project. Her sandals are Bernardo.

Here’s Liz with a pillow she probably whipped up in the ten minutes before she had a dozen guests over for dinner. Liz, I will pay you to be my wife. Tights by American Apparel, brown boots are Diesel from a consignment store, and the gray dress is H&M.

Liz and I were talking about what makes someone’s style stand out, and her theory is layering. She says, “With a kind of boring dress like this gray one I like to add unexpected pieces like an oxford shirt underneath and bright tights. I’m a big fan of oxfords as an under layer. Just be sure to roll up the sleeves and unbutton the top to prevent looking too stiff and formal.” Shirt is H&M, belt is from a thrift store

This sweet J Crew headband would get lost in my hair, but I love it paired with a chignon or a casual ponytail. Well played, Stanley.

Liz got this ombre silk skirt from a consignment store. She says, ““Elastic waist skirts aren’t always the most flattering on their own. Add a belt to cinch your waist and hide the extra bulk around the hip they’re giving you with a shrunken blazer.”

I’ve noticed over the years that a lot of Liz’s neutral-colored layering pieces feature an understated print like this tiny polka dot blouse from Urban Outfitters. It adds interest, but the overall effect is still classic. The blazer and brown belt are thrifted.

These boots are made for typin’ (by Zara).

Gah! I so covet this dress. She found it at a thrift store in Utah, and orignially it was sleeveless, backless, and nearly floor length, “I’m not a great sewer but I worked my fingers to the bone to refashion this outdated dress into something more my style.” You can see the whole process right here.

Here she’s styled the dress for day and evening.

Liz throws on a cardigan from Express, a the thin belt is H&M for a creative business look.

Also, there’s a removable back panel so Liz can still wear the dress to church.

For evening, she dresses up her shoes. Liz made these sequin shoe clips herself, but you can buy them readymade from Ban.do.

Here’s what the heels look like naked. (My Google search traffic on this post just skyrocketed.)

Add a vintage clutch, and you’re all set for some serious partying. That donkey tail isn’t gonna pin itself.

The denim skirt is thrifted and the striped top is Urban Outfitters. Anna Beth Chao only weighs like three pounds, so you can fold her right down into the exterior pocket of the carry-on. I take her everywhere. Chao and champagne.

The silk scarf is vintage Vera, and the aviators are from Anthropologie. When I wear them, I like to ask people for their license and registration at regular intervals.

There was a cocktail party that first night, so I wore my vintage fringe happy dress, which requires zero ironing. I take it everywhere.

These are my fallback shoes, which operate on the theory that if you’re a woman over six feet tall in heels, no one notices what you’re wearing anyway. I need a new pair, because I’ve had these for nearly a decade. It’s impossible to find stable, comfortable, unreasonably tall shoes, but it’s time. Help a sister out, Internet.

The next day was my presentation. I like to be totally comfortable on stage, so I went with this simple navy shift from H&M and swapped the belt out for a striped scarf. The orange travel flats are Tieks, and I also wore two square glass orange rings, because I like to be matchy matchy like that. You’ll see those below.

A group of us went to dinner later that night, and I wore a romper I got at Forever 21 for 16 cents. Cheap prices for disposable clothing is why I continue to shop there, even though they purposefully play music to annoy people my age. You’ll have to more than blast Avril Levigne to drive me away from prices like this Forever 21! Actually, I love that “What the Hell” song, so I’m golden. I am bopping in the aisles, Forever21.

I wore the romper with very basic open toe black flats from H&M. I don’t have any full-length shots of this outfit that you haven’t already seen, so I’m cheating by using a shot from New York. There are, however, several shots of me looking naked at dinner:

“Oh, don’t mind me. I put a dinner napkin on the chair before I sat down.”

This is my impression of cruise director Julie McCoy. Can you feel me setting a course for adventure?

The skirt is from Buenos Aires, and the tennies are knockoff Bensimons, which I got on the cheap at the now-defunct Martin and Osa. I need to replace those badly, but can’t bring myself to spend $50 on a pair of slightly more awesome canvas Keds.

