How We Wear: Boots

Even the most “accessible” queer fashion can feel intimidating when you only see it on Kristen Stewart or the red carpet – that’s why we’ve assembled this group of real-life gays, lesbians, bisexuals and queers to show you how real people are wearing queer wardrobe staples and celeb-inspired fashion. Pay it forward by sharing your own look with us; who knows, be your own style icon!


Carolyn, NSFW Consultant

What are you wearing?
Mock neck crop top, jeans, boots

Where would you wear this look?
Los Angeles has destroyed my sense of what is appropriate to wear where, but places I have worn this include: bars, queer events, extremely casual meetings, and to have dinner with my parents. Key to this look is actually not anything I’m wearing at all but instead my dog photobombing in the background, adding a sense of playfulness and more importantly an explanation for the paw prints and dust adding “texture” to my jeans, which means I would most rather wear it “somewhere my dog can come too.”

Where would you shop for this?
Boots: Frye circa 2015
Pants: Madewell
Cropped mock neck: Free People
Ring: vintage

What do you like most/least about this item?
I love that I feel really hot in these boots all the time. Am I allowed to say that? I’m going for it. I also love that they make a shirt plus the exact same pair of pants I wear every single day in any context look like “an outfit.” HOWEVER I do inside of the boots secretly have quarter-inch lifts because without them my feet somehow do not make contact with the insoles in a way that means I can walk without tripping over myself. Walking and not tripping over myself is ideal, but then the boots come up just a little less high, so win/lose/etc. Also my footfall is super heavy, and I purchased these boots in 2015 and have worn them consistently as everyday footwear for two winters in a row, so what I currently like least is that I will have to get them reheeled before it is warm enough to stop wearing them every time I leave the house.

Archie, Cartoonist

What are you wearing?
Boots are knock-off Doc Martens that a pal found in a dumpster for me, note the “vegetarian shoe” on the label. Also wearing mesh shirt and a satin over-shirt –The back of the satin shirt has a picture of a fist and says “My Body Is Church And You’re Here To Worship.” SO!

Where would you wear this look?
I wore this to a coffee shop! So either day-to-day hangs or going out. Probably not an office job.

Where would you shop for this?
Anywhere Docs (or in my case very good knock-offs) are sold!

What do you like most/least about this item?
I think these boots are really versatile, they basically go with all outfits and are great for spring/fall. My least favorite thing is how slippery they are in the winter–they look like they have traction but honestly their soles just make walking harder!

Robin, A-Camp Senior Staff

What are you wearing?
I’m wearing a navy jumpsuit, minimal jewels and silver boots.

Where would you wear this look?
I would wear this out to dinner, to a chill drinks event, to a meeting with a non-corporate-y client, or to a house/dinner party. I feel like this outfit is sort of “going out” lite for me. If I wanted to dress it up, I’d probably add some more jewelry, maybe a bold lip and a real cute jacket, but it feels somewhat casual/comfy chic to me.

Where would you shop for this?
The jumpsuit I got from Alternative Apparel and the boots are from Anthropologie. Alternative Apparel is way up on my list when I need comfortable basics. I feel like Anthropologie is a little too bohemian flowy hippie for my taste but their shoes are always really elegant in a comfortable, not too trendy while still stylish way.

What do you like most/least about this item?
I love that these boots are super comfortable and cute. Metallic things generally catch a lot of attention so you get a lot of compliments. The only thing I don’t love about them is because of their unique color and pattern, they don’t really go with everything so I have to be choosey. I like wearing these boots with something simple like a dark jumpsuit/pant that falls just above the top of the boot.

Vanessa, Community Editor

What are you wearing?

I’m wearing a grey long sleeve Old Navy dress, black tights from Torrid, and Doc Martens. I’m also wearing an Earth pendant made by Beth and Warby Parker “Beckett” glasses.

Where would you wear this look?

This is very much my “winter uniform” so I would say I wear a version of this look almost every day. I wear it to school, to work, to a casual date, to dinner with friends…pretty much anywhere that isn’t explicitly “formal” or “very sexy.” I own this dress in multiple colors and fabrics – the velvet pink version is nice for a slightly more formal setting, the spandex black version is great for a hot date where you don’t want to look like you’re trying too hard, and the sleeveless version makes transitioning this look from a winter vibe to a summer scenario very easy! – and cannot recommend it enough for fat femme babes on a budget.

