Boots For Your Masculine-of-Center Feet

Can you feel that? It’s starting to get chilly outside. Or, maybe it’s not and will never get that cold where you live, but you’re starting to experience the I-love-winter-fashion-flurries in your stomach. Either way, it’s time to have the winter boots conversation.

I know. It seems as if femmes have an infinite number of options when it comes to winter boots. But, there is life beyond the Doc Marten for masculine-of-center genderqueers, lesbians, and trans men. Yes, Doc Martens are a staple and of course they made our list of recommended boots, but the dapperQ team is here to help you diversify your boot collection. If you need a refresher course before we start, visit Autostraddle’s Boots 101.

Size and Fit

dapperQ readers often ask us where they can find masculine shoes that fit. For boots, Anita Dolce Vita recommends:

+ Fashion search engines, such as ShopStyle, which allow you to browse hundreds of thousands of products from stores and brands all over the world. Begin your shoe search by entering keywords (in this case motorcycle boots, Chelsea boots, chukka boots, etc.) in the search query boxes. You can then narrow your results by gender and size depending on your preference. You’ll be surprised at the range of sizes you can find, even as small as size 4, depending on the style. carries boots that can add up to 4 inches in height. Sizes come in men’s 6-12 (women’s 8-14).

+ Of course, if you wear a women’s size 9 or up, you have a bit more flexibility, as many men’s sizes start at around 7, which converts to about a size 9 in women’s.


The Dress Boot

Anita Dolce Vita recommends: If you’ve been invited to a winter wedding, have a job that calls for business attire, or are simply the so-fresh-and-so-clean-clean-24/7 type, dress boots are a slightly warmer and drier alternative to dress shoes because they at least cover your ankles. You can opt for a traditional dress boot that laces up, a monk strap boot, or try the slim silhouette Chelsea boot (aka dealer boot), which has elastic side panels known as gorings. While dress boots are nice enough to wear in lieu of “low top” dress shoes, keep in mind that they work best with more tailored, slim-fit looks.

My picks are the Dune Paddington studded ankle boots (ASOS; women’s sizes 5-10); RENATTA JOP ankle boots (YOOX; women’s sizes 6-10); Ecote Metal Chelsea boot (Urban Outfitters; women’s sizes 6-10); Athens leather Chelsea boot (ASOS; women’s sizes 5-10); Luca Valentini ankle boots (YOOX; women’s sizes 5-11); and Ella tan derby boots (Grenson; women’s sizes UK 3-9).

Rocco Katastrophe in dress boots. via: dapperQ

Ariel recommends: For dress boots, slim pants are a must. These are glam rock/rock-and-roll boots and you have to play the part. Cheaper brands include Bostonian (about $100 on their website) and Bass (I found sale prices as low as $70); the sky is the limit with these guys.

Sam in dress boots. Photo by Candice Comisi via: dapperQ

Tk recommends: My top pick is Tommy Hilfiger’s Runway Double Monk Cadet boot. Also, Paul Smith’s Salinger Chelsea Spectator boot and Aldo’s Draney boot. However, there are limited size options in these styles (men’s size 7.5+ = women’s size 9.5 and up).

Menswear Dress Boots in dapperQ Sizes
Click the image for pricing and availability

The Rugged Work (Inspired) Boot

Anita Dolce Vita recommends: Just as there is life beyond the Doc Marten when it comes to the combat boot, there is life beyond the classic tan Timberland when it comes to the work boot. I really like the Georgia G31 Work Lacer with kiltie accent (women’s sizes 5-10) and ASOS Amber lace-up (women’s sizes 5-10). Wear these work boots with your pants cuffed (like Tiq below), roll your pants up a bit higher to show a little sock or keep your boots slightly unlaced and bunch up your pants for a slouchy feel.

Tiq Milan in work boots. Photo by Vito Fun via: dapperQ

Mr. Rachel Tutera recommends: My top pick is the rugged-looking Timberland Earthkeepers City-Zip boot, which are environmentally friendly, but sizes start at a men’s size 7 and up (women’s size 9+).

