Boots 101: One Boot, Two Boot, Red Boot, Blue Boot, Queer Boots for Every Occasion

Welcome to winter! The one time of year where you can shamelessly bitch and moan about how cold your feet are without social repercussion. In honor of this wonderful time of year, and the fact that we’re just over half way through it, I thought I’d bring you a special treat. Ta-Da! A boot round-up!


Lets start by talking about fabric and heel. There was a time when I literally wore my chunky heeled black leather boots every single day with every single outfit. The height of the heel and the mid-range quality leather just made them versatile. This is not always the case. The height of a boot heel can range from completely flat to infinity and can be chunky or hot sexy stiletto style. Most boots you find will be in the one inch to five inch range. Both the material and the cut determine the dressiness of boots. For someone going for a more femme look, a tan mid-calf boot made of distressed leather without a heel will look daytime casual, while a black boot with a stiletto heel, a contoured ankle and a long shaft will look more appropriate for the evening. For someone going for a more butch look, a lower shaft boot with a slight heel in a black or cognac polished leather will look more dapper than a tan, chunkier heeled combat or work style boot. Generally speaking, duller or distressed leather or suede is more casual while polished leather in dark or rich colors tends to be dressier. That being said, these rules cannot be broadly applied to all boots. You really have to take it boot by boot.


When shopping, be aware that leather boots change shape and size as you wear them. Make sure that anyone helping you with boots knows what they are talking about and can help you fit properly, particularly through the toe and inseam. In fact, it might be worth brushing up on your boot terminology so you can best explain what you’re looking for. One very common boot shopping hardness is finding boots that fit around one’s calves or are comfortable on the ankles. If this is a problem for you I strongly suggest using a measuring tape to figure out the circumference at the widest part of your calf and ankle and then ordering boots online. If this freaks you out, try shopping in a specialty boot shop. In most boot shops and department stores you should be able to find boots abundantly common in black and brown, easily found in slate and tan and less commonly seen in red and blue. Both leather and suede are in style and widely available right now, although bright colors are much more common in suede. I would say the availability of colors roughly correlates with how good boots actually look in that color. The exception to this rule is slate which should be the most widely available color of boots because grey boots look fucking awesome.


Though most people have a general sense of how to wear their own personal favorite basic boot, I receive a lot of questions about particular types of boots and how best to achieve just exactly the look/formality/gender expression/awesomeness one might be going for. There also seems to be a lot of confusion about general to tuck or not to tuck. This varies greatly by boot. Thus, I’ve divided some of the most common types of boots in to categories that made sense to me at the time of writing. I’ve done my best to talk about how each particular boot might play a role within your personal style and gender expression. This list is certainly not meant to exhaustive, if it were I would have included mukluks.


Snow Boots

The thing about snow boots is that they’re the only type of boots you truly absolutely “need.” If you live in a place that gets snow, winter boots are the boot equivalent of Wikipedia. Technically you can get by without it, but it really sucks and you feel cold and alone and it ruins your day. If you don’t have a working pair of winter boots, it means you’re ruining all your other shoes and probably costing yourself tons of money and sadness. I love to wear winter boots in to work and then change in to Sperry’s/Toms/moccasins/slippers.

One of the best things about snow boots is that, since they’re only a “sometimes shoe,” you can go as simple or as crazy as you want. You can find snow boots that look almost exactly like regular leather/sued boots except they’re waterproof or ones so extreme they look like snowboarding boots. Personally, I like Sorels the best because they’re hilariously over the top in terms of “Looking Like Your Dad” but they also come in funky colors.

I have one pair that are black and go up to my knee where they get so furry my dog barks at them and another pair that are ankle height and plaid. That’s right, I have two different pairs of the same brand of snow boots. I live in New England and these are things I need.As far as I’m concerned, winter boots should always be worn outside your pants. Even if you’re not into skinny jeans or wear particularly baggy pants, winter boots go on top. Otherwise your pants will get wet and salty like the tears you will be crying from how much colder this will make you. Yes, there are winter boots that look just like hiking boots but are winterized, but I don’t think those keep you warm enough.

Higher boots in black or a pattern will look more girly, a lower boot in brown will look more butch, and big chunky classic snow boots are super versatile with respect to gender presentation.


