Courtney is a champion thrifter and, shoes aside, this outfit is all second hand. The nautical-stripe dress has a ’50s vibe, but it’s actually a Vicky Vaughn piece from the ’80s. Perfect for standing purposefully on the bow of a ship, fisted hands on hips, grinning at the horizon.

Also, how enviable is her office nook? So tidy!

Courtney found the belt on the sidewalk in the Western Addition. I know that mighty sound alarming to some of you, but be ye not scandalized. People in the city just leave bags of belongings on the curb instead of lugging them to thrift shops, and decent stuff rarely sits outside for more than an hour or two.

The painted chain is from a white elephant sale. The moony eyes are from her mama, who did some catalog modeling in her day. Thanks for the good genes, mom.

These are Courtney’s go-to eyelet flats, which she realized she wanted to replace just as I was aiming my camera. San Francisco is a walking city, so flats get heavily abused. Comfy flats are by Rocket Dog, and she got them on Zappos.

Tomorrow, Courtney’s favorite jacket, which she purchased in Spain. Olé!

This is my dear friend Libby Nicholoau. If she looks familiar, you probably recognize her from our trips to Argentina and Mexico. Libby is the Gallery Director for the Shooting Gallery in downtown San Francisco, which features a lot of Low-Brow, Urban art, so her closet reflects the gallery’s independent spirit.

Libby is the girlfriend I consult when I need to know whether my beloved jeans have become mom jeans, or whether you can guess which year I graduated from high school just by looking at my dated shoes. I have to press her for an opinion, because her Southern manners prevent her from volunteering the information, but she’s never steered me wrong.

Right now, Libby’s working hard to establish herself, so she prefers to spend her money on travel and bar tabs. She buys most of her clothes second hand, and trades key items with roomies and friends to help keep her outfits looking novel.

These are four outfits she loves, plus her favorite cocktail look:

Believe it or not, this is office wear for Libby. Most of her clothes are day-to-evening, so she can leave the gallery and head straight to art openings or drinks with friends. Skirt by Paris L.A., purchased at Buffalo Exchange.

Shirt is Xhileration by Target, purchased at Goodwill.

Libby got this chain at a thrift store, the pendant was a gift from mom, and the vintage key was a party favor from our Mighty Haus shindig last year.

Libby bought her Steve Madden shoes at a Shoe Pavilion liquidation sale, “There was a line out the door, and when I figured out what was going on, I was like YES!” She loves these American Apparel tights, which she often borrows from a friend. “Jillian and I trade. We have openings every month, and art fairs three times a year. It’s fun to put together a new outfit for everything; everyone’s so creative about what they wear. I feel like I work on stage sometimes. You’ve gotta have costume changes!”

Here’s Libby just before she heads off to meet friends at a cafe in Paris. We should have posed her on a bike with a baguette sticking out of the basket.

The scarf has more pattern to it than you can see in the photos — she’s good about combining patterns in non-fugly ways. Her skirt is by Paper Doll L.A. and was purchased at Buffalo Exchange, where she got this whole outfit, except for the shoes (Goodwill), and the vintage scarf, which I gave her.

Incidentally, the scarf is by Colette.

Soft ruffle tank top is Aviva. Nice to have a basic piece with that little unexpected touch of femininity.

Perfect sling-back peep toes by Nicole. Vintage straw bag.

This is Libby’s favorite outfit. She says, “I love a tunic with leggings. I feel so confident and comfy. Plus, I can wear it anywhere without worrying too much about the scene.” Headband by H&M.

Vest is H&M, as is the necklace. Top is Forever 21, purchased at Buffalo Exchange.

The stud-inspired bracelet was on loan from Libby’s roomie, Jessica.

These ankle buttons on the leggings are killer, and I like them pulled down over the backs of her shoes. Libby got the leggings second hand at Crossroads, but they’re made by Effie’s Heart.

Suede wedges by Chinese Laundry, purchased at Goodwill.

I actually bought this H&M tent dress when I was pregnant, and almost never wore it. Libby had borrowed it once, and I felt silly in it, so I asked if she wanted it. Needless to say, she rocks it completely differently than I did. She wore this outfit recently to a California Academy of Sciences Nightlife event, and apparently it was a hit with the boys. Smart guys love Libby.

The belt was a gift from her mom.

The feather earrings are from Buffalo Exchange.

The hair was my doing. I think I got the idea for a bobby-pin headband from a scene in Amelie.

Shoes are B.C., purchased at Goodwill.

I so wish I’d gotten a better picture of these much-loved tights. So great.

Space cowgirl! This is another work-to-evening outfit for Libby. The tunic is H&M via Goodwill, leggings are American Apparel.

The belt is from a thrift store in Virginia, Libby’s home state.

I think I want some feather earrings. This shoulder duster is also on loan from Libby’s roomie, who got it somewhere in the Mission. Good on the dance floor, bad in a cat fight.

She has no idea where she got the ring.

Boots are Corsina, purchased at Buffalo Exchange.

Here’s Libby’s little black dress. It’s from H&M, as is the chunky bracelet.

It has little pleats on the upper back. Aww.

She got her galleon necklace at a tradeshow at 111 Minna, but sadly couldn’t recall the artist’s name. If you know, fill us in.

Libby says, “I got these shoes at 9 West for a Shepard Fairey opening, and I wear them everywhere. I can go dancing in them, which says a lot.”

And there you have it! I forgot to take a photo of Libby’s closet, which is too bad, because she has an entire clothing bar dedicated just to scarves. Next time. Thanks for playing model for me Libby, you’re a peach.