Scarf is another vintage Vera tied as an ascot. The button-up shirt is from The Limited, which makes great shirts for business travel because they aren’t 100 percent cotton, which means they have stretch to them and don’t wrinkle nearly so easily. My glasses are Dolce and Gabanna.

That night I wore an American Apparel dress for my reading, with the same heels we talked about earlier.

As you know, I like to take jammies that I can wear as clothes in a pinch. This time, I packed this grey romper, also from Forever21, also 16 cents. The cashmere sweater is from the Alameda Flea Market.

I stayed a couple extra days with Anna Beth, so I revisited the navy shift for lunch at Commanders Palace. Here you can see the aforementioned orange rings, which I got from street vendors in Buenos Aires:

I also wore my stripe top again, this time with a little black mini from Urban Outfitters:

And a scarf from H&M:

Again, I failed to get a photo of what I wore on the plane due to exhaustion. I know this makes you rabid, so I’ll say I wore a short cotton mini-dress over tight jeans with the gray striped sweater, a blazer, and the white sneakers.

And that’s it, team.

One day soon I’ll do a post about what I wear on planes to maximize comfort and go from cold (San Francisco) to warm (everywhere else). Speaking of which, do you have a standard travel outfit? If so, spill. I could use a variation on the dress/leggings/sweater theme.

Also, keep an eye on this space, because I asked Roxanna from Everyday Treats to tell me what she packed for New Orleans. She always looks amazing, and she sent photos. Hooray, Roxanna!

In an effort to gather all my writing in one place, every Monday I post articles that originally appeared elsewhere, or work that has been gathering dust on my hard drive. This piece was originally published by the The Morning News in 2002. Thanks to Rosecrans Baldwin, for the edits.

If you look like you just got some, it’s sexy. If you’re dressed like you’re out to get some, it’s slutty. In the fifth part of this women’s fashion series, I encourage you to ignore the distinction.

Sit down, my love, I’ve a bitter truth to tell. All of us are gravity’s bitches. Barring superhuman — and perhaps surgical — efforts on your part, your body is never going to look better than it does at this moment. Fortunately, your body already looks pretty damn good.

Don’t believe me? Gain some perspective. Look back at your high-school photos. You would kill to have that ass again. Perhaps this makes you feel glum about your current ass. Well, stop it. When you’re seventy you’ll look back at today’s photos and realize how much time you’ve wasted fretting over a perfectly sexy bum.

If you don’t wear daring clothes because you worry about your cattier girlfriends snickering, I suggest you lose those particular girlfriends and replace them with a buttery pair of understanding leather pants.

Suck in your gut, yank on the pants, and call your raucous girlfriends, the ones who will whistle and holler at the new rock-star you when they pick you up for a night on the town.

Congratulations, sexy thing. You’ve discovered the first of five rules for dressing slutty without feeling slutty:

1. Be Confident
What about modesty? Humility? Saving it for the guy at home? Screw that. There’s nothing wrong with feeling pretty, sexy, fabulous. It’s especially affirming to feel that way in front of a large audience, Tina-Turner style.

Perhaps you aren’t a naturally confident kind of gal. That puts you with about 95 percent of the population. Fortunately, being confident and pretending to be confident are essentially the same thing.

Most women who look ‘willing’ in their slutwear seem that way because they’re seeking approval. If you’ve ever worried that you’re dressed like a hussy, you’ve probably never even come close.

Girls who dress inappropriately do so with intent and grave insecurity. They tug at their tops, constantly hike their low-riders, and pretend not to notice that their pants have camel-toed in their crotches. You’re not one of them. The rest of our rules will help you avoid inadvertently looking like one of them.

2. Be Prepared
The peril in wearing revealing clothing is that it sometimes lives up to its name. Worrying that your left nipple is playing peek-a-boo with your date will destroy your crucial self-confidence. As we’ve discussed, worry makes you look trampy instead of vampy.

If you’re wearing a winningly low-cut tank or a blouse with a loose neckline, invest in some double-sided fashion tape to keep the garment in place. Short skirts call for boy-cut underwear in a matching shade so viewers either aren’t sure of what they’re seeing or realize there’s not so much to see. The lowest low riders need a tight belt to ensure that the waistband never affords a view of your continental divide.