When to wear: To and from the place you’re going whenever it’s snowy/wet outside
When not to wear: Inside or at a party where you’ll get sweaty
What to wear them with: Anything! You’re adventuring outside in to the blizzard, but remember the boots always go on top! Try with wool tights and a dress, heavy snow gear and baggy jeans or with a ski vest, plaid shirt and skinny jeans.


Military Boots


This year military inspired boots are back with a vengeance, which is great since they might just be the best queer boot on the planet. Actually, the boots that are in style are more similar to a traditional “paddock boot” for English horseback riding mixed with your classic combat boot BUT with a thinner sole.

Basically I’m talking about any boot with a flat, or near flat, sole that laces up about 7-10 inches hitting you above the ankle. Your military boot is your everyday, going to the bars, going to work, going to class, going grocery shopping, “taking your dog out” boot.

As long as you’re not sporting a super thick/rugged sole, you can wear military boots just about anywhere besides a semi-formal (or nicer) party.  The toned down, pointed toed, stylized military boots that are being shown right now could replace probably half of the other shoes you have.

Military boots usually come in your basic black, brown and grey, but I’m a classic kind of girl and like them best in black. Most of the styles being shown right now have a zipper down the side or back which is awesome because 1. It looks badass and 2. You never have to re-lace them up. It’s also easy to find military boots with a variety of heels. If you like a completely flat boot, they’re definitely available, however, if completely flat boots give you that duck-feet feeling so luckily you can find military style boots with heels. You can, of course, always switch out for the classic lesbian Doc Martin. There are three basic ways to wear military boots:

First, you can lace them all the way up and be done with it. This style works over very skinny jeans or under basically any other type of pants. You can also wear your boots like this with tightish pants rolled up to just above the boot.

Second, you can lace them halfway up and tie the laces at the ankles. The half-way lace is best suited for tucked in skinny jeans, straight leg pants or rolled up slightly and pinned flat flares.

Finally, you can lace work boots halfway up and fold over the top. Anita Dolce Vita, Features Editor at dapperQ, pointed out to me that this looks particularly cool if you boots have a colorful or interesting lining.

Another great way to wear military boots is with a dress. It takes the feminine edge off of wearing a dress in a distinctly queer way. I like wearing my black one with floral or overly girlie dresses and skirts to give them an edgy look. You can wear them with low socks so your bare leg just melts right in to the boot or scrunch down a ski sock so it just shows above the lip of the boot. A thick wool tight is also a cute option with a dress or shorts in the winter giving you a ski-bunny appearance.


When to wear: Everyday for your normal stuff or out to a relaxed bar
When not to wear: When going to dressier clubs or anything semi-formal or nicer
What to wear them with: Skinny jeans or straight jeans tucked in, looser jeans on the outside, shorts or to give girlier dresses an edgy look.


Equestrian Boots


If you want to look like Spencer from Pretty Little Liars and/or anyone with a ton of money, the best way to do so is by investing in a pair of riding boots. Riding boots are preppy in the best way possible. Dont’ get actual riding boots, of course, those are expensive and scary, but you can find riding inspired boots anywhere. Your riding boot should come up anywhere from mid-calf to just under the knee and be leather or faux-leather with a flat sole.

Some riding boots, called “field boots,” have laces up the ankles but not all the way up the leg. Traditionally this is meant to support your ankle while riding, non-traditionally this is meant to look awesome/dapper.

Others resemble a more run-of-the-nill black leather boot, which support a harness at the ankle or a strap/buckle at the top. Many riding boots  have a distinct cuff at the top which is distinguished by color, texture or even just a seam.

However, riding boots traditionally lack a zipper, which means you’ll often find yourself having to jam your sweaty foot down a boot unless you find one with an elastic panel (which gives your calves some breathing room). But side and back zippers are popping up more often on riding boots these days, hidden on the inner calf or along a seam or sometimes purely visible in a pop of color.

