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!

Pages: 1 2See entire article on one page

has written 34 articles for us.


  1. 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.

  2. 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.

Contribute to the conversation...

Yay! You've decided to leave a comment. That's fantastic. Please keep in mind that comments are moderated by the guidelines laid out in our comment policy. Let's have a personal and meaningful conversation and thanks for stopping by!