In every case, the proper undergarments—stick-on bras, nude G-strings, the occasional girdle—will bolster your self-esteem. It can look like your blouse is always on the verge of falling open, as long as you know it isn’t. Illusion is our friend.

Often what makes a sexy outfit look skanky is a lack of attention to detail. When you’re getting ready to wear something trashy, groom what’s showing. You want to look artfully mussed; you don’t want to look like a heroin-addict on the prowl. Make sure you smell nice and clean, that your nails are neat, that you’ve paid some attention to your hair, and maybe dab on a little lip gloss if you don’t normally wear makeup. In the winter, self-tanner is almost never a bad idea (as a pasty Irish girl, may I recommend the Bain de Soleil line of offerings), and a little of the Body Shop’s Body Butter on your legs will give them a Sports Illustrated Swimsuit Edition gleam.

3. Be Comfortable
You can’t be breezy if you’re limping. You know you’re going to be walking from bar to bar and dancing the night away, so don’t toddle along in ten-minute shoes. It will annoy everyone who has to wait for you to catch up. Save the spike heels for sedentary tête-à-têtes. Little kitten-heels, open-toed shoes, and sling-backs all have slut-appeal, and they’re much kinder on your delicate arches.

If you want to wear something tight, don’t just buy it a size too small. It will cut into your armpits and bunch unattractively in odd places. Buy clothes that fit. That means an item may cling to you, but you’ll still be able to sit down and breathe normally, and you won’t be continually coaxing it into place.

4. Remember Your Body Type
Accentuate the positive, darling. Maybe your bum could crush a large village, but your boobs are porn-star fabulous. Perhaps your butt drops off like a cliff, but your legs take their time getting to the floor. There are clothes out there for you — sultry clothes — and you should be wearing them more often.

Hide what you want to, reveal the choice pickings. Every girl’s got something admirable about her shape. If you’re not sure what your best points are, enlist a few brutally frank friends.

Your body type will determine what you can get away with. If you’re 5′11″, an eeny-weeny skirt is going to raise some eyebrows. If you’re 4′11″, it’s kicky. Hip-huggers can be tempting or tomboyish, depending on the view from behind. And if you’re a D-cup, you’ll look much racier in a plunging neckline than your AA friend.

Keep these things in mind when you’re choosing what you’ll wear with a sexy piece. If you’re showing a lot of cleavage, then that will help you decide what to wear on the bottom, which brings us to our next point.

5. Find a Balance
If you’re not quite ready to bare it all (or any portion thereof), the easiest and most effective way to wear arresting clothing is to pair it with something mild. If you buy a leather miniskirt that precludes sitting down, wear it with a turtleneck sweater and some tall boots. If your dress is so low-cut that you have to tape the neckline in place, the skirt can be loose around your bum and fall below your knees.

This rule also goes for your toilette. If you’re wearing a transparent T-shirt over a bra-top and you’re not sure if you can own the look, choose dewy, natural makeup instead of the dried-blood lipstick. You can also class things up by going for a more conservative hairstyle. A clingy dress with a tidy chignon can look classy and daring, while the same dress with teased-up hair-band bangs is questionable.

If you’re too modest to show much skin, choose pieces that are sexy without being revealing. Leather pants in a trouser-cut, suede tops, knee-high boots. Or you can opt to reveal less traditionally erogenous zones by wearing low-cut backs, necklines that expose your collarbone, or shirts that have cutouts in unexpected places.

If you’re really timid, test the waters with touchable fabrics like cashmere and angora, or decorative cloth that simply catches the eye with beading, sequins, or texture.

The more you wear something, the more comfortable you’ll be. So break in your new painted-on jeans by strutting around the apartment for a few days before you venture out in public.

Ready, Set, Slut
It’s difficult to seem fun and impossible to seem dangerous in a pair of Gap khakis. No one ever felt like purring in a polo shirt.

You’re not some milquetoast, wallflower, soccer-mom wannabe, you’re a kitty-cat, you’re a doll, you’re Marilyn Monroe. Dressing sexier will not only change people’s perceptions of you, it will alter your idea of yourself.

