This is our very dear and seriously adorable friend Rachel. Rae and I were roomies for just before Bryan and I got engaged, and fortunately for me, she’s not the sort to leave passive aggressive notes on the fridge. She’s more the subtly witty friend who never seems all that funny until you’re spraying red wine out your nose for the third time in a night. Ow.

Bryan strong-armed Rachel into becoming one of Adaptive Path’s first employees years ago, and she’s still there. I have no idea how to describe her job. She’s sort of their resident empath — advisor, bellwether, able to predict whether new policies will make everyone feel vengeful and quitty, etcetera. Rachel is the sort of person in whom it is wise to confide. She’s also a sharp dresser, and that’s really why we’re all here.

The office is casual, and Rae never looks like she’s trying too hard, which fascinates me. It’s easy to look good when you’re dressed up, harder to feel cute when you’re just going about your day, you know? This is the type of thing she’d wear to work if she had plans to head out afterward. (Like I said, the office is casual.) Her jacket is by Plus Four.

For me, good casual dressing requires a lot more effort, or more money than I want to spend on the perfect T-shirt, but Rae always seems to have pulled something over her head and tumbled out into the world looking stylish. Her dress is American Apparel.

Rae is naturally a wee tiny person, and she’s also a vegetarian who bikes everywhere — hence the ability to wear anything made by American Apparel. Her petite frame can be a big challenge when she’s looking for clothes, because she either has to shop at Gymboree or have everything tailored. Her red belt is a Goodwill score.

Her shoes are by Me Too. Rachel refuses to wear uncomfortable shoes, and more than once I’ve had to pep talk her through buying a pair of pumps for a wedding or whatnot. She’s become more open to heels over the years, but she’d like you to note that these are comfortable flats with nice, bouncy rubber soles. Noted.

She got the necklace second hand at Buffalo Exchange and the bangles were a gift from a friend who got them in Vietnam. Rae has very little jewelry, so what she does have is in heavy rotation.

Tomorrow, we’ll have a look at a work outfit for when clients are in the office.

This summer dress is Marimekko for Anthropologie, and are you seeing those pockets? I would totally make her hold my lipstick. The tank top is by Ogle.

I should mention that Margaret and I are like minded in that neither of us ever pays full price for anything. She’s one of those shoppers who checks in to her favorite shops a few dozen times so she can snag a favorite piece right when it goes on sale. Purse is Angela Adams.

Wood and shell necklace is from a boutique in Ashville, North Carolina.

These shoes are Aerosoles. Surprisingly cute, right? Plus I think she could technically bowl in them.

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Are you seeing this, Internet? This is Margaret Stewart prevailing. Right after we took these photos, she performed a brief tap number.

It would never even occur to me to purchase that vest, let alone tie it jauntily and pair it with wide-leg trousers. Also, wouldn’t it make a great maternity piece? It would. Vest is by Splendid, and the open front knit cardigan seems to be a signature piece for that brand. Trousers are from H&M.

Two-tone shoes are by Greater LA.

The necklace/collar is handmade by an artist in Buenos Aires. Margaret bought it on the street a couple years ago. You’re already plotting how to make one for yourself, aren’t you? Me too.

We took these last summer, so of course there was a romper involved. This one is from H&M. Man, rompers are really representing on Mighty Girl of late.

The side view on these kills me. Again, I think I need more interesting shoes. I lost my notes on where these came from — Margaret, let us know in comments if you remember.

This brooch was a birthday gift from me, and it’s becoming my sisterhood pin. Everyone I love gets one whenever there’s cause for celebration. It’s by Elefante è Vida, whose shop I’m always loathe to share, but Margaret has forced my hand. I would shake my fist at her, but I’m too flattered by her sweetness in wearing it. Aww, Stewart.

You may remember my friend Margaret from the Mighty Closet I did with her a few months ago. Ms. Stewart is one of my inspirations when I get dressed — she has a great eye and such a sense of fun — so when I took her photos, we did two sets. Here’s round two:

I covet this skirt. It’s so versatile and swishy.

When Margaret tried on this outfit, she wasn’t sure about the puffy Diane von Furstenberg shirt. She often pairs this skirt with a fitted black T-shirt. I felt like it depended on what she was going for; Margaret said she wasn’t sure she wanted to go for Eva Peron:

But come on. She rocks this.

The skirt is Marimekko for H&M, and it has me convinced that long skirts and T-shirts are the perfect San Francisco uniform. As User Experience Manager for You Tube, Margaret needs a lot of day to evening looks that don’t seem strange when the tech guys are still wearing sneakers at cocktail hour. Separates are the perfect option if you need to look presentable, but not overly fussy.

This antique ring is a tiny frog resting on a lilly pad. Margaret’s little girls are already fighting for ring rights.

Her versatile pointy-toe pumps are BP from Nordstrom. You may recognize them from my site banner.

The lacquer Bean Pendant is Elsa Peretti for Tiffany & Co. The hair is from God.