Where would you shop for this?
Dress from Old Navy, tights from Torrid, boots are hand-me-downs from a pal but you can obviously purchase Doc Martens at a Doc Marten store!

What do you like most/least about this item?
The thing I like most about this item is how fucking gay these boots are. I’ve wanted Doc Martens my whole adult life and for some reason I’ve never pulled the trigger and purchased them. When a friend told me this pair no longer fit him post-transition and asked if I wanted them, I felt like I’d been blessed by the queer fashion fairy. I love that they’re not black, because it makes them a little bit different from all the other black Doc Martens at the gay bar, and I love that no matter how femme my look is, I feel really fucking gay and seen when I wear these boots. The thing I like least about this item is that if I don’t wear them with tights, they give me really terrible blisters on the back of my ankles, no matter how much I break them in or what kind of sock/bandaid combo I try. I can wear them for short amounts of time with very high socks, but eventually I get a blister. I’ve never gotten a blister with them when I wear tights, so I try to think of them as specific-to-tights boots. This has been fine all winter but I think is going to bum me out come summer.

Carmen, Associate Editor

What are you wearing?

Long sleeve flannel dress (Old Navy, here’s a similar one),
plus size Black Leggings (Forever 21),
Sorel winter boots
black puffy coat,
red checkered scarf,
red winter beanie with satin lining,
oh and since Vanessa mentioned it – my glasses are also Warby Parker, style “Louise.” (I got mine in a see-through crystal color that is no longer available, but this rose water color is similar.)
Lipstick is Urban Decay. The color I’m wearing is discontinued, but this is a similar shaded red that I would recommend to someone with my skin tone. It’s called “Gash,” which I kind of hate, but here we are.

Where would you wear this look?

I literally took this photo outside of brunch, I guess that answers that question! This dress is one of my standbys for “casual fancy” situations; I would also wear it on a date or out with friends. I’d even wear it to my office – without the beanie – if I worked somewhere casual enough. The vibe I’m going for here is: I’m trying, but I’m not trying too hard. You know?

Where would you shop for this?

My main go-to’s for shopping are Old Navy/ the Gap, Target, and Forever 21. I’m willing to spend more on my winter outerwear than I am with my everyday clothes, because I live NORTH OF THE CANADIAN BORDER (What up, Detroit!) and I consider being warm and dry a worthwhile investment. To that point, my boots are Sorel, which admittedly can run expensive. However, I’ve worn these boots daily for five complete winters and they’re still nearly pristine. They are soft and warm and when I put them on, my toes sigh in relief.

What do you like most/least about this item?

I think sometimes it can be hard to style a clunky winter boot as a femme, so I’m proud that this look is both functional and expressive! Also, there’s something about wearing a down puffy coat with big hoop earrings that makes me feel like I’m in a Jennifer Lopez music video circa the mid-00s, and – from one Puerto Rican to another – I kind of love it.

The beanie I’m wearing in this picture is a huge find! Most winter hats are made of wool, which dries out and breaks off natural black hair. Grace Eleyae is a black woman genius who decided to start lining her wool caps in satin (ideal for dry, curly or kinky hair). That means I can be warm, look cute, AND keep my curls protected. I wear her hats almost every day and this is the very first winter that I haven’t seen any major hair breakage by February. It’s a game changer. I owe her everything.

Ok. Back to the boots, that’s what we are here for afterall. I’ve lived in epically snowy, blizzard-prone, ice temperature, winter climates my entire life. Trust me when I say this: heavy, rubber bottomed boots are a must! This is non-negotiable. I also started looking for boots with faux fur lining a few years ago, and have greatly appreciated the improvement. No matter if it’s negative 20 degrees fahrenheit or 13 inches of snow, I cannot feel it – and I like it that way. To style these boots, I’ve found it works best to lean in to the winter aesthetic. I go with soft chunky scarves that are so big they could double as blankets, thick leggings that work as tights, hats and gloves, etc. I feel like a hip hop snow bunny!

Heather Hogan, Managing Editor

What are you wearing?
Men’s L.L. Bean 8″ snow boots, Patagonia jeans, Costco flannel shirt, L.L. Bean women’s classic down jacket, Costco beanie.

Where would you wear this look?
Literally everywhere I go when there’s snow on the ground. I’d wear it for shoveling, to the doctor, to the grocery store, to the bookstore, to the pub, to the movies, to hang out with my friends, or on a non-fancy date with my partner.