Tug on those leather pants, and turn up some Aretha. You’ll see what I mean.

In addition to being a dear, she is a powerhouse. Her site, Design for Mankind, was featured in the London Times as one of the top 50 design blogs in the world, and right now she and her husband are renovating their cabin and documenting the process for HGTV.com. She does not sleep.

I love Erin’s sense of humor when it comes to fashion, so I told her we needed to do a Mighty Closet next time she was in town. She offered to take some photos herself and pass them along instead. Genius. So here she is, Pocket Loechner, coming to you live from Fort Wayne, Indiana. Take it away, my sweet.

(Photos by Casie Towsley.)

Outfit One: Running Errands

This is an example of what I’d wear out and about, either to the grocery store, post office, or a coffee run. I used to reserve these types of activities for yoga pants and a hoodie, but I recently pixied myself and you’re not allowed to wear pixies and sweatpants. Unless, of course, you don’t mind being called ‘Sir’ in the cereal aisle. Hypothetically.

Pinstriped Oxford Shirt (Men’s): Banana Republic, Circa 2001
Navy Grandpa Cardigan: Heritage1981 I love the leather elbow patches!
Boyfriend Jeans: Levi, Circa 2004 The trick with wearing boyfriend jeans is to really buy men’s jeans. I’m totally not kidding here.
Boots: Antique, they were my grandmother’s!
Handbag: Vintage, thrifted
Frog Cocktail Ring: Vintage, thrifted

Outfit Two: Birthday Party

Maggie asked for a cocktail party look, but we don’t have cocktail parties in these parts. So this is an outfit I’d wear if I were throwing myself a party.

Dress: Forever 21
Tights: WeLoveColors.com
Heels: ModCloth
Silver Sputnik Cocktail Ring: Antique, thrifted
Hairpiece: Tieks shoes come with this little ribbon around the box. I got a pair at the Mighty Summit, and thought the ribbon would make a cute headband.

Outfit Three: Working At A Local Cafe

Striped Sweater: F21
Confetti Skirt: Modcloth
Purple Tights: WeLoveColors.com
Navy Patent Wedges: Vera Wang, 2008
Gold Necklace: LemonadeHandmade This was a gift from the Mighty Summit.
Cocktail Ring: Vintage, Alameda Flea Market

Outfit Four: Lunch With Grandma

I don’t have any friends in Fort Wayne yet, so my most frequent lunch companion is my husband’s 90-something-year-old grandmother, who is fantastic and a total treat to hang with. Seriously. Anyway, this is what I’d wear to lunch with her, because she loves quirky boots and mixed patterns, and I enjoy surprising her with my latest combos. (Don’t tell anyone, but she just might be in direct relation with Iris Apfel. Never can tell!)

Striped Navy Boatneck: Land’s End Canvas
Striped Cardigan: F21
Herringbone Skirt: Tucker for Target Collection
Tights: Urban Outfitters, 2005ish
Boots: Anthropologie, Fall 2007
Brooch: Brooklyn Rehab, Gift
Cocktail Ring: Vintage, thrifted

Outfit Five: Out On The Town

This is an outfit I’d wear for an evening dinner with my sweet, sweet husband. You’re allowed to wear fake fur wherever you want in Indiana, so I take full advantage.

Dress: Tucker for Target (sold out online, but check your local store)
Faux Fur Vest: Vintage, thrifted
Belt: ModCloth
Shoes: ModCloth
Tights: ModCloth.com
Cocktail Ring: Vintage, thrifted
Cicada Earrings: Erica Weiner Jewelry

Notes:
1. I always wear a cocktail ring on my right index finger. It’s a staple of mine, and you’ll rarely see me without one.
2. I invest in jewelry, shoes, and little else. If an item has a pattern of any kind, I never pay full price, as patterns (with the exception of Breton stripes) are much easier to date than solids.
3. Colored tights are another staple, and I store these next to my cocktail rings. Snags ensue, but I consider colored tights and cocktail rings to be the President and Vice President of my wardrobe, so they can’t very well sit amongst the minions, can they?

