How to Dress Like a Girlfriend

Girlfriends shaped me more than Sex and the City ever could've.

Before I decided to write this article, I sat at my MacBook for days trying to figure out where to begin on a similar one: How to Dress Like Sex (and the City). Don’t get me wrong, I’ve loved SATC since the first time I watched a heavily censored rerun of it on TBS. But, I’m a Black girl. As much as I adore Samantha, and still look to Carrie as a style inspiration (also, Miranda and Charlotte are there), they just weren’t who I looked up to during my formative years. Plus, I didn’t have TBS in my room, which meant I had to sneak and watch the New York girls cut up on the rare occasions my mom left me at home alone. You know what I did have in my room, though? UPN. Which meant unfettered access to the true style icons of my youth: Joan Clayton, Toni Childs, Lynn Searcy and, Maya Wilkes, aka, the Girlfriends. 

I can pinpoint exactly where each of the real fabulous four influenced my style, even throughout my many phases as a teenager and to this day as an almost 30 year old woman. While most of their outfits were definitely a product of the time in which they were worn (that is, the very early 2000s), the individual elements and overall vibes could absolutely be adopted for the Roaring 2020s. And yes, I will tell you how.

JOAN CLAYTON

If I were to draw parallels between the Girlfriends and their Sex and the City counterparts, the obvious and most fitting first comparison would be Joan and Carrie Bradshaw. While they are both wildly flawed protagonists, they also have the most eclectic wardrobes of their respective casts, with a rich mix of both high end brands and unique vintage pieces. Outside of the more traditional office attire we frequently saw her in, Joan’s style off the clock was chic but still relaxed, with a particular affinity for rich greens, backless tops and dresses, and crop tops. 

Over the show, especially once she opened The J-Spot, Joan’s style grew more feminine, with A-line dresses, bright pinks and stiletto heels becoming sort of her uniform. For more of the OG Joan look—which, according to Tracee Ellis Ross, was mainly made up of clothing from her own personal wardrobe as the initial budget for Girlfriends was so small—I would focus on adding muted and earth tones to my closet, with plenty of soft, drape-y jerseys and rich knits, paired with pants (especially denim and cargo pants) and go comb some thrift stores for vintage golden and wooden jewelry like bangle bracelets and arm cuffs. If you can’t do the backless + plunging neckline combo like Tracee Ellis Ross can (this is for my busty gals), I would instead opt for more sleek crop tops with cowl necks and tie details, but, don’t shy away from a visible black bra, especially under a ruffled chiffon/see through top—something our girl Joan has in common with Miss Bradshaw. Think simple but sexy, classic silhouettes, smooth textures and laidback luxury. Brands like Staud and Cult Gaia would definitely be in the 2021 version of 2000 Joan’s closet. 

For restaurant owner Joan, dresses reign supreme. Floaty skirts, statement sleeves and midi lengths in brighter colors and a surprising amount of florals are more characteristic of seasons 5 and beyond. Look at designers like Zimmerman, Acler, and Diane Von Furstenberg for inspiration. 

TONI CHILDS

Antoinette Marie Childs. If Samantha is the understood “real star” of Sex and the City, Toni is, by far, the true icon of Girlfriends. I won’t get into her problematic and downright toxic ideas and traits here—you’ve watched the show—I’m just here to talk about the fashions. 

Business casual with a dash of sex. That’s how I’d describe Toni’s style. While her wardrobe didn’t necessarily evolve in the same way as Joan’s (there’s a sort of symbolism in there), she does have a lot more moments of “fun” before mellowing out (as much as Toni could “mellow out”) in the end. For the monochrome queen in the earlier seasons, I would lean toward lightweight sheer blouses, unique prints on form fitting tank tops, and sexy, body skimming dresses in bright colors. Many of her looks could easily be thrifted, but, also, Fleur Du Mal and Rat & Boa are great places to start for even higher end versions.

As time passes on the show, however, and Toni grows into not only a business woman, but also a wife and mother (however ill-fated each of those roles may have been), her business casual looks get a bit more business, at least for a moment. Think well-tailored suits in both neutrals and bright colors, turtleneck sweaters, and plenty of wrap-style tops. 

LYNN SEARCY

Growing up watching Girlfriends, I always thought I would end up with a life closest to Lynn’s, or, at least a wardrobe. I was wrong on both counts. However, while Joan’s effortless femininity and Toni’s sexy sophistication certainly both inform my style sensibilities, today, Lynn is still the one closest to my heart.

I didn’t get to see a lot of “alternative” Black girls in my youth—one could argue there still aren’t many--so Lynn was a sort of forbidden fruit. Like Mona from Half & Half (I’ll talk about her at length in a future article), Lynn had this sort of edgy, “weird”, femininity going on, with lots of long skirts, chunky heels, and romantic details like lace and long, fluttery sleeves. Free People doesn’t tend to have a whole lot of black, which is what Lynn typically prefers to wear, but the vibes are similar, though, you know I’m gonna say you can absolutely thrift a lot of her looks. Indie designer Noctex would be a bit out of Lynn’s price range, but definitely captures her style.

Funnily enough, as the show went on and Lynn grew closer to becoming a musician—a dream she only realized after years of floundering from “career” to “career”—she actually started to dress less like the bohemian starving artist she was and more like a rock star. Go for knee high boots, edgy leather jackets, and plenty of accessories piled on top of sleek basics like the ones at The Line by K.

MAYA WILKES

Last, but far from the least, we have Miss Maya Wilkes. Every character description of Maya will describe her as an “around the way” girl whose true talent was making something out of nothing. While the plot may have made it obvious that Maya didn’t have as much as the other girls (even Lynn), her outfits sure didn’t.

I would say Maya’s style was flirty, but still very much ghetto fabulous, in the best way. She loved a short, pleated skirt, but, was also the only one to really rock jumpsuits on the show—especially denim ones. Tall boots with skirts, flirty tank tops with sleeves that still expose the upper arms, and plenty of reds and pinks define Maya’s style.

It’s hard to pinpoint brands for the 2021 version of Maya, as her style was so undeniably “Y2K” yet today’s Y2K offerings are so…wrong. However, Emily Ratajkowski’s line Inamorata has some incredibly sexy printed blouses and matching mini skirts that, paired with a pointy toe boot or lace up sandal, could be perfect, and Hanifa has some gorgeous dresses for a more luxurious version of that laid back fabulousness.

My favorite fashion moments of the entire Girlfriends series are, hands down, the opening credits. Ignoring the terrible season 8 sequence without Toni, the snippets of them walking and posing in a black abyss while Angie Stone sings about how her girls are there through thick and thin are some of the most amazing and succinct examples of how to build character through costume. The girls’ outfits are all extremely similar, much like Destiny’s Child in the days when they were styled by Tina Knowles, but perfectly distinct in ways that are unique to each one’s personality. Above, for this group promo shot, we see Toni in a classic tank and fitted jeans in a true blue, Maya with some flirty ruching on her own top, Joan in a more practical loose jean, and Lynn in a top that is a bit “younger” than the rest, with lace trim and faded baggy pants. The differences are subtle, but speak volumes about the type of woman each girlfriend is. It’s art.