Riding boots provide a more “femme” silhouette while not being totally girly, and therefore they perfectly complement a femme preppy look, such as skinny pants + blazer and/or loose blouse. But riding boots are actually quite versatile — ’cause they lack a high heel, you can wear them to work or other business-casual type settings or throw them on with short dresses or skirts during the day. However, when paired with skirts that go past the knee, riding boots can give you an ‘overly bundled prairie style’ look’ and riding boots also look weird underneath jeans. Riding boots are designed to be worn over riding pants, after all, and the slim foot and lack-of-heel makes them a flop underneath a straight or bootcut leg.

Plus, riding boots can be very expensive, so why hide them! (I also love how riding boots look with a bit of knee high socks sticking out the top!)


When to wear: For work, dinner with friends or anytime you want to look particularly preppy. Particularly cute with a blazer. Or horseback riding.
When not to wear: When going a semi-formal event or anyplace they might get trashed
What to wear them with: Skinny jeans, straight jeans or flares tucked in, short skirts or shorts with tights but rarely with longer skirts.
Next: More boots and team member’s top picks!

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Lizz is a consumer, lover and writer of all things pop culture and the Fashion/Style Editor at 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 261 articles for us.


      • The Steve Madden (?) boot that folds over and has the zipper on the back…they call it a “combat” boot…it looks exactly like my paddock boots…right down to the arena dust lol.

        • I have that boot in gray w/ blue zipper!! I love it, I wear it everyday.

          I feel like military and equestrian style overlap because if you look at it historically speaking, military soldiers use to ride horses, right? …. soooo yeah, there’s gotta be some conflation of the categories.

          • I think actually, while you’re definitely right about “military” or “combat” boots looking more utilitarian and more like something you’d wear in a horse paddock, the “equestrian” boot or “riding” boot is specifically designed for RIDING the horse, not just taking care of them. They’re tall to protect your legs from the saddle, etc (read more here,

      • Oh gosh, don’t cry! This is a well-researched and entertaining and provocative and beautifully crafted article! Fashion is overwhelming and confusing and there you are, marching out into the world and trying to make some sense of it for us, with sexy photos and two whole pages of entertainment and everything.

        MAD RESPECT!

  1. Boots are kind of my thing..I worked in a shoe store all through college..Employee discount helped solidify my footwear obsession..I have 2 shoe closets..It’s a sickness and I don’t care if there’s a cure..I love me some boots!

  2. i need to print this out and save it forever. i’ve lived in chicago for three years and still feel like i don’t know what to do with boots. they’re so pretty but i haven’t bought any beyond the purely functional snow boots. this is because in my hometown of miami, the most popular boot-look is the uggs with a short skirt thing when it drops to 50 degrees outside.

    anyway. very helpful. thank you!

  3. Beautiful article. Just when I was shopping for a new pair of boots too! My favorite pair of cowboy boots are actually ankle high, which helps make them more appropriate for city settings I think, but I find it so funny to see all these English girls walking around in very western cowboy boots. Not even in the right country!

    • And they back it with a 100% satisfaction guarantee..I recently called to order new “Duck Boots” because my 10 year old pair had worn through the rubber sole..The Customer Service rep urged me to send them back instead..And L.L. Bean sent me a friggin new pair! I love Bean..Bean is the Bomb!

  4. it’s a little late in the season for winter boots where I am since it’s starting to warm up and we’re really heading into march now, but I have to say I have a weakness for over the knee boots (though I think they need to be worn with a specific look), and I also own too many pairs of cowboy boots.

    All the boots!

  5. Sorel Tivoli plaid boots? Yes, I own them. And I also own a pair of red ones. I’m addicted to Sorel snow boots.

    I also own riding boots, the real, evil kind that will leave sores on the backs of your knees and blisters all over your feet. But they look gorgeous. And they’re not made for walking anywhere, ever. I’d have sex in them though. You don’t have to walk during sex, mostly. Just sayin’


    Also the category of military boots was sorely lacking in combat boots? For which Doc Martens are the classic solution. I personally have a pair of John Fluevog Angel Derby Swirls, which are like DMs but better, I’m convinced. Really anything that Fluevog sells is pure magic.

    I also recently obtained a pair of black equestrian boots by an Austrian company called Gabor, and they’re amazing. Not sure if they’re available stateside, but they make a fantastic boot :)

    • That lack of combat boots was sort of somewhat intentional. I don’t personally find the thick sole kind of combat boot to be as versatile as the flatter sole style military boot. That doesn’t mean you can’t still wear doc martins and love them forever.