—————

Oh, Erin. How many times am I going to have to ask you to send me your grandmother’s boots before you bend to my will? Thanks for all your hard work putting this together. If I can’t have you in my pocket, having you in Mighty Closet is the next best thing.

In an effort to gather all my writing in one place, I’ve been posting articles that originally appeared elsewhere. This piece was originally published by the The Morning News in 2003. Thanks to Rosecrans Baldwin, for the edits.

A girlfriend of mine just went through a particularly hard year — divorce, career upheaval, the possibility of leaving her beloved bungalow. We were talking about New Year’s resolutions, and she said she was going easy on herself. Her only resolution was to accessorize better. Screw the gym — this is a goal I can get behind.

Designers draw from the past, and so should you. The oft-repeated rule is that styles are recycled every twenty years or so. Wearing something that was once all the rage but has since fallen out of style will make you seem fashionable without risking disasters.

This is my list of standbys from decades past. I skipped the ‘90s because I still don’t have enough emotional distance to recommend that you bust out your shrugs. Forgive me.

1910s
Full-Size Umbrellas
Why do we wear shoes that make our feet bleed, but refuse to carry an umbrella that won’t tuck into our purse? Half the convenience, ten times the appeal, the full-size umbrella with a wooden hook handle is too charming to abandon. How forlorn to browse in a bookstore, sip a latte, or buy a paper on a rainy afternoon without one.

1920s
Fans
Aren’t fans sweet? They’re light, compact, and they drop right into your purse. If you live somewhere hot, or you like to go out dancing, it’s such a comfort to have a portable cooling system with you, and so much more attractive than fanning your sweaty neck with a magazine. If you live in a big city, head to the nearest Chinatown and pick one up for a buck or two. I’m a sucker for cherry blossoms.

1930s
Gloves
Without a decent pair of gloves, what do you suppose you’ll use to slap your offenders? Maybe white cotton gloves are a little too precious (and OCD indicative) for afternoon shopping trips nowadays, but dress gloves are so suave with an evening gown. I’m also in favor of colorful, soft, leather gloves for the winter. Try deep green with your black coat or a soft blue to offset chocolate. Leather gloves give such a satisfying thwack when defending one’s honor.

1940s
Back-Seam Stockings
You can wear them slutty, classy, or somewhere in between. Where else can you get that kind of versatility for ten bucks? Back-seam stockings lend ba-boom to the most mundane dress or shapeless skirt. Black is a classic choice. Please straighten your seam, or you’ll look as though you’ve just had a tryst in the broom closet.

1950s
Vices
Cigarette smoking is a nasty habit. Don’t cigarette cases make it ever so much more attractive? Press the precise, silver button, and pop! A tidy row of cigarette soldiers waits to defend you against the evening chill. Offer one to a friend; give him a light with your shiny flip-top lighter. (Plink! Tiny flame. Plink! Pocket-ready.) And for god’s sake, get yourself a drink. Why do you think they call it a cocktail dress?

Brooches
Brooches are nostalgic, and rarely the first choice when you’re digging through your jewelry box. They’re just grandma enough to qualify as quirky, and a very simple outfit is elevated with the right pin.

1960s
False Eyelashes
A kittenish sidelong glance is nothing without them. Buy a pack of individual lashes and some lash glue at the drugstore. Put a couple of lashes on the outside corner of each eye, and maybe one in the middle to even things out. Paint on some black liquid liner and give yourself a slow wink in the mirror. If you don’t want to have sex with your own reflection, you’re doing it wrong.

1970s
Pom-Pom Hats
The more interest you take in your wardrobe, the more you’ll realize that caring too much about what people think can be the kiss of death. When everyone is wearing their sleek little black watchmen’s caps, nothing says ‘piss off’ like a ‘70s-style pom-pom ski cap in Lifesaver colors. Orange and green stripes, or navy blue and white topped with a cherry-red pom—this is clothing that bobs when you walk! Right on.

Crocheted Beer Can Hats
Perhaps you’ve seen one of these at a thrift store. You cut beer cans into squares or ovals and then crochet them into a hat. Eh? Eh? I’m kidding. Take it off.

1980s
Bows
You had to give up your side ponytail, but don’t let go of the bow. Try it at your waistline, on your shoes, or tie a long scarf into a headband with a bow at the top.