Where would you shop for this?
L.L. Bean, REI, and Costco.

What do you like most/least about this item?
Growing up and spending most of my life in south, plus not being a particularly fashionable person means I didn’t even own a pair of boots until I was in my 30s. I just didn’t need them. The first winter I lived in Salt Lake City and I got a pair of snow boots, I fell in love with them because they made me feel extra dyke-y. That’s what I love most about these boots too. Plus they’re very durable. I bought them in 2013 and they’re showing no signs of being worn out. They really go with my whole “your favorite gym teacher”/“lesbian presenter on Great British Bake Off” vibe.

Riese, Editor-in-Chief

(Please also enjoy Riese’s very gay BONUS LOOK she generously provided.)

What are you wearing?
#1: Black slip dress (H&M 2016), Black Boots (American Eagle 2016)
#2: High-waisted BD jeans (Urban Outfitters 2017), black bodysuit (H&M 2017), Mossimo Boyfriend Fit Flannel (Target 2016), Black boots (American Eagle 2016)
Also in both I have CVS Gauze ($8.99) wrapped around my hand/wrist from some severe burns suffered on Saturday evening.

Where would you wear this look?
#1: To a party in Loren’s basement in 1996 / modern day equivalent
#2: To West Beverly High in 1996 / modern day equivalent (I didn’t actually go to West Beverly High but if I had a chunky black belt then this outfit would be straight out of the Kelly Taylor / Brenda Walsh playbook)

Where would you shop for this?
#1: Asos design cami slip dress ($24, asos) (also comes in plus)
#2: Black bodysuit ($9.99, H&M), Hollister oversized flannel boyfriend shirt in plaid ($34.95, asos), BDG Girlfriend High-Rise Jean: Light Wash ($69)

Boots:
Monki Lace-Up Boots in Black ($72, asos)
Doc Marten Ankle Boots ($140, Barney’s)
Frye Veronica Combat boots ($278, Shopbop)
UO Zoe Leather Combat Boots ($88, Urban Outfitters)

What do you like most/least about this item?
I cannot extract black boots from the ‘90s and place them into the present era so I have continued to dress black boots in ‘90s-style outfits my entire life. Luckily this has come back around and the ‘90s are in again. In addition to grounding these looks in a specific era they also feel very grounded in a specific location — the midwest.

I had Doc Martens that served the purpose these boots served for a while, but they gave me blisters every time I wore them and I got tired of applying moleskin to my feet every time I wanted to wear them and eventually in my most recent move it was time to say goodbye. These American Eagle boots are actually kinda shitty (whatever they’re made of has already scratched and I literally have filled in the scuff with black permanent marker) — I like boots that I can fold over, and it’s hard to find a style that’s chunky enough to make me feel like Daria without being so chunky that I look like Bigfoot, since I have giant feet. I recommended combat boots because I feel like somehow everybody else but me can wear them without pain and strife!

Boots make me feel powerful and a little mean. They’re also good for the rain.

Sarah Sarwar, Design and Marketing Director

What are you wearing?
Black Timberland Boots, my mom’s black turtleneck, and high-waisted black skinny jeans.

Where would you wear this look?
Literally anywhere and anytime. I love rocking this when I want to feel hot and powerful.

Where would you shop for this?
It’s a v basic look — skinny jeans are ubiquitous as a clothing item and turtlenecks are back in, so you can find the clothes mostly anywhere! I think I got the boots from Journey but it’s been like 6 years since I got them. They’ve held up REALLY well!

What do you like most/least about this item?
That they’re versatile and can be worn with things that involve lots of colors and patterns, or more casual jeans and tees.


These are our team’s faves; here are some suggestions to make them yours!

1 / Aldo’s Ocoamma 2 / Dr. Marten’s 1460 3 / Forever 21’s Faux Leather Ankle Boots 4 / Sorel’s Winter’s Carnival Boot 5 / LL Bean’s Bean Boots 6 / ASOS’s Monki Lace up Boots 7 / Topshop’s Brake Lace-Up Boot

What boots are you wearing to get through the last gasp of winter? Show us in the comments!

Mika is a venezuelan art director, designer, and recognized funny friend. He has previously worked at the Walker Art Center (MPLS), 2x4 (NYC) and Rumors (PDX). He is a proud father to a Cancer cat and a Gemini rabbit. You can follow him on Twitter, Instagram or check his website.