  7. Alright, guys. Are more expensive boots really worth it? I go to school on a huge campus and walk about 2 miles a day just going to class. Coupled with New England weather changes this has led me to ruin THREE pairs of rain boots and 2 pairs of regular boots in five semesters.

  8. Just because a boot is expensive, doesn’t mean it’s well made..Materials play a huge factor..So does manufacturing (as I stated earlier..I sold shoes for 4 years) Man-made vs leather vs fabric..How about the sole..Material? Thickness? Is it layered and if so..How are the layers formed? Also, also, also..If you look at that pic of of Toe shapes, You will see single stitch vs double stitch..These are all things to consider when buying a boot/shoe for lasting use and comfort..

  9. I didn’t realise how many pairs of boots I owned until I read this article.

    My favourite are a riding/equestrian pair, similar to the awesome ones Molly Ringwald wore in The Breakfast Club but better, if that’s possible, as I’m not gonna lie – hers were pretty pimpin’.

  10. BOOTS ARE MY FAVORITE FASHION THING EVER. I think I wear boots at least 6 days of the week, regardless of the season. I have six pairs and can never get them to last more than a year, I wear out the soles so much.

    I desperately need cowboy boots, though. And military boots. And over-the-knee boots. I clearly need to go shopping.

    Also, I have Coach snow boots, and while they actually have zero insulation, need 2 pairs of thermal socks underneath, and don’t really work in over 4 inches of snow, they’re ADORABLE. So yea.

    Re: Ugg-like things. I have some and they’re pretty much the most comfortable thing ever. All of my other boots are nice and pretty, and dammit if I want to wear leggings and comfy boots with a long sweater one day, then I’m going to. Judge me all you want, I’m just warm.

    I really <3 boots.

  11. You know what goes great with boots? Cats.

    YOU GUYS, I cannot recommend these Merrell boots enough:

    I came into a pair (in brown) last fall and they are 1) incredibly comfortable, 2) totally waterproof – seriously I wore them on assignment in pouring rain for two days and my feet were completely dry, and 3) reasonably warm without being too hot.

    They have changed my life I love them so hard.

  12. I met my best friend (also gay) when I was in college. I tend to come off so femme most people never realize I’m mega gay, so after a hanging out a bit I figured I should give him the memo. He laughed and said he knew before we ever met, of course I asked how and he replied, “I noticed you walking across campus in those combats boots…only a dyke could rock those!” Lmao.

    Boots for the win!

  13. i love the leather/wingtip hipster-style boots that are all over Forever 21 and H&M like nobody’s business. i must have atleast 1 pair in my closet at all times.

    there is nothing like wearing a pair of those/converses after theyve been broken in. SO COMFORTABLE, FOOT HUGS ZOMG.

  14. I wear my combat boots as my dress shoes…and no one knows the difference. Its gone through semi-formal, job interviews, internship, work…and costuming related stuff. I do keep them in pretty good shape and polished… so that might be why no one can tell lol

    Now i want to go and buy a pair of knee high boots since i just returned a pair which didn’t fit me like i thought it would…

  15. Oh, Lizz, you have no idea how much joy this post fills me with. It’s like porn for boot lovers. Thanks especially for the diagrams about the different parts and toes of a boot, now I can express exactly what I’m looking for :)


    Ummmm how in god’s name could you forget motorcycle boots, when pretty much every girl with whom I’ve clam jammed was wearing Fryes when I gave her a dyke-nod from across the room, and subsequently approached her, saying, “Hey, may I buy you a drink?”

    I’m borderline offended that you failed to include these.

    And Blundstones or R.M. Williams’ depending on which continent you’re Nancy Sinatra-ing.

    Totally bumming that you didn’t devote entire categories to the aforementioned dykifiers.

  17. I like some boots, but it’s hard to find ones that I like that fit. I have ridiculously small ankles so generally they’re massive around the ankle and my foot comes half way out when I try to take a step.

  18. I love boots! Thank you for this, it’s a fantastic reference. I have a lovely pair of snow boots that work for semi-formal events/being inside, actually – they are furry on the inside, and they roll down, to just above the ankle, so it’s this very classy fur boot thing going on (fake fur!), but not terribly warm. And as soon as you step outside, you can roll up the “shaft” and be warm again.