The Details
Every time you leave the house, consider wearing, or carrying, one unique thing that makes you a happy kid. If you have an unusual accessory, you can throw on a black turtleneck and a ho-hum pair of jeans and still seem hip. The unexpected diverts attention from the mundane, and stocking up on wacky vintage brooches is a lot cheaper than buying an electric-green Cashmere coat. Also, electric green isn’t your color.

This hat, right here, is how I feel about Fall.

I changed into one of those horrifying velour tracksuits that was very popular at the time, and one of our groomsmen remarked that I looked like a movie star trying to go incognito. Mostly I just wanted a zip-front something to wear all day so I could change out of it without ruining my hair and makeup. Also I might have wanted to practice a cheerleading routine or something. You never know.

(That kissable bundle is little Evan Frasier; I was his nanny briefly. He is 43 now.)

My dream wedding dress was Audrey Hepburn’s bridal dress from Funny Face:

I’ve mentioned before that I have clothing nightmares. We were on a tight budget when we were married, and I was accordingly horrified by the idea of spending $1,500 on a dress.

I was set on a short dress, which I thought would be easy to find, but absolutely no one wore them at the time. When I say no one, I mean I went to every bridal salon and department store in San Francisco, and found exactly one short, white dress, for $1700 dollars. It was not cute.

Three months before the wedding I still didn’t have a dress, and I was beginning to hyperventilate and have tooth-griding nightmares. For those of you who’ve never been married, lots of women order their dresses a year out, and many bridal salons look at you like you’re nuts if you expect less than a six-month turnaround.

Bryan finally had enough of my whimpering and rocking in the corner. He said, “We are going to the Gunne Sax outlet and buying something.” We ended up buying two dresses, one that would become the bodice for $80, and a size 14 tulle monstrosity for the skirt, which was about $100. I asked my dear friend Lisa (Hi, Lisa!) from Stitch Bitch if she could lop off the skirt and smush the two dresses together. She did it for less than $100, because she loves me. This is how we ended up spending less for my dress than we did for the bourbon at the wedding. Fact!

Lisa didn’t want the dress to be too heavy, so instead of using 300 layers of tulle, she put some horsehair ruffs under the sides of the skirt to make them stand out. This meant that the skirt was nice and poofy, but I could still use the restroom withoutout aid. Bonus.

I got a satin headband at Britex, and my mom-in-law sewed a circle of tulle to a metal hair comb the night before the wedding. I’d hoped for a cage veil, but this was in the hours before Etsy, and they were impossible to find. I thought about skipping the veil entirely, but when my girlfriends pinned my veil in my hair, it was the moment I realized I was really getting married.

I grew up with a gardenia bush in the backyard, so I had a gardenia in my hair and one for each of the bridesmaids. They wore them in their hair or pinned to their shirts as they chose.

Thanks to tequila and vigorous dancing, my hair flower fell out, and no one mentioned it because they didn’t know I had 14 more in the back. Word to the wise brides, extra hair flowers ladies.

I also wore red shoes, which was strange at the time. One of our guests mentioned that he particularly loved my shoes because his mother always said red shoes were for little girls and whores. I like to think I fall squarely in the latter camp:

Later, I pulled on a red sweater with a rhinestone brooch, because it gets cold on the docks in San Francisco. The sweater was a merino Bennton cardigan, and I still wear it.

Bryan’s suit was a striped Donna Karan cashmere blend on sale at Nordstrom Rack. His tie was Calvin Klien. My maiden name is Berry, so the boutonnieres were Eucalyptus leaves with unripe blackberries, all collected on the wedding site. We asked our groomsmen to wear black suits, and we got them matching ties.

My bridesmaids were from size 0 to size 14 and were 4′11″ to 5′10″ — we even had a pregnant attendant — so I had to find something that would be flattering for everyone. I chose white cotton wrap tops and red wool skirts from Foley’s, which I asked the bridesmaids to wear full length or have hemmed to the knee as they chose. My bridesmaids actually did wear the pieces again, and the whole outfit was $70. Separates!

