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


Rain Boots


I don’t have a ton to say about rain boots. Rain boots err on the side of girly but in black can be pretty androgynous, especially if you pair them with sort of a solemn “It’s Raining in Paris” black trench coat.

Now when I was 17 I shamelessly acquired this overly expensive pair of Burberry boots but I still rock that shit every time there’s a drizzle. They’re the best rainboots on the planet: they’ve yet to spring a leak and the back-zipper saves me from foot-stuffing catastrophes. That zipper is a complete game changer.

Much like snow boots, rain boots are sometimes-shoes so you can get away with more and the many colors/designs provide for fun mixing-it-up times when it’s yucky outside. Remember to tuck in your pants, obviously, lest your pant leg become wet & dirty.


When to wear: When it’s rainy outside
When not to wear: When it’s not rainy
What to wear them with: Basically anything, as long as you’re okay with looking somewhat femme or sporty.


Over the Knee Boots

Over-the-knee boots are in the category of “shoe too cool for me to wear.” Previously only visible in go-go costumes or dominatrix outfits, these boots have been making a comeback in everyday style. The latest over-the-knees are like the lovechild of riding boots and go-go-boots and manage to cover your knee in front but not surpass the crease of the back of your knee, thus making them one hundred billion times more comfortable than thigh-high predecessors.

While over-the-knee boots are a truly femme style, super-platform high heels and patent leather will look too costumey. Go for a suede of distressed leather in a light to medium brown with a narrow foot and a flat sole. That way it’s almost like you’re just wearing the most badass riding boots ever.

Over the knee boots can definitely bring up What The Hell Do I Wear With That feelings. A totally safe bet are leggings with a longer blouse/button up. Beware of skirts or dresses with over the knee boots, it can look very costumey/dated.

I think over-the-knees look awesome with short-shorts and tights, but my roommate says it looks trashy. Decide for yourself.


When to wear: In casual settings.
When not to wear: Anytime you need to look dressed up/appropriate.
What to wear them with: Leggings and maybe shorts with tights depending on how adventurous you are. Skip skirts on this one.


Ankle Boots

At the bottom of every boot is an ankle boot, so this is one big fat category. Generally speaking, I think of ankle boots as encompassing three subtypes of boots: booties, Chelsea boots and chukkas.

1. Booties

As you can probably tell from the “ies” ending, booties are the most femme of the three types. These lace-up or zio-up high-heeled boots cut somewhat at the ankle, come in all sorts of styles and colors (I love an oxford pattern), and even look cute as peep-toes or wedges.

Dressier, higher-heeled booties work as a formal attire show and complement an above-the-knee OR full skirt or dress. My favorite aspect of high-heeled booties is that you can wear them with a cornucopia of nicer women’s pants while avoiding the “tuck or not to tuck” dilemma and providing greater accessibility to women with different body types.

Leggings and skinny jeans look great with booties, but wide-leg, boot-cut and straight leg slacks look AWESOME with booties.

Lower-heeled booties can make great casual shoes, look sexy for going out in skinny jeans/leggings and look great with shorts. If your bootie is more sturdy and casual, you can wear it with socks and look adorable and probably could even pull off a cool look with cargo pants.

Though booties are generally a pretty femme trend, you can create a great androgynous gender-bendy look by mixing them with menswear. Imagine how cool black stiletto peeptoe booties might look with a white button-up, suspenders, black pants and slicked back hair!


2. Chelsea Boots

“Chelsea boots” are like an English riding boot that gave up halfway through: low heeled and tightly fitted, these babies end narrowly at the ankle and sport the Chelsea boot signature of an elastic band on one or both sides. They look great with most cuts of pants and are basically gender-free in terms of styling, which’s great if you want an androgynous work shoe.

Chelsea boots were originally designed as riding boots during the Victorian era but were repopularized in the 60s by the Beatles and then again in the 70s and 80s by their appearance in Star Wars.

