8 Practical Boots To Wear With Straight-Leg Jeans In Winter (& Early Spring)

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Over the last few weeks, we’ve been flooded with questions from readers about the state of our skinny-jean-wearing nation. It’s been under attack from Gen Z and many of you are wondering how to adapt. Now, we’re not blind trend followers here — there’s a strong element of wear whatever the heck you want — but there’s something to be said for keeping an open mind, as well as gently modernizing your look.

Which is where straight-leg jeans come in.

The Top 8 Pairs Of Boots To Wear With Straight-Leg Jeans In Winter & Early Spring

After hours of trial & error, we’re finally circling in on straight-leg jeans as being the easiest non-skinny jean to style — especially in cold and wet weather. Flare jeans drag on the ground getting mucky and mom jeans (with their signature tapered leg) are especially awkward with warm boots, but straight-leg jeans? Well. They’re the big winner.

Straight leg jeans are comfortable (especially when worn a bit oversized or slouchy), and, as it turns out, can be styled with some seriously practical boots.

I don’t love straight-leg jeans with giant winter boots (see my first attempt at “research” with my Sorel Caribou boots here), so you won’t find any big boots listed below…but there are still plenty of options for keeping that outfit cute and those feet warm and dry.

1. Classic (Preppy) Leather All-Weather Duck Boots

Straight-leg jeans are the easiest non-skinny jean to style -- especially in cold + wet weather. Flare jeans drag on the ground & mom jeans are especially awkward w/ warm boots, but straight-leg jeans? Well. They're the big winner.

Jacket | JeansLeggings  | Boots | Hat | Similar Mittens

Whether you call them Bean boots or duck boots, the LL Bean’s classic leather all-weather boot was my inspiration for this one. This style of boot works really well with non-skinny jeans. The key is to have the bottom of the jean hit right at the top of the boot (or cuff the jeans to hit in the right spot).

And if you need really warm winter boots (and yes, yes I do), I’m actually wearing UGG’s Airondack boots. They have that preppy L.L. Bean boot styling, are fully waterproof, but are also lined in sherpa (even throughout the footbed) and rated to -32C.

Outfit details: I’m wearing an XS in the Lolë jacket, which can also be found at Nordstrom Rack, and a size 26 in the MOTHER Tomcat jeans (a team fav). You can’t see it, but I’ve layered this pair of Zella cozy leggings under the jeans for extra warmth, too.


2. Wedge Sorel Boots

Straight-leg jeans are the easiest non-skinny jean to style -- especially in cold + wet weather. Flare jeans drag on the ground & mom jeans are especially awkward w/ warm boots, but straight-leg jeans? Well. They're the big winner.

Jacket | Similar Tee | Jeans | Boots | Bag

We’ve been longtime fans of Sorel’s lace-up wedge boots. They add a bit of height, are shockingly warm, and are as comfortable to walk in as sneakers. And if you stick to the non-shearling lined version, they’re actually pretty perfect for spring’s rains, too.

Outfit details: Wearing an XS in the Lolë jacket, which can also be found at Nordstrom Rack, the Anine Bing tee is a size small, and the rag & bone Maya jeans a size 26 (they’re on sale, too).

Straight-leg jeans are the easiest non-skinny jean to style -- especially in cold + wet weather. Flare jeans drag on the ground & mom jeans are especially awkward w/ warm boots, but straight-leg jeans? Well. They're the big winner.

JeansSweater | Coat Hat | Mittens | Boots

The key to wearing these boots with straight-leg jeans is that the jeans need to be long enough to hit at the top of the boot (or even a little bit longer). Keep things really warm with a pair of extra-long socks.

Outfit details: Scotti is wearing a size 28 in her MOTHER jeans, and a size small in both the Halogen cashmere sweater and coat.


3. Winter Hiking Boots

Straight-leg jeans are the easiest non-skinny jean to style -- especially in cold + wet weather. Flare jeans drag on the ground & mom jeans are especially awkward w/ warm boots, but straight-leg jeans? Well. They're the big winner.

Sweater | Jeans | Boots | Bag

There’s a category of lace-up winter boots that seem to hit the sweet spot between sporty and warm. We LOVE these types of boots, especially for spring’s mucky weather (but they also work pretty well in winter, too, as long as the snow isn’t horribly deep).

Happily, many of these wintery hiking boots are perfect with slouchy, straight-leg jeans. The key is to find a pair of nubby, textured socks that match the denim.

Outfit details: Wearing a size small in Jenni Kayne’s fisherman sweater and a size 26 in the rag & bone Maya jeans (which are on sale).