Pro tip: When you’re getting married, it’s helpful to have girlfriends who are all knockouts. I love you, girls.

Old? A penny in my shoe. New? My dress. Borrowed? My lipstick. Blue? My engagement ring, which is a giant ’60s era cocktail Aquamarine. Oddly, I do not have a close up photo, but it is lovely.

For the rehearsal dinner I wore a red, heavily embroidered shift, of which I also cannot find a single photo. By the end of our wedding I was so through with red that I could barely look at a tube of lipstick without shuddering, but seven years later I’m coming back around.

In an effort to gather all my writing in one place, I’ve begun to post articles that originally appeared elsewhere, or work that has been gathering dust on my hard drive. This piece was originally published by the The Morning News in 2002. Thanks to Rosecrans Baldwin, for the edits.

Flappers never had bad-hair days. They lopped off their tresses, tugged on a cloche, and headed out for an evening of Charleston and bootleg gin. What’s more, flappers wore comfy dresses shaped like potato sacks. They could wear whatever they liked; who the hell notices when you have that darling bell of a hat on? And so, you see, hats make life easier and loads more fun.

Unfortunately, hats have gotten a bad rap since they fell out of quotidian fashion in the late 1960s. Have you ever flirted from beneath the brim of a fedora, shaded your unblemished complexion from the summer sun with a straw hat, or sipped cappuccino thoughtfully in your beret? Of course not. All but a very few of us have abandoned hats to the crazy ladies.

Did I say crazy? Pardon me, I meant ‘eccentric.’ By eccentric I mean, ‘enamored of hot-glue guns and their ability to affix small, fake birds to felt.’ These are not the kinds of hats in which we’re interested. That is, unless you’re dressing as a Hitchcock movie for Halloween.

* * *

Milliners will tell you that anyone can wear hats. They are lying.

Some women do not look well in hats, just as some should avoid turtlenecks or string bikinis. That said, many women believe they look terrible in hats, but in reality simply don’t know how to wear them. There are five ways you can dramatically increase your odds:

1. Find a color that complements your skin. Hats are closer to your face than anything else you wear. Hence, if the color isn’t flattering, it will be especially noticeable. I know it’s the sweetest hat you’ve ever seen, and it would look so great with your boots, and it matches your eyes, and so on. Try the hat in a natural light. If it makes you look sallow, put it back.

2. Wear your hair differently. Many women just plunk a hat on top of their everyday hairstyle. If you already have a wide face, this can exaggerate it to an unflattering effect, especially if you have long or full hair. If you really like a particular hat, but just don’t think it works on you, try pulling your hair back in a tight chignon or a low ponytail at the nape of your neck, or pinning the front sections back. At the very least, tuck hair behind your ears. It may improve matters dramatically.

3. Choose a hat that works with your face shape. If you have an oval or triangular face, you’re one lucky bird. You can wear almost any hat, and you can wear it as far forward or back as you please. You can also pick any kind of brim without looking like you’re wearing a life preserver on your head. The hat’s crown (the part that fits down over your head) shouldn’t be narrower than your cheekbones.

If you have a round or square face, wear your brims on an angle when possible. You’ll want the crown of the hat to be at least as wide as your face. Hats with a wide, high crown will work especially well.

If you have an oblong face, stay away from tall hats. Wide brims will counterbalance the vertical stretch. You might also try pulling the brim down to your eyebrows to shorten your face and to hide excess forehead.

4. Make sure the hat is angled to its best advantage. If a hat doesn’t look good when you first try it on, you may not be wearing it far enough forward or back. Many hats, especially stiffer hats made of felt or straw, will also wear better when you tilt them slightly. Try angling your hat to the right or left, and look at it from every direction in the mirror. It may look good from the front, but terrible from the side. Keep fussing until you find a position that works. If you can’t, assume that the hat is ugly and keep shopping.

5. Be sure you’re wearing the correct size. The average female head size is twenty-two and one half inches. If the hat comes down over your ears, or falls off easily, you’ll want a smaller size. If you fuss with your hat, or if it makes your forehead itch, go up a size or two.

Hat Quality
If you’re headed to Ascot this year, you’ll want something nice. A quality hat is relatively easy to distinguish.

