Boots For Your Masculine-of-Center Feet

The Military or Combat Boot

DJ Whitney Day in military inspired boots. Photo by Kevin Thomas Garcia

Anita Dolce Vita: My girl is not a fan of the traditional combat boot; she is short and super thin and feels that her frame is overwhelmed by their chunkiness. For those who have similar complaints, I recommend modern, military inspired versions, such as Steve Madden’s Tarney, Ladiluck, and Jaax (women’s sizes 5.5-10); ALDO’s Hoffine (women’s sizes 5-11); and Seychelles Jungle two-toned boots (women’s sizes 6-9.5). These types of boots have thinner soles and often times come with really cool embellishments like rock-n-roll studding or knit legwarmers. However, these boots may lack the durability of a classic Doc Marten. Doc Marten does have some pretty dapper boots out this season, including their Pendletons (women’s sizes 5-11), which have a decorative woven-wool side panel.

Whether you go classic or reinvented, military boots look best with pants that are bunched/cuffed or directly tucked into the boot. Add a tailored peacoat for a dapper look or a leather jacket for an urban chic look.

Ariel recommends: The Doc Marten has been my #1 boot in this department for years — since I was 16 and putting glitter nail polish on the soles. I’ve had my current pair patched and resoled and they are still my go-to when I need to climb around in a theater or do some muck work around the house…or look tough and casual even while I’m working the nerd. They’re total classics. I like the 10-eye cap toe; I think the toe detail gives them a little more versatility.

Your local army-navy surplus store probably has these in a wide variety of styles and they’re probably cheaper than civilian brands. They’ll also generally have a huge variety of sizes.

Combat boots. via: Framing Doors

Joelle Zigman recommends: Is it sad that when I saw this masculine boot idea for the first time and the first thing I thought was Doc Marten? Then I was like, “Nah, that’s too gay for words.” Thanks, Ariel, for the vindication.

The Cold Weather & Snow Boot

Duck boots. via: GQ

Ariel recommends: For days where I can remain stylish, the L.L. Bean Duck Boot is my boot of choice. I like them unlined because I can adjust my socks accordingly. For days where it is sheer snow utilitarianism, I love these giant Kamik boots I got on clearance at Zappos. They are heavy and they won’t take any crap from snow. Tuck your pants in and go for a run (a very slow, heavy-booted run). I imagine these boots will outlast me.

Mr. Rachel Tutera recommends: I like Blundstones as a winter option for folks who are in the mood to take a break from wearing duck boots. There’s the classic weather-proof Blundstone (aka Blunnies), which, although Australian sizing is complicated, come in sizes smaller than a men’s 7. Since they’re pretty unisex-looking, folks can order a women’s pair, which come in as small as a 6. They’re expensive, but they’ll also keep your feet warm and dry and last you at least half your lifetime. There’s also this Timberland Earthkeepers Alpine boot which can be a hiking boot or a winter boot. As always experimentation with lace color is an option; most commonly people have red laces on this style.

Anita Dolce Vita recommends: I’m a stickler about investing in a quality winter boot. The North Face Snowtropolis boot is pricey, but a stylish alternative to a duck boot. These can be dressed up or down, dapper (with fancy trousers and a bow tie) or hipster (with skinny jeans and a leather jacket). Keens Snowmass leather waterproof boots are half the price and are versatile as well.

The Desert Boot & The Chukka Boot

Anita Dolce Vita recommends: As Put This On says, “All desert boots are chukkas, not all chukkas are desert boots.” We could write a thesis on any one style of shoe, but in short:

+ Desert boots = soft (usually suede) lace-up with a crepe rubber sole.

+ Chukka boots = more substantial lace-up with a leather sole.

Anna Barsan in chukka boots and invisible socks. Photo by Blake Barsan via: dapperQ

Yes, Clarks have given the chukka/desert boot a bad name. But, in my opinion, the style of these boots is not the problem; the problem is the way outfits have been traditionally styled around these boots. Desert/chukkas boots can be downright super-duper dandy urban preppy and are perfect for masculine presenting folks who want a comfortable shoe option that is dressier than a sneaker. You can wear desert/chukka boots with a pair of dandy socks (see how to rock patterned socks here) or, if you live in a warmer climate, you can still get to play around with some fall/winter fashion by ditching the thicker socks and wearing a pair Falke’s invisible socks instead.

Desert Boot with socks. via: Weavers Door

For a more rugged look, try a thicker, more substantial chukka boot. Either way, I think chukka/desert books look best when your pants are cuffed/rolled up.

Mr. Rachel Tutera. via: dapperQ

Ariel recommends: I have been learning about the chukka this year as I consider my winter shoe options. I am not a huge fan of the classic chukka (think Clark’s Desert Boot, the shoe that started it all), but I like the kind with the embroidered/raised toe. These are great casual shoes, and if you play it right they can also go well with a blazer and nicer pants.

Mr. Rachel Tutera recommends: I’m really into the Timberland 7 Eye Chukkas (smallest size is men’s 7, which is a women’s 9). They come in two handsome colors.

The Cowboy Boot

Cowboy boots give a vintage inspired, frontier vibe. via: Jeremy and Kathleen

Joelle Zigman recommends: As dapperQ’s resident Texan, I have to say that western boots are probably the least practical of all the boots. They are not well-suited for rain or snow or even keeping you warm. But if you’re on the short side they might add a few extra inches of height, as well as some sexy Cowboi appeal. You could probably devote your whole life to the art of buying western boots (and several people do), because there are so many factors involved. You can make them out of the hide of any animal from eel to ostrich to rattlesnake to buffalo (for the animal lovers out there, Charlotte Russe has a decent, $43 faux-leather boot in women’s sizes 5-11). They come in pointed, square, or round toe. They can be anywhere from 3″-15″ tall. They have a price ceiling of tens of thousands of dollars for a custom boot, and a solid pair of top-of-the-line Stetson boots can run you anywhere between $300-500, which is a little impractical for a baby butch like me.

But here’s the thing about western boots: they are beautiful. Stitching is an art-form. A western boot should feel like a work of art and should be worn as such. That’s why I’m not gonna recommend one single boot. The boot should be an expression of your tastes, and your style, so play around. The best way to find your perfect fit is to go to a boot store, but since those are hard to come by on the coasts, I’m a big fan of Sheplers. Don’t be afraid to buy kid’s shoes if the men’s shoe sizes are too big. Leather boots stretch over time so it’s advisable to buy them a bit snug.

Also, dust is a Cowboi’s worst enemy. Dust on western boots can settle into the crevices and wear down the leather over time. So please, wipe off your boots every time you take them off.

Anita Dolce Vita recommends: As a native New Mexican, I agree with everything Joelle said. Growing up in the 505, there was never a short of cowboy boot stores that catered to the Southwestern styles. When I moved to NYC in 1999, I had to get accustomed to urban interpretations of western footwear.

Modern urban cowboy look. Via: Outrageous

If you want to pull off an urban version but are not into the classic cowboy boot, try ankle length cowboy boots with city touches, like punk studding.