Rugged American Work Boots

The Motorcycle or Engineer Boot

Motorcycle and biker boots. Photo by Juliana Wigmore via: Queer Fashion 101

Ariel recommends: Cleaning out the closet at my lez job, I once found a pair of motorcycle boots in perfect condition. I took it as a sign from the lez gods (goddesses?) that I was doing the right thing and have worn them for years. These are big, sturdy boots, and I love them; they can stand up to a wider-leg jean without getting lost.

The Frye Harness boot is an absolute classic (and $300); the boots gifted to me from the lez goddesses were Chippewa. Harley-Davidson, unsurprisingly, makes motorcycle boots, and they run in the $100-$150 range. This is the kind of shoe you might actually wear for the next 10 years; it might be worth it to save up some money and buy nice.

Anita Dolce Vita recommends: Second what Ariel says. Additionally, Dirty Laundry has a Showstopper motorcycle boot that is relatively affordable ($64), but they will certainly not be the same quality as Frye. DV and ASOS carry ankle length biker inspired boots that can pass for dressier shoes under nice trousers, but are still biker enough to wear to a dive bar.

Kawan(a) Shane recommends: The Harley Davidson Men’s Constrictor is my boot of choice! Whether you are out on the town sportin’ your favorite broken-in jeans, ready to ride with the pack or elevating your business casual attire, this boot is beyond versatile and comfortable. Some of the major pluses about this boot include: full-length sock lining to avoid boot-sock tug-a-war, the decorative but robust ankle harness strap for support, a sturdy zipper and most importantly, the boot comes in classic badass black or rustic brown- colors made for anyone who wants to get their swag on. The boot runs in men’s sizing ranging from size 7 to 13 and the width runs in medium. For those who may need wide width, you may try going up a half to full size according to your comfort level. In addition, the best about these boots is their price! C’mon, who doesn’t see the value in a pair of quality Harley Davidson’s for $140.00US-$160.00US? You gotta’ heart these motorbabies.

Motorcycle and Biker Boots

Next: Combat boots,  snow boots, chukka boots, and western boots!

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DapperQ is one of the world’s most widely read digital queer style magazines and is a preeminent voice in queer fashion and beauty. We inspire people of all sexual orientations, gender identities, and gender presentations to think differently about both queer fashion and beauty as art and visual activism, and ultimately have a deeper, more fulfilling relationship with style. In the words of founder Anita Dolce Vita, “dapperQ is a queer fashion revolution, one of the most stylish forms of protest of our generation.”

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  1. I just wanted to disagree strongly that cowboy boots are impractical! I wear mine all the time in rain/snow/sleet and they are wonderful.

    I should also add that they are coral pink, so maybe my idea of practical is bit, ummm, different than this post’s, as “heels lower than 3 inches” is also a qualification for practical. Retiring to my femme corner now.

  2. My problem with boots is two-fold:

    1. I have really muscular calves. The problem with knee-high boots is obvious, but also! boots that are meant to hit just below my calves most often make my legs look like un-curvaceous trees. So I usually have to go with wide-calf tall boots or ankle boots.

    2. I have an unusually high instep. This is a problem often with pull-on boots, but often means I can’t buy boots online since that isn’t a measurement they give. Unless someone with similar feet happens to have written a review and mentions it. Bah.

    But I love boots! And I love all of these boots! I may be feminine-of-center in most of my wardrobe, but my feet are totes masculine. Time for a trip to DSW!

    • “I may be feminine-of-center in most of my wardrobe, but my feet are totes masculine”

      Me too :)

    • Four :)

      I also like to disagree that chunky boots are too overwhelming on teeny, tiny girls because that´s never the case. It´s always super cute. Always! Especially with flowery dresses, rain coats, skinny jeans, boifriend jeans, cargo pants, hot pants and actually everything I can think of – no matter if on femmes or androgynous ladys.

      • Shit yes. I break fashion rules constantly, and this is one of the main ones I like to give the finger to. :)

        • Oh no! I was not trying to “you shouldn’t wear…” anyone. My girl just personally doesn’t like the way chunky boots look/feel on her own body and felt left out of the whole combat boot wearing thing until she found slimmer options. I was giving advice for folks who have the same complaint, but not saying teeny, tiny girls absolutely shouldn’t wear chunky shoes. If you like it, I love it!