Straw-hat making is a time-consuming endeavor, as they are almost entirely hand woven. Most of them are produced in China and the Philippines. Straw is braided, and then sewn into shape. The most prized straw hats are produced with a fine straw, in a small, tight weave. A hat of good-quality straw can take a weaver up to twenty-five hours to complete.

If you’re buying a felt hat, look for wool felt, peachbloom, or fur felt, which is made from rabbit fur. More expensive felt hats are often lined. Hat trim should be sewn on to the hat’s form, and not glued in place.

Many of the hats you see on the street are ‘factory hats.’ Mass-produced, and made of lower quality materials, these hats are practical and mostly casual. Designer hats are a step up. They often have limited production runs and are made of high-quality materials.

The haute couture of the hat world is called ‘model millinery.’ These extravagant hats are hand-sewn and pieced together using only the finest materials. They’re often made for a single customer who is attending a particular event, after which the design is retired.

Storage and Repair
Store more expensive hats in hat boxes to keep them from getting dusty or discoloring in the light. Line the box with tissue paper and place crumpled paper in the hat’s crown to help it hold its shape. You may want to overstuff the crown a bit so the brim of the hat lifts up from the bottom of the box. This way the paper supports the hat’s weight, and the brim doesn’t become distorted. Add enough paper to your box so that the hat will not move if the box is jostled.

Don’t wear hats in the rain, unless they are rain hats. Nothing damages a hat more quickly than water, except perhaps fire. Don’t wear hats in the event of a fire.

If you have a felt or straw hat that’s been dented, you may be able to repair it with steam. Put a full kettle on to boil and wait until it begins to steam consistently. Turn the heat down a bit, but be sure the steam still has a little force to it.

Place the dent over your steaming kettle and move your hat around until the steam penetrates evenly. (This should take about twenty to thirty seconds.) Remove the hat from the steam and use your fingers to push the dent out, and then blow on the affected area to cool it. Use caution when you’re working with steam in a small area: too much can exacerbate damage.

You can also make an old hat stiffer by steaming it thoroughly and letting it cool. This reactivates the stiffening agents milliners used to make the hat.

If all of this sounds too complex, or too burn inducing, most milliners will reblock your hat for a fee.

Hat Types
Hats are either brimmed or brimless and they take two forms—a hat or a cap. Milliners fancy up the basics with trims and detailing. A few types of hats and their preferred uses:

Alpine: Down-filled fabric hat with storm flaps for ears, neck, and forehead. Perfect for hunting wabbits or hiding winter hickeys.

Beret: Felt cap with wide circular crown. For coffee, commutes, scouting, miming, and youthful affairs with political leaders.

Chignon Cap: A piece of fabric that covers a bun. Ideal for naughty-French-maid Tuesdays.

Cloche: A ‘20s felt hat that resembles a bell. Useful for blocking unwelcome eye contact when you’re trying to read on the bus.

Cowboy Hat: Originally developed for cattle herders, it has evolved into a signal that you are attending a bachelorette party.

Derby (or Bowler): Domed crown with narrow brim that curls upward. Excellent for Charlie-Chaplin costumes.

Fedora: A men’s hat that has since been adapted for women’s wear. Brimmed, and made of felt with a lengthwise crease in the crown. Effective for modern-jazz-dance routines when worn with a men’s-style shirt unbuttoned indecently.

Newsboy Cap: Full fabric cap with visor. Great when paired with knickers for ironic rounds of golf at your local putt-putt course.

Stocking Cap: Knitted, with a long tail that often ends in a pompom. Good for midnight runs through town with a candle, or snowboarding in 1995.

Watch Cap: Knitted sailor cap that rolls down or up depending upon your warmth needs. Best stolen from a boyfriend just before you tell him you know about that girl.

Hats Off
Though a gentleman must remove his hat indoors, ladies can wear theirs wherever they like. However, don’t wear one in your own home when you’re hosting a party. Otherwise, it looks as though you’re about to head out someplace better.

Hats draw attention, so it takes confidence to wear one well. If you can manage it, other women will assume that you are more fashionable than they. Those women will be correct.