Mika has written 27 articles for us.

39 Comments

  1. I think I currently have, um, eight pairs of boots? No Doc Martens. Love the look but y’all’s comments about blistering are warning me off.

    Search “galaxy boots” on Etsy and you’ll see what I really want (lemme tell ya what I want what I really really want).

    Y’all are babes. Like every single one of these pics is some combo of cute and hot.

  2. Oooh this is a really good reminder to get myself to a cobbler! My doc martens need fixing, I need to get these Timberland boots I found for $10 resoled, and my sneakers are coming apart at the seams. eep!

    • Lol, I love this article but I was a little shocked that the majority of the boots were lace-ups. I feel like the ability to just stick your feet into a pair, zip em up and walk on looking great is a common gay sentiment? Unless the ‘I don’t have time to tie my shoelaces’ is an ADHD brain sentiment instead…

      I have a stand-by pair of chelsea boots, but I just replaced my beloved ankle boots that had a broken zipper, and I’m so excited to try them out!

      • I am so against laces. I have curly laces that I don’t have to tie up on all my running shoes. Sadly for winter I had to buy a chunky ski-bootish pair that laces up.

        Everyone around me is into Blundstone, which interests me because of the pull-on factor.

    • Here for Chelsea boots! Every weather every day. (and we get a lot of rain so that means a LOT of wax to keep them perfect). In snowy conditions I wear over-the-ankle lace-ups though, so maybe it’s a winter bias?

  3. As someone who went to what was technically West Beverly(Beverly High was touching the border of the city west of it) I can tell you Uggs, Louis Vuittonm & Forever 21 boots were big. Many paired it with Pjamas for that I just got out of bed look, but really spent 30 mintues getting ready and drove a a white BMW to school(Clueless reference that’s acurate)

  4. I currently have two pairs of boots. I have a pair of black Chelsea boots (from Naturalize) that are 9 years old and that I love. I don’t wear them for work / everyday because they have just enough of a heel to bother me if I’m standing or walking in them for several hours. But I wear them for almost every occasion where I want to feel hot or capable or gay or super cool – dates, job interviews, client meetings. They look great with my wide legged interview trousers and skinny jeans and my cargo pants both baggy and more tailored. They were a present for my 40th birthday – I turn 50 in November and I’m afraid they might not make it to my bday. The leather is starting to look a little worn.

    I’m currently wearing a pair of black “combat boots” – they are pleather and they have a side zipper, front laces and a top buckle just because. If they were a person I’d think they were trying too hard. I’m still not exactly sure why I bought them except that I tried on like a dozen black boots at the Discount Show Warehouse and I was so excited by how cute I looked in all of them and then I realized that I’d been in the store for an hour (which is long for a non-shopper like me) and I just had to get out of there. They are not bad boots but they don’t make me feel instantly fashionable like my Chelsea boots or instantly kickass like I was hoping they would.

    I like the look of Sarah’s black Timberland boots – I want something that can stand up to Chicago weather and make me feel both cute and kickass when I wear them.

  5. Enjoyed this post (and honestly all fashion-related articles on this site). As a masculine-of-center vintage clothing person, my uniform this year consists of various colours of overdyed vintage workwear on top, indigo jeans, and mirror-polished black Stacy-Adams cap-toe boots. xoxo

  6. I feel seen with all the doc shout outs! I have a short black Chelsea style and an oxblood lace up pair. I didn’t have the confidence to wear them until I started coming out! Now it’s almost everyday (except in the summer).

  7. I have two boot looks I rock. The first When I’m working around the house or out in the wood lot it Chipawa steel toe Logger boots with a 1-1/2” heel. Also handy man repellent when running into Home Depot.

    “Miss can I help you?…..oh never mind “.

    I usually pair my Chipawa boot with jeans a tee or tank and a flannel button up topped with a US WNT soccer ball cap with a pony out the back.

    The other are black clunky boots wit a couple buckle straps I wear any where else with skinny jeans maybe a long tee or tank and denim jacket.

    Riese: I hope your hand heals up.fast Carpal Tunnel? Occupational hazard ya know for lady lovin’ ladies hang in there.

    • Engineer’s boots for at the office if I want a little more confidence that day and Red Wing boots with their “King toe” which is an Osha approved crush proof toe that you can wear on a construction site that’s lighter weight than an actual steel toe when I’m visiting a job site, they’re also waterproof and insulated so I also use them as my winter boot.