  3. I’m constantly surprised that people regard Doc Martens as a “gay thing”, since I go to this weird, artsy shool where every. single. person. owns a pair of Doc Martens. Good school?

    • The day that I found a brand-new-still-in-the-box pair of blue docs at a thrift store for $25, I nearly shat my pants. Plus, they were in my size! I LOVE DOCS. I am basically obsessed. I also have a pair of velvet ones (which probably aren’t practical at all) and a few other pairs but that’s because I often get lost and end up on the l on my way to the Dr. Marten’s store in Chicago…

    • I live in Europe (Poland) and anybody in this goddammit country would regard that docs are gay. NEVER. EVER. In my totally straight school (for 400 people only me and my girlfriend were gay) it was maybe 3/4 of students wearing classic martens (or maybe 3/4 of my school were secretly gay and I don’t know about it :P).

      But this year I was in Berlin on German course with bunch of New Yorkers and I wore docs once without saying them anything. They quickly outed me ‘Oh, so you are lesbian, Barbara? – Yup, but how do you know? – Anybody who wears docs is gaaay’. I. WAS. TOTALLY. SHOCKED. Maybe it’s kinda west coast’s belief or something. If it’s true I’m ultra lezzie girl with my six pairs of martens.

    • I’m from Ireland and would have always thought of them as kinda artsy rather than gay, specially the brightly coloured ones.

    • Yeah I have to admit I’ve always thought of them as being more of an arty/hipster shoe than gay… I’m at art school at the moment and I see loads around, but having said that the only students with Docs popping into my mind are girls with cool sweaters and ALHs. I honestly don’t know if that’s a bias in who’s wearing the shoes or a bias in who I’m looking at!

      In any case, I think I might be asking for a pair for Christmas this year…

    • I mostly just associate them with Daria and am constantly surprised they haven’t made their way into my wardrobe yet.

  4. my winter look this year (and most of the year) is city-bound adirondack guide/lumberjack, so I’ve got an arsenal of work boots and vintage hiking boots that make me look fantabulous. when it comes to boots, you will see very high prices but please remember it is an INVESTMENT – if you buy cheap boots, they will not last and they will not keep your feet in good shape, especially if you’re in a high pedestrian area and walking everywhere (lookin’ at you, city dwellers). i have bought way too many pairs of h&m and asos boots that looked fantastic but lasted me a few months tops. and i expected that with a $20 price tag, but still. go for quality so you can wear them for multiple seasons without worrying about their wear and tear!

  5. I have 4 pairs of boots to match the seasons. Vintage brown leather Docs, brown leather Clark’s Desert Boots, brown leather insulated hiking boots, and army green canvas combat boots.

    There is never a time where boots are not appropriate. So many different ways to wear them!

    Also, as someone with smaller feet, I suggest trying brands like Bass and Clark that a) make boys shoes identical to men’s and/or 2) make women’s shoes identical to men’s. I have many pairs of shoes in general that I have found that way. A bonus is that kids shoes cost less, too!

  6. Yes! Blundstones. These are amazing boots. You can get them in a few different colours, and there are different styles, too. I got the “chisel toe” style, so it has a slightly dressier feel than the rounded toe, and I wear these everywhere: grad school, work, bar, etc. And plus, for rainy-but-milder places (I’m from Vancouver) they are a great fall-into-winter boot because they protect your puddies from the rain while not overheating them, as big fur lined boots can sometimes do.

    • I was thinking about it, and I completely betrayed that I only really go to three places, didn’t I? Oh well. My Blunnies get me out and back again. :)

      • I totally wear my blundstones almost every day. To the same locations. In Vancouver. Are we the same person? (laughing)

        I have two pairs – one run down, and one “fancy”/unscuffed. They are my “dress shoes” when I see counselling clients as a grad student.

        In Vancouver at least they come across as being really gay, but also really artsy, hipster-ish, etc.

        • Blundstones, for sure. Comfortable, good looking, practical, and well made. You can stomp through soggy Vancouver puddles with those babies.

  7. I went to visit an all-girls school near Boston just recently (Wellesley, woo!), and I got to sing in one of their acappella groups. I was just enjoying myself when this amazingly sexy butch girl swaggers in with her, of course, work boots on. I died. I might be ultra femme but I’m thinking I need some boots as of about yesterday.
    We shared music, by the way.

