I’ll Have What She’s Wearing Returns with Jessie, a Cute Tomboy from Atlanta

This is Jessie. Jessie is a 23 year old Atlanta to Boston transplant working at the Museum of Fine Arts in Boston. When I asked her where her clothes were from she said, “Target. Everything, everyday, Target. What can I say, their pants fit me and I can afford them…I’m so ashamed of my addiction!”

Either way, if it’s Monday and this picture was taken in the Barbie section of a grocery store, then I’ll have what she’s wearing.

So what are we looking at here? Black T-Shirt, jeans and hoody (which Jessie cut the sleeves off of) faded to perfection paired with a white pocketless button-up. Jessie complements this standard outfit with plaid skate shoes and just a touch of black jewelry.

A word about button-ups: If you’re small busted like Jess, you should be able to buy a men’s slim fit button-up pretty easily. If, on the other hand, you have a bigger bust, I suggest buying a shirt where the is a button on the fullest part of your chest. This should (hopefully) keep your shirt from popping open.

$8-Target 49.50-J.Crew $51-American Apparel
$40-DKNY $50-All Saints $48-Pac Sun

It’s a simple yet definitively queer every day outfit. Yum yum.

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Lizz is a consumer, lover and writer of all things pop culture and the Fashion/Style Editor at Autostraddle.com. 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 273 articles for us.

49 Comments

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    this has been my uniform all summer. i always have a rule that you need at least one layer of pattern. usually it’s stripes underneath a solid button down or a solid t under a flannel or gingham button down.

    if you can’t afford to cut off your pant sleeves (like me) you can just roll them up just below the knee. this is great if, again like me, you have knocky or mangel up knees (too many cycling accidents) I haven’t de-sleeved a sweater yet, i’m too attached to my hoods

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      I was thinking same thing. $250 for one outfit is an awful lot even if most of it is wardrobe staples.

      On the other hand, I may need to go cut some sleeves off some old hoodies I’ve been ignoring lately.

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        Yeah, but who ever buys a whole outfit just to wear with the other things in the outfit? I figured most people probably own 3/6 of the things (or similar) but maybe hadn’t thought about putting them together like that.

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    Very cute outfit (and girl). Target, man. Gotta love Target. Love the sleeveless hoodie look, but the thought of tearing one of my hoodies or jeans is cringe-worthy.

    But if we’re talking cutting up jeans, hoodies and shirts – may I suggest your local thrift stores for some of the items? The last time I went I found a cute Coverse button up and Tommy Hilfiger button up for 90%+ off – in great condition and in my size. Do you know how hard it is to find a button up that fits a 32D and is still slim-fitting around the waist? Damn hard, that’s how hard.

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      Actually, I know exactly how hard it is to find that shirt. I’m still not convinced it exists, but J. Crew and Express have always been my best bet.

      Also, sometimes it might be worth just taking a larger shirt in at the waist.

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    Very hawt (the outfit and the girl). too bad it’s like 8 billion degrees all day every day where I live. I couldn’t even imagine wearing a hoodie and/or pants. That said, anyone know where to buy unisex/not super femmey button downs for cheap? I used to shop American Eagle but it seems they’ve lost their way…

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    Target? Urban Outfitters? c’mon guys – do you realize those places do not support gay rights?!

    and you’re supporting them by buying their products?

    there’s gotta be other places to shop that are stylish, affordable, and gay friendly….. lets get it together ladies.

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      I feel like stylish, affordable, and gay friendly are three aspects that often cancel each other out- it’s like that saying about college: there are friends, sleep, and class. You get to pick two.
      Where do you shop? I don’t mean to be rude or anything. It would just be lovely to know of places that fulfill all three requirements if you happen to know them.

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      Actually until this year Target had a Corporate Equality Index rating of 100, they only lost points because of their recent donation which was obviously business motivated (as oppose to hate motivated) which they also apologized for.

      As for Urban Outfitters/Anthropologie/Free People, although their founder, Richard Haynes, donated money to Rick Santorum (mostly in the 90s) the CEO is a gay guy so maybe it all washes out.

      Plus, regardless of the store, when you buy through autostraddle, it helps support us!

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      i don’t think you should buy your clothes according to how ethically correct a company is. you would never wear anything nice.

      por ejemplo if i wanted to buy gay friendly i could go to american apparel, but oh wait remember all those sexual harassment charges that dov charney had against him? or if i wanted some sweet diesel undies but then was like “oh no made in china!” sorry u.s. economy but i’m like a moth to bright colors, you created this mess by exporting labor so deal.

      i did buy a few items from revel&riot which were gay friendly and stylish, but my bank account defiantly took a beating. stylish, affordable, or gay-friendly pick wisely friends

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    For any tomboys, transmen, or genderqueer/masculine-of-center folks out there trying to find men’s formal wear in smaller sizes: try Express Men. Seriously, I just got suit pants and a vest there for my friend’s wedding, and it rocked my world! And way less expensive than most men’s formalwear stores.

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