Style Thief: How To Dress Like Jenna Lyons

Welcome to the second installment of Style Thief, where I steal the clothes off queer style icons’ backs. Metaphorically, that is. I’ll try figure out just exactly what makes queer style icons tick by breaking down their look into itty bitty bite size pieces. I get a lot of questions about how to look like different celebrities/characters, so I’m finally tackling the question “How the hell do I dress like that?”

Header by Rory Midhani

Today I’ll be stealing the clothes off my personal style guru, Jenna Lyons. Lyons is the president and creative director of J. Crew which, if you’ve been playing at home you know, is my most favoritest store. While Lyons only “officially” came out recently while receiving the “Fashion Original” title at Glamour Magazine’s Women of the Year awards ceremony, she has been a lesbian style icon ever since J. Crew started showing all that plaid.


I’d like to say that to steal Lyons’s look all you’d have to do is go to J. Crew and put on whatever they’ve got the mannequin in these days. Unfortunately, Lyons’s manages to be even more chic than her own line. Plus you can totally find Lyons’s style clothing at other (cheaper) stores.

The first step to dressing like Jenna Lyons is to roll your pants up. I sometimes wonder if Lyons has some sort of reverse circulatory problem where her ankles are hot all the time. They are constantly on display. It may also be that at six feet tall that’s just how pants fit Lyons. Regardless, you want a straight leg or slightly skinny jean that either hits or is rolled to a couple of inches above your ankle.


Next, you’ll need a button-up shirt buttoned all the way up. Yes, all the way up. Lyons’s look is all about pulling elements of traditionally masculine and feminine fashion together, and one of her favorite ways it by buttoning her shirts all the way up. As someone who is busty, I find this most do-able if I wear the thinnest, least push-up bra possible and enact the assistance of a couple of pins. If you can’t make a button-up work, Lyons’s next go-to is a boatneck horizontal striped blouse. Your blouse can even be a flowy button-up with a rounded collar.

Now that you have your pants and shirt sorted out, you have two options. You can either tuck that shirt in sans belt (I know, breaking all the rules) or leave it untucked and throw on a blazer or jean jacket. While Lyons will occasionally tucks with a jacket or untucks solo, it’s somewhat rare.


Lyon keeps her accessories bold in some ways and toned down in others. She keeps her jewelry generally muted and usually opts for a gold watch and gold bracelet. Going without earrings or a necklace often allows Lyons to spotlight other elements of her outfits.

For shoes, Lyons frequently rocks a pair of round or point toe pumps in either a metallic or bright color. While I rarely say that high heels are a signature necessity of a certain look, I think Lyons’s are a key compliment to her frequently bare ankles.


In my opinion, Lyons’s signature detail is her seemingly unchanging nerd glasses. I love these. The big dark frames compliment Lyons’s tendency to go for pink tones by tempering down some of the femminess. They say, “Oh you don’t think big glasses make girls look ‘pretty’ enough? Well fortunately they make me look fucking awesome.” Warby Parker is a great place to look for inexpensive frames, and they have tons of strong tortoise shell options.

If my take isn’t quite enough for you, listen to Lyons herself talk about this year’s J. Crew line. Beware, there’s a 50% chance you’ll fall in love.

If there’s a queer style icon you’d like to see stripped down in Style Thief, send me an ASS messageask on my formspring, or tweet me @Ohheyitslizz

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Lizz is a consumer, lover and writer of all things pop culture and the Fashion/Style Editor at She is also full time medical student at Brown University in Providence, RI. You can find her on the twitter, the tumblr or even on the instagram.

Lizz has written 261 articles for us.


  1. My love for Jenna Lyons cannot be quantified. She always looks so chic in outfits that would make me look like the dumpiest girl on the block. Ever since she acknowledged her partner at Glamour’s WOTY Awards, she is kind of my lesbian fashion hero (funnily enough, I’m not really sure there are that many contenders anyway, which is just sad).

  2. I got the J Crew fall catalog several weeks ago and fell in love with everything in there. And I love a good patterned button-up shirt. It’s unfortunate that J. Crew is usually out of my grad school student budget.

  3. I’m gonna be honest here, I’ve read the article three times, and I still can’t see a thing she’s wearing… Those hipster glasses are sucking in my vision, like a prescription black hole

    • wait shelly now that i see photos of her i feel like you two resemble each other
      like really really resemble like possibly doppelgänger

      i’m into it!

      • It doesnt help that my entire wardrobe consists of Jcrew both Mens and Womens attire!

        And Ill take that compliment and channel Jenna for the rest of the day!

  4. I was on my phone, scrolling through these pictures, and I thought: “Dang! That woman looks like she’s out of a J.Crew catalogue, but better! Where can I find these outfits…?” It all makes sense now that I’ve sat down to read the article. By the way, J.Crew offers a 15% off student discount-if you can scrounge up an old college ID.

  5. Fear not! Those of us without strikingly long/thin legs also can rock the short pants. You just have to find the length that works on you (Mine is showing everything but the actual ankle) especially if you’re curvier and your pants are straight cut or kinda skinny (it balances your leg without adding unnecessary curvature or fabric, and also shows off your sexy shape!)
    Especially with heels.
    Chic Chic Chic I love this woman.

  6. i came here to tell you how much i love jcrew
    also, the boys in that video look so sharp i want all their clothes

  7. For a woman who’s 6′ tall (we’re the same height) you’d think she could actually make clothes for women that tall which actually fit. J. Crews ‘tall sizes’ are for women who are 5’8″-5’9″ at best, not actually tall freaks such as myself. I may not buy her clothes anymore (I’ve been burned), but good for her for coming out.

    • That’s too bad. I’ve actually heard Lyons say she has to get all her clothes tailored. I would ask in the store though, some of them do tailoring for free in house.

    • Really?
      Im 6’1 and I can wear their Jeans.
      I order the Matchstick Talls and always check the inseam.
      It has to be at least 35″

      • Shelly, they’ve recently gone to some 36″ inseams (which is what I need) but not on most of their pants which are more often 34.” Most of their sweaters and jackets are too small for most women over 5’10” and can’t even be tailored to fit (which has to do with not only the extra material needed but how they place seams and do the construction). Also, if you look at their site, they have way fewer choices for tall women’s clothes than they did 5-6 years ago. Jeans are nice, but they aren’t an entire wardrobe. I actually find The Gap and B. Republic way, way better about this than J. Crew and their clothes more thoughtfully reimagined for tall bodies. But, I understand, it’s all a numbers game and business in terms of who they market for.

        • You’re Right!
          There used to be a ton more tall sizes years ago.
          I love Gap Jeans, I swear by them. And they have a sweet 36″ inseam. I do love Jcrews chinos for work though. I got a pair of 36″ inseams and they fit well.
          and I dont do a lot of their women’s shirts because they end up being to wide, when in actuality I need length. You’re totally right!
          Call me a butch, but for collared shirts and sweaters, I wear Men’s extra small slim from Jcrew and they fit like a glove! The perfect length and even look tailored. Ill have to check out banana I havent been their in ages!
          Thanks for the Tip

  8. you guys you guys if you’re looking for inexpensive glasses, has a deal going on where your first pair from them is free. disclaimer: I have not ordered from them ever, but I have heard good things which is why i have several styles open in tabs right now!

    • I’m wearing a pair of Derek Cardigan glasses right now, and they’re actually pretty awesome. If you need prescription lenses but your eyes aren’t too bad, you can get away with getting the basic (aka free) lenses, especially if your frames are chunky plastic.

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