  8. Ok. I love this so much! Boots have been on my mind lately and I need some help if anyone has advice!

    ~ I really want a pair of Docs but I have suuupper wide ankles and I’m afraid they won’t break in and get soft enough to not give me blisters. Any advice there? I may resort to getting the lowest cut ones I can (I already have some of their shoes and love them)

    ~ I’m moving to Chicago this year and will need some real winter boots that are warm, water proof (?), and have good traction. I’m thinking something from LL Bean?

    • Good socks are the answer to all of your problems! While my ankles have always jived with Docs’ sizing no problem, I wear high tops and ankle boots pretty much exclusively (regardless of season) and have found that thick enough socks can make breaking in even the most impractical ankle boots doable.

      Regarding the Chicago winter: I myself have a pair of Danner hiking boots (can’t recall the exact style, but on the heavy-duty end of their product spectrum) that kept my feet nice and toasty even during the Polar Vortex. But to be honest, I’ve worn my Docs + Smartwool socks pretty much daily for the past three Chicago winters with great success. I have circulation issues and my hands and feet can become huge liabilities in freezing temps, but there’s been very few days where I felt like swapping out the Docs for the Danners was necessary in order to keep all of my toes.

      • Thank you! I will definitely get some long socks before I get the Docs. I’ve also heard good things about their leather conditioner, so I’ll probably give that a try too. Will also check out Danner boots for winter! Maybe if I have a ton of great boots I’ll hate winter just a little less 😀 😀

  9. “It’s hard to find a style that’s chunky enough to make me feel like Daria without being so chunky that I look like Bigfoot, since I have giant feet.”

    Riese I hear you.
    Same issue with hiking boots, too.

    Awesome post awesome looks, thank you!

  10. Yesssssss

    I have a pair of black ankle boots I wear to work a lot, some ankle height combat-style boots that are great, and then winter boots and galoshes, which I wore today.

    I used to have Docs and I wore them a lot, but honestly, they never fit well, so I finally got rid of them, but I’m sad without them.
    Can anyone recommend good knock-offs/similar styles that have half sizes??

  11. from basically halloween through the first major defrost (read like rn) i wear my ll bean duck boots religiously. they’re warm, almost guaranteed to keep my feet dry, color coordinate with most of my wardrobe, and add that last little dash of gay! acquiring a variety doc martens is on my 2019 to do list. i’d also love to grab a pair of chelsea boots or maybe the barristers boot.

  12. Is it even legal to buy your own docs? Mine are from a former roommate circa 2013.

    I’m currently wearing them because my coworkers adamantly refuse to comment on my (tbh, absurdly unprofessional) style because they just assume it’s a queer thing. AND THEY’RE RIGHT.

  13. Hah, found a photo. Here I am in my Lesbian Ken Art Director look, which is very similar to my everyday bi art and design professor look, back when I taught. Note the Chelsea boots.

  14. My current standbys are Ralph Lauren Chelsea-style rain boots, a pair of black (well, more gray actually) wingtip lace-ups that I got like 6 years ago and have held up really well, and hiking boots. I wear one of those three pairs almost every day for ~3/4 of the year, depending on the weather.

  15. I do sometimes worry they make me look like a police agent provocateur but hey beggars can’t be choosy. They are quality shoes that were on clearance that fit my freaky ex ballerina feet and under long formal pants are passable as dress shoes but more supportive and protective.

    I really do love the solid blackness of them (docs are never 100% black) and the sound they make when I swagger tho.

  16. If you, like me, look at this list of (very cute!) boots and think “none of these boots are severe or aggressive enough for my personal taste” may I recommend the Jadon 8 Eye doc marten boots. I have had multiple people tell me that my shoes shout that I am a top and that is a successful shoe for me!!! I wear them with my typical butch uniform of sweater or button up with skinny jeans cuffed above the boot, and I have found they add just the correct amount of dirty-dyke vibes to my typical outfits.

  17. If Autostraddle was Canadian, this list would be 7 kinds of Blundstone in almost-identical styles.

    That being said, I once threw a party in Halifax and there were 20 pairs of Blundstones piled at the door, and after having to spend the next week coordinating strangers to meet up with other strangers who went home with the wrong shoes on, I went out and bought a pair of combat boots.

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