There’s a 90% chance your mom has a pair of these. My mom swears they’re super comfortable so they’re great if you work on your feet all day.


3. Chukkas

Finally I come to chukkas. You might not think you know what a chukka is, but I bet you actually do. They’re those suede hipster ankle boots with only two laces eyelet. What I love about chukkas is that they’re, like Chelsea boots, gender-neutral but, like booties, look awesome with everything.

Because they only lace up a little bit, chukkas walk the line between flats, loafers and ankle boots. You can just as easily wear a pair of black chukkas with a pair of patterned tights and a cute dress as you can a tan pair with straight leg slacks, a button-up and a bow tie. Two equally awesome looks, one type of boot.

They are similarly easy to dress up and dress down.

There’s one rule about chukkas — actually, it’s bout all ankle boots: they just don’t look good with cropped pants. That two-inch band of skin above your ankles between your pants and boots is mega unflattering.


When to wear: In a casual or semi-formal setting depending on the boot.
When not to wear: In an ultra formal setting
What to wear them with: Anything except cropped pants. No skirts/dresses with Chelsea boots either.


Comfort Boots


Some of the most amazing types of boots weren’t necessarily designed for a trip to the club. This category includes sweater boots, Uggs and Ugg-style boots

I’m not hating on Uggs. There’s nothing, and I mean nothing, as satisfying as slipping into some warm soft shearling (or faux shearling) boots first thing in the morning to grab a bagel and walk your dog. They’re like a wonderful hug for your legs.

Similarly, a pair of super soft sweater boots are practically just upgraded socks. If I had a fireplace I would wear sweater boots in front of it every day. Everyday.

However, and this is a big however, I just don’t think boots that are designed for snuggling are appropriate for work, social events or really anywhere you need to look remotely nice. Please withhold your pitchforks and burning. It’s not that there’s anything wrong with being comfortable, but between the hardline top edge and the duck foot; Uggs just don’t create a remotely flattering look.


When to wear: At home or while walking to yoga
When not to wear: In any remotely nice setting
What to wear them with: Leggings and your favorite sweatshirt


Cowboy Boots


Cowboy boots confuse the hell out of me, but I like them anyway. You see, I was a kid in the eighties and early nineties so I had a pretty sweet pair of white ones when I was three. Since that time, I’ve been living in New England where cowboy boots weren’t a big thing until recently. Now, slowly but surely, it’s starting to look like a rodeo around here.

Due to their ever-increasing popularity, it’s increasingly easy to find pairs in a range of styles/colors, which is great for those with large or small feet. Cowboy boots are also super-sexy on a masculine-of-center girl and offer a way to get a little extra height without looking too girly. The key is subtlety.

Unless you’re actually attending the Pendleton Round-Up, you don’t necessarily want a super flashy boot that will lead you to be known around the neighborhood as “That Girl With the Cowboy Boots.” I like boots with just a little stitching and minimal inlayed color. Additionally, a more distressed leather makes a better boot for casual settings.

An eye towards subtly when wearing cowboy boots should extend to the rest of your outfit also. In order to avoid looking costumey, steer clear of plaids, tucked in button ups, Canadian tuxedos (jeans with denim shirts and a jean jacket) and peasant blouses. These all add to the cowboy costume effect.

Casual cowboy boots are great with shorts, knee length or above skirts or with jeans. If you’re looking for more of a statement or femme look, tuck your jeans in to your boots. Conversely a more subdued or butch style is to wear bootcut or straight leg jeans on the outside of the boots. There is, as with everything, a gradient in between, particularly if you’re actually in the South where men sometimes wear knee length cowboy boots (buckaroos) outside of their jeans. Jeans worn on the outside of cowboy boots should be long enough that they fold over/scrunch a bit in the front, but not so long that they drag in the back.

But if you’re a Southern or Midwestern dweller with masculine-of-center leanings, cowboy boots have a whole other non-denim world to explore. Dressy cowboy boots (which can easily surpass $400) work underneath slacks in lieu of loafers, oxfords or derby shoes. Dress cowboy boots can even be worn with a tux to some southern black tie events (usually the invite with specify Wester Black Tie). Keep in mind, however, that this is limited to high quality polished leather or snakeskin boots.