  8. Aww.
    And boots.
    Pictures of girls – in – boots.
    Feels like it´s sexy sunday already.

    *swoon & melt away*

  9. I just wish guys boots/shoes came in my size!!
    I can go into about a million female shoe stores and not find one style that I would wear, but I walk into a men shoes store and swoon over nearly every pair. But do you think anything fits me without making my feet look like snow shoes? Nope…

    Someone really needs to open a chain of lesbian clothing stores…
    Boi style with female fit!

  10. If you absolutely cannot find boots in your size, military supply companies may be able to find you boots in your size, as the military has to be able to outfit *everyone*. They are not so much with the fashionable options, though.

    Cole Haan just came out with ladies wingtips, and though they aren’t boots (they have chukkas, whhich are almost boots?), they definitely appeal to my desire for less-femmey shoes. Soo pricey, though.
    ( )

  11. Great article! I wonder if anyone has suggestions for vegans who do not wear leather? I have had a difficult time finding vegan boots that are not hundreds of dollars. I know Doc Martins have one pair of vegan boots…may have to give them a try. Thanks for any suggestions! :-)

    • Oh and I know Palladium Boots makes canvas/rubber boots but I have read some reviews saying they are uncomfortable. Anyone have experience with them?

    • Vegan options here…but they are UK based. I’ve just ordered a pair and they even ask you to send over an outline of your feet before they make them up…just to be sure you are getting the right fit.

    • Yep, the Brits have the market cornered on vegan boots. (I rue the day Gripfast stopped making their vegan steeltoes.) I have a pair of these in black and they’re great! Not designed for heavy snow or anything, but you can use regular waterproofing spray on them and they’re ridiculously comfortable. Took no time to break in or anything — and they’re sleek enough to look good with nicer pants, too (or would if, in my case, I hadn’t worn them hiking a bunch of times and scuffed them all up). Recommended!

      If anyone has non-leather serious snowboot ideas that aren’t 100% hideous, also, gimme gimme!

  12. I will let you in on a little secret. As I travel the world, you often see me wearing flats or a tiny heel, but when the cameras come off, I love to rock my studded boots! Ever since I had lunch with Lil’ Wayne, I have been sold on the studded shoes. Perhaps I will reveal a lil somethin when I land in Australia today!

  13. I am soon to be in dire need of actual winter boots, this article is most likely going to make me spend too much money and end up with all the boots

  14. Once upon a time, I saw this girl wearing the most amazing boots ever. They were black, about mid- calf, but so slouchy that they sort of hung around the ankles, and made of a leather looking material. They were cuffed in a way that makes you think of pirate boots, and they had the ring and three straps of motorcycle boots. She had decorated them with sea shells on one boot and a bandana on the other. I’ve wanted them ever since, but haven’t been able to find them ANYWHERE :(.

  15. In a full-on boot hunt right now. Thanks for helping! I did get a hot pair of ‘fashionable doc’s’ last winter, but they were so uncomfortable, I had to send them back. I used to live in Doc Martins and Fluevogs back in the day. I love the little wingtips above to.
    Most importantly, you have DJ WHITNEY DAY in the house!!! Love her!
    When is that interview/article coming out? Seriously…Ladies, get on that – before or after her blow out at The Park on Thanksgiving Eve.

  16. Oh! I have those Frye’s! Last set of pictures, third column, second row. In that height and colour and everything. I got them at a consignment shop for 50 bucks, after eyeing the Frye website for months and months and trying to convince myself to spend 200+ on boots. They’re not actually super stompy huge, unlike the rest of the boots in that photo set– they actually make my womens 11 feet look narrow and svelte. I love them tho, I wear them with jeans as soon as the temp starts to drop.

  17. I’m pretty I need most of these shoes in my life.

    I have been blessed with large feet and I currently have a beautiful pair of grey suede desert boots, made by hush puppies, that suit my chukka needs (mostly.) I’d also give a shout out to the new line of converse boots, of which I own a pair. They’re warm, waterproof, and still look like converse, just with thick laces and soles.

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