If there’s ever a season where skinny jeans really shine…WINTER. I know articles pop up from time-to-time, warning us all that skinny jeans are about to be “Over!” or encouraging us all to replace our skinny jeans with mom jeans/straight leg jeans/whatever…but then winter comes and the anti-skinny hysteria dies riiiiight down. Why?
‘Cause skinny jeans were made to be worn with boots.
Which is probably why we get so many reader questions on the topic of wearing skinny jeans and boots. What are the best boots to wear with skinny jeans? We want some fresh ideas, yet our lifestyle requires both practicality and longevity.
So. Keeping in mind a few Real Life Limitations, as well as taking current trends into gentle consideration (we don’t live and die by trends, but they’re worthwhile to consider) here’s our short list of the best boots to wear with skinny jeans…now.
The Best Boots To Wear With Skinny Jeans In Winter
- Best Boots Overall: Flat Over-the-Knee Boots
- Best Boots For All-Day Walking: Sneaker Boots
- Best Boots For Work: Sock Boots
- Best Boots For Serious Cold: Snow Boots
- Best Boots For Slushy Days: Waterproof Hiking Boots
- Best Boots For Just Running Out Quickly: Mini UGGs
- Best Boots to Beat Winter Blahs: Taupe Mid-Shaft Heeled Boots
- Best Boots to Pair with All Jean Styles: Western Boots
- Best Boots to Add Some Edge: Doc Martens
1. Best Overall Boots: Flat Over-the-Knee Boots
Why did flat, over-the-knee boots get our top nod? Because they hit all of our major criteria. They’re classic, yet enough of a statement boot to instantly elevate any outfit — the vibe of over-the-knee boots is decidedly chic. And when the pair in question also has a flat, walkable sole? They quickly move into practical territory, too, for being both very walkable and warm. I’ve been wearing my Stuart Weitzman Lowland boots for years now, simply because they’re good on so many levels.
Favorite Pairs Of OTK Boots
2. Best Boots For All-Day Walking: Sneaker Boots
Sneaker boots are basically classic Chelsea boots, but with a sporty edge and a comfortable, walkable sole. Unlike regular sneakers, they’re easy to wear with thick socks, making them perfect for cold weather. Sneaker boots have a street-chic vibe that feels modern and fresh, yet they’re simple enough to be classics. Personally, I’ve been wearing my Vince sneaker boots for years now, and — as a sign that they’re not going anywhere — Vince just re-released them.
featured: Vince sneaker boots
In recent years, sneaker boots have become even more weatherized (holla, northern mamas) and are now even available in waterproof styles. Other iterations include furry linings, and/or soles with serious traction. (My Sorels, as an example, can stand in as snow boots — see them below, right.)
My Favorite Sneaker Boots (Including Weatherized Options)
3. Best Boots For Work: Sock Booties
Sock boots are basically just ankle boots with a higher, narrower shaft. The narrow shaft means that the boot slides easily under the leg of the skinny jean (instead of bunching or competing or requiring the jean to be cuffed). The resulting line is sleek, clean and modern.
If you have ankles that tend to be too thick for boots, or ankles that tend to be too scrawny for boots…sock boots with a fabric upper are the safest bet (like the Everlane ones, below).
featured: Everlane ReKnit Booties (made from recycled fabric!!)
4. Best Boots For Serious Cold: Snow Boots
There are just some…realities to winter, and for many parts of the world, serious snow boots are one of them. I’ve yet to meet a single snow boot that doesn’t work with skinny jeans. Mom jeans, on the other hand…oof.
featured: Sorel 1964 Boots
5. Best Boots For Slushy Days: Waterproof Hiking Boots
Hiking boots have been having a bit of a resurgence in the fashion world as of late…which is good news for us practical mamas. And while I probably won’t be pairing mine with a floaty dress any time soon, I really love my waterproof hikers with skinnies, especially when it’s cold and/or slushy outside. Wear with thick, cozy socks (it’s OK if they peek through).
featured: Danner Mountain Light Hiking Boots
6. Best Boots For Just Running Out Real Quick: UGG Classic Minis
I’m never not gonna recommend UGGs. They have so many uses, especially when it’s cold, and you just need to run out really quickly and mayyyyybe you don’t even want to bother with socks?
UGGs are my winter flip-flops. (Feel free to shame me about regular flip-flops in June. I will be just as impervious then, too.)
And if you’re going to go the UGG route, I’m still a huge fan of UGG minis. (Side note — I don’t recommend the black. Ironically, the black gets dirty wayyyy too easily.)
featured: UGG Classic Mini Boots in tan
7. Best Boots To Beat Winter Blahs: Mid-Shaft Heeled Boots, in Taupe or Tan
Tall boots over skinny jeans is such a polarizing topic, but a fresh twist on the same general theme is to swap ’em for a pair of mid-shaft heeled boots. These mid-shaft boots hit lower on the leg, and are often slouchy. Personally, I avoid black mid-shaft boots — taupe or tan is a fresher option, and they make my usual black accessories look more modern.
Bonus points: These boots are genius with dresses or skirts, and…they’re really good for the latest trend of stuffing wider leg pants into tall(er) boots. True story.
Lastly, to really liven up a late-winter/early-spring outfit (and by the time we’re here, I REALLY NEED something that feels like spring), try pairing taupe (or tan) midi boots with a light bag. Even if your — ahem — giant parka is the usual black, gray or olive…it all works.
8. Best Boots To Wear With All The Jean Styles: Western Chelsea Boots
Full disclosure: my favorite way to wear these western booties is with cropped straight-leg jeans (or mom jeans or boyfriend jeans — see ’em all here). But since most of us do value versatility over here at TME, I felt that it was important to mention that that these booties also work with our trusty skinnies as well. Unlike other ankle booties, I actually prefer my skinnies to come down over the top of boot. See pic below.
featured: Paige Willa Chelsea Boots
Favorite Western Booties
9. Best Boots To Add Some Edge: Doc Martens
I’m trying to remember a time in my life when Dr. Martens haven’t been a thing and I’m…coming up…short. They’re always a thing. Just like the Clash and the Sex Pistols, they will always be cool. And when my winter outfits (#allblack) start making me cry real tears of sheer boredom…I add a pair of Docs because badass will always trump boring.
ps. The soles are actually pretty darn perfect for icy streets, too.
featured: Dr. Marten Leona Boots
Favorite Combat Boots
How do you guys wear your skinny jeans in the cold weather? I’m a sneakers girl in the fall, but once it gets seriously cold…gimme some BOOTS. Tell us which are your favs!