    I also have to disagree with you a little re: equestrian boots with longer skirts. I have a lovely pair of equestrian boots (these, actually: that I adore pairing with a heather grey knee-length A-line skirt, especially with a patterned tight underneath. Very classy, femme, understated.

  19. I just feel like the Americans ruined the uggboot for us Australians. They were never meant to be an outside boot! They are strictly to be worn inside preferably while wearing trackies, pjs or a dressing gown.

  20. i have doc martens chukkas and they are beyond awesome. additionally they required no wearing in period and were instantaneously comfortable, unlike the regular 8 hole docs which i also find just have too much ankle space. though, those are classics for a reason (sweet, sweet silhouette)

  21. Aw, my favorite boot style isn’t listed here (“Granny boots”! – victorian-esque midcalf lace-ups with a thick medium heel)… Does that mean my boots aren’t queer enough? ;)

  22. This article is so helpful and related to my interests~

    however, I still have two questions:
    -Is there some kind of boot that is appropriate in more formal settings?(except cowboy boots in the south)
    -What about motocycle boot? Do you have to tuck your pants into them?

  23. Now I’m sad because I want a pair of military boots in brown and I’ll never be able to find one because my feet are awfully small. (35 eu apparently 4 and half in american shoes system).
    Life is very hard for undersized feet people.

  24. Oh how I love boots! I recently dedicated one of my long rambling Tumblr blog posts to that very topic. Although it was more about boots in Paris but whatever. This article is just making me want to buy all the kinds I do not own!

    • Man, the U.K. is really the only place that seems to manufacture decent, high-quality vegan boots. Wonder why? My first pair were the vegan Gripfast steel-toed grinders, which I have searched the internet for in vain ever since they stopped making them. Recently got these guys — — from Vegetarian Shoes, which are nearly as good — a little more stylish, if possibly a little less hardcore, and required no breaking in. Fully recommended.

      • Vegetarian Shoes rocks my world. I discovered the Veggie Trekker Mk 4 on their website (for when I want to clomp around in the snow and feel like a badass), and then was able to order them in the US via Vegan Essentials.

        That Vintage Boot is pretty fantastic.

  25. yay for riding boots and over the knee boots, my favorite kind of shoes. i wear otk boots with short skirts and dresses (with tights) all the time. my belief is as long as it’s a flat over the knee boot, you don’t look so hoochified if you pair a short skirt or dress with it during the daytime. they balance each other out and you’re pretty covered. all you’re showing is upper thigh. i would never wear a high heeled over the knee boot unless i was going to the club or unless i was wearing it with pants or leggings. and i used to go to school in upstate new york where it snowed non stop every 10 seconds and i got a pair of hunter rain boots and wore them in the snow and rain. they’re waterproof either way, and i wore them with boot socks in the snow for warthm.

  26. YAY FINALLY A PICTURE OF THE BEATLES IN THIS PLACE. As someone who continues to be strongly influenced by the Beatles in my fashion choices, I am very pleased to see them representing Chelsea boots. Although, I’ve been trying to find a satisfactory pair forever, and I haven’t found them yet. I might be too picky. BUT BOOTS ARE JUST SO EXPENSIVE. And I know that’s obvious, but ugh.

    This was a very enlightening article though. Especially seeing as I found Autostraddle because I was looking for a place that talked about fashion from a non-heteronormative perspective. xD YAY MORE FASHION ARTICLES! <3

  27. This is like the damn jackpot for a girl who had only worn Chuck Taylors and Adidas indoor soccer sneaks and then had to buy boots when she moved to DC. The cheap rookie ones I got are already tearing apart. A new purchase will be made asap.


    Can anyone recommend me a good brand for long-lasting, authentic ones? I know of Frye but they are hella $$$$ and probably not too authentic. I should have picked up a pair of good cowboy boots when I lived down south haha

    • I have some Frye boots and if they’re not too far out of your price range I do recommend them. They’re super comfy and have lasted me more than a year so far of pretty constant usage. I think Ariat boots are a bit cheaper although maybe not by much. You could go to or bootbarn and do some investigating?

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