Brrr It’s Cold Out There: It’s Time To Get You Some Boots

Feature image from Hudson

I’ll be the first to admit: I am a shoe fiend. My parents liked to call me Imelda Marcos, and I never seem to run out of occasions for a new pair of footwear. So, naturally, finding a new pair of cold weather boots is not a job I take lightly.

As far as winter footwear is concerned you have two choices: fashion or function. The two occasionally cross paths, but from my experience, a pair of boots will lean more to one direction. That doesn’t mean your choices are look cute and freeze or stay dry and sacrificing lookin’ winsome. Lovely human, you’ve got options.

boots are for walkin 14

photo from Avant Blargh

Heeled, flat, tall or ankle length, the co-parents of the modern boots came from a place of function and protection. In the beginning boots were made to protect the wearer from the elements, then eventually evolved into occupationally specific footwear (function)/fashion footwear (style). Luckily, these days most of us require both practicality alongside style, and companies are listening. With traditional working brands such as Dr. Martens & Frye holding a large portion of the market on durable but good-looking boots, there are many mid-range options/styles regardless of your climate/budget.

This is a shortlist for inexpensive to mid-range boots that aesthetically pleasing & durable. There are many, many more options than these, but it’s a good place to start.

But Lyd, now that I’ve got them… how do I wear my boots? Here’s a mini “how to wear ’em” encylopedia!

Chelsea Boots

boots are for walkin chelsea boots

photos from tumblr and

boots are for walkin 12

photo from Avant Blargh

A steadfast choice — classic, chic and timeless. They are super easy to style (they go with everything) and easy to put on.

Lace Up Boots

boots are for walkin 9

photo from Madewell Tumblr

boots are for walkin lace up boots

photos from Ari Fitz and DapperQ

I’m smitten with the look of lace up boots — a harkening to spending evenings at the skating rink in hockey skates. Although laces may be cumbersome or difficult to do up, there are many “laced” options with side zippers, which means these are much easier to get on than they look!

Knee or Tall Boot

boots are for walkin tall boots

photos from Clothes Horse and Kieko Lynn

Depending on how cold your climate is, these might just be necessity. But a sound option doesn’t have to be drab – have fun with hem lengths in tall boots.

Trend Conscious

boots are for walkin trend boots

photos from I Go By Frankie and Zero Style

Perhaps the most frivolous of the bunch, these are my personal favourite! Fun loving and hardly practical, these are less of an investment and more of an exercise in treatin’ yoself. Cut-outs, bright colors or interesting heels; anything eye-catching and/or innovative is the name of the game.

Tips and Tricks

Befriend a cobbler. Resole, polish, take care of your boots! If you treat them with love, they will love you right back.
Use non-aerosol weather resistant sprays, or if you are looking for non-chemical solution, beewax works as a protectant as well.

If you can save for a $100 pair versus $30, do it. You’ll end up replacing the $30 many times over, so keep cost per wear in mind with your selections. I have learned this lesson more times than I would like to admit…

Choose natural materials over synthetics! Wools, cottons and leathers wear better than PVC and other synthetics. You will get longer wear + more mileage from boots with made from natural materials. Not to mention leather ages so beautifully…

Each winter I fall in love — with a new (or old) pair of boots in my wardrobe.  I’d love to hear which boots get you through the blustery winter months!

For more boots, you can check our archives here and here.

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Lydia O

Lydia Okello is a feminist, body positive, queer personal style blogger. On her website Style is Style, she showcases her panache for bright colors and power clashing. When she isn't pawing over Samantha Pleet collections on Tumblr, she's dreaming about havin' a kitten of her own one day. You can find her on Twitter, Tumblr and on her personal blog.

Lydia has written 64 articles for us.


  1. I’d like to add that Doc Marten has excellent vegan leather boots! I’ve had my current pair for two years now (I got them on sale, too!) and they’ve served me very well. They’re sturdy and protect my delicate baby feet from all sorts of weather.

  2. Ahhhhhh thank you! Seriously this entire winter not a day has gone by where I haven’t thought “Hmmm, I need to get me some boots.” I’ve been wearing my beat-up off-brand converse with the backs torn out, but now I’ll have options.

  3. after the death of my dream boots a couple of years ago (vivienne westwood pirate boots, thank you very much student loan 2009, gone but not forgotten) i hadn’t seen any that i really loved until i was in italy last week and found the most perfect pair. they’re like chelsea boots but with a way more substantial and chunky sole. and they were on sale, it was a christmas miracle.

  4. Bean boots bean boots!

    Probably more on the side of ‘function’ than ‘fashion,’ although there IS a whole tumblr dedicated to girls in bean boots, so that’s a thing.

  5. This post comes at such a perfect time! I just was thinking about how I need new boots. The zipper on my black nine west boots broke and I’m not sure if it’s worth it to fix and my other nine west boots are hurting my feet. Why oh why are Frye boots so expensive? They are so gorgeous.

    Any recommendations for affordable but super comfortable (and cute) boots? My feet and back start aching pretty quickly if I’m on my feet or walking for just a little bit and I need boots that can withstand trekking around NYC.

    • I have these pared down Dr. Martens that are less chunky than the originals but still great and super comfortable. Also Clarks Desert Boots, but they have little support. I’d go with something in the high-top sneaker family for the greatest comfort:cost ratio.

    • (Sorry I didn’t actually know what tretorns were until I read this article and I got excited about Josie and the Pussycats)

  6. about natural materials though! My absolute favourite winter boots right now are my forest green chelsea boots, but they’re also made of suede which living in the damp pacific northwest I’m frightful for the look of them.

    Also in Vancouver even though it never gets that cold so many businesses are obsessed with over salting their sidewalks, which ends up splashing onto shoes and again ruining them.

  7. Can cobblers replace a broken zipper on a side-zip lace up boot? Also do you have any recommendations for boot brands that have wide calves?

    • Some but not all – I took a pair of boots with that problem to one place who said they couldn’t fix it, but suggested trying elsewhere which says to me that it’s not impossible to do.

  8. Llbean had the best snow sneakers–insulated and water resistant like boots but they look like hightop sneakers.

  9. Keen has some super cute boots! some lean more towatds functionality than fashion, but I have a pair of their boots that have some heat-preserving tech (they have a cute name for it but I can’t remember it) that has saved my lil queer toes through a number of Massachusetts winters.

  10. Love all of these! I found the best winter boots ever this year, Cougar Pillow Boots. They’re rated for like -20c (necessary in Canada) but I’ve worn them in -40 with thick socks and been toasty. Plus they look freaking sweet and are a steal at $200, AND have hiking-grade grip.
    (I swear I’m not affiliated with the company, just super excited about my boots after 3 winters in a row of wearing shitty Converse sneakers.)

  11. I would love a list of warm and waterproof vegan boots that cost less than $100! (Or, less than $200 if they’ve been proven to be very durable…) Does anyone know of any??

  12. Auto, I love ya, but you can’t say inexpensive and then 1 line down have the first boot on the first link be $250. The shock alone is enough to kill me. At least work me up to it with a $75 boot but don’t just start with $200+, that is not inexpensive.

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