One last thing to be careful of when buying cowboy boots. Make sure they properly fit in the toes. I bought a beautiful pair about four years ago. Unfortunately I quickly discovered that if I tried to open a door the toes were so long that the door bounced back at me. If you have more questions regarding the fit and wear of cowboy boots I suggest checking out’s guide to cowboy boots.


When to wear: When it’s dry outside. For casual fun or clubbing in the North, also for work and formal events (with suits only) in the South and Midwest
When not to wear: To formal events in the North
What to wear them with: Pants, short, suits or flowy dresses. Avoid getting to cowboyed up with tucked in plaid button-ups.


Vegan Boots


Many people chose not to wear leather or other animal skins for a variety of reasons. This can be tough with boots. Obviously rain boots and snow boots come vegan-standard, but it can be really tricky to find good quality faux leather boots, especially if you’re also looking to avoid unfair labor practices and thus forego cheap-faux-leather shoes from mass-production stores.

Your local show store might not have very many good quality vegan boot options, so I suggest hitting the internet. Plenty of online shops, such as Novacas and Moo Shoes, sell exclusively vegan shoes. Alternatively, you can also just select “faux leather” on many mainstream shoe shopping websites, such as Zappos. Whatever your choice, remember two things:

First, because no natural leather is involved, finding vegan boots should actually be cheaper. Second, because no natural leather is involved, you may have to shop around more or even pay more (contradictory, I know) in order to find a high quality vegan boot.


Team Picks

Given the option to pick a boot, this is what our amazing staff and affiliates came up with:

Lizz: Sorel Tivoli Boots and OTBT Hutchinson Boots

Jamie: Loretta Vegan Ankle Boots from Novacas

Brittani: TBL 6-Inch Waterproof Flat Wedge and Men’s 6-Inch Basic Waterproof Boot
(“I got mine in high school and they were both like special editions so they’re a little different and thus cooler but whatevs.”)

Anita Dolce Vita, DapperQ Features Editor: Steve Madden Cablee Boots and Sperry Top-Sider Starpoint

Laneia: Frye Harness 15R

Carmen: Laredos

Rachel: Dr. Martens Castel 8-Eye Boot

Laura: Clarks Saloon Dillon

Sara Medd: All Saints Vintage Damisi Boot

Well there you have it, a nowhere near complete guide to getting your queer boots on. Whether you just can’t live without your wellies or you’re finally figuring out how to style cowboy boots, there’s no better time to catch boot fever than in the middle of the winter heading in to spring. So everyone share your boot stories!

All images from unless otherwise specified

Pages: 1 2 See entire article on one page

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 276 articles for us.


  1. I gotta say, the second set of “military boots” look more like paddock boots (“equestrian” boots) than do the “equestrian boots.”

    But I also don’t know too much about non-horse-related fashion, so.

      • 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.

      • 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!

  2. 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!

  3. 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!

  4. 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!

  5. 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!

  6. 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.

  8. 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.

  9. 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..

  10. 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’.

  11. 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.

  12. 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.

  13. 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!

  14. 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.

  15. 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…

  16. 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.

    • Those brands don’t really have any currency outside the land down under though do they?

      I can’t justify the expense of R.M. Williams ($300 for ‘work’ boots?!?), but I do like me some Blunstones. They’re great for when you want something sturdy that isn’t hiking boots.

  18. 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.

  19. 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.

  20. 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.

  21. 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)

  22. 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? 😉

  23. 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?

  24. 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.

  25. 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.

  26. 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.

  27. 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

  28. 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?

  30. Pingback: Ariat Womens Caryn Shirt

  31. CARMEN!!! I have your boots!! No seriously, though. I have those exact style of boots. Down to the lace hooks and fringe. I got them at the Goodwill.

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