4. Shearling-Lined Clog Boots

Straight-leg jeans are the easiest non-skinny jean to style -- especially in cold + wet weather. Flare jeans drag on the ground & mom jeans are especially awkward w/ warm boots, but straight-leg jeans? Well. They're the big winner.

Sweater | Jeans | Socks 

Shockingly cozy, shearling-lined clog boots are a good example of under-the-radar cool, especially when paired with non-skinny jeans. These boots are a classic choice, but a cool, vintage classic you almost forgot existed.

Outfit details: Laura is wearing a size small sweater, and a size 28 in her MOTHER Tomcat jeans. Those jeans — a team fav — are also available at ShopbopAmazon and Anthro.

MOTHER Tomcat, No.6 Clog Boots, Levi's Jeans, that Amazon dress...these are a few of my favorite (fashion) things...My top 5 fashion finds I actually wear.

Coat | Similar Sweater |  Jeans | Boots | Cashmere Mittens 

Once again, the key is to have the straight-leg jeans hit (or cuff) at the top of the boot. And pair this combo with some sort of uber-cozy patterned sock.

Outfit details: Laura is wearing a size small in the infamous Amazon coat, and a size 28 in her MOTHER Tomcat jeans.

5. Chunky Chelsea Boots (High Shaft)

Straight-leg jeans are the easiest non-skinny jean to style -- especially in cold + wet weather. Flare jeans drag on the ground & mom jeans are especially awkward w/ warm boots, but straight-leg jeans? Well. They're the big winner.

JacketJeansBoots

The high-shaft chelsea boot is one of the few boot styles that can sneak up under the non-skinny jean, making it one of the sleekest options. While not as warm as the other boots previously mentioned, with some thick socks, this pairing is warm enough for most activities (although, on seriously cold days I still need my real winter boots).

Outfit details: I’m wearing an XS in that Abercrombie & Fitch faux-leather puffer, and a size 27 in the Levi’s 501 skinnies (size up — they run really small).


6. Chunky Chelsea Boots (With Socks)

Straight-leg jeans are the easiest non-skinny jean to style -- especially in cold + wet weather. Flare jeans drag on the ground & mom jeans are especially awkward w/ warm boots, but straight-leg jeans? Well. They're the big winner.

Coat | Turtleneck Sweatshirt | Jeans | Boots | Beanie

If you don’t go with a high-shaft chelsea boot…or if you’re tall enough that the top of your jeans are going to leave some leg showing, then bridge that gap with a pair of thick, cozy socks. The key here is to match your socks to your jean for the longest leg line.

Outfit details: Amy’s cozy coat is sold out in ivory…but there’s one size left at Nordstrom.


7. Doc Martens

Straight-leg jeans are the easiest non-skinny jean to style -- especially in cold + wet weather. Flare jeans drag on the ground & mom jeans are especially awkward w/ warm boots, but straight-leg jeans? Well. They're the big winner.

Jacket | Similar Sweater | JeansBoots

Doc Martens are another solid choice in the winter. Not only are they decently warm when worn with thick socks, but they can usually power through muck as well. And since they tend to a slightly higher shaft, they’re a natural pairing with non-skinny jeans.

Of course, if any leg shows, just add longer cozy socks (and we still love marled knit socks for pairing with denim).

Straight-leg jeans are the easiest non-skinny jean to style -- especially in cold + wet weather. Flare jeans drag on the ground & mom jeans are especially awkward w/ warm boots, but straight-leg jeans? Well. They're the big winner.

Jacket | Similar Sweater | JeansBoots | Socks

Outfit details: Laura’s Mountain Hardware Jacket is a size small, and her MOTHER Tomcat jeans are a size 28. They’re also available at ShopbopAmazon and Anthro.

8. Danner Hiking Boots

Straight-leg jeans are the easiest non-skinny jean to style -- especially in cold + wet weather. Flare jeans drag on the ground & mom jeans are especially awkward w/ warm boots, but straight-leg jeans? Well. They're the big winner.

Jacket | Jeans | Boots | Bag | Hat | Mittens

I’m finding that my Danner Hiking boots — or any sort of hiking boot with a similar vintage appeal — look surprisingly good with slouchy, straight-leg jeans! I personally prefer when the top of the jeans hit at the top of the boot (so taller folks might need to go for full-length jeans rather than cropped).

I’ve been wearing my Danner Hiking boots for YEARS. They’re basically one of my most-worn boots, and something I’ll likely have for many years to come. (If you want to see all of the reasons I’ve love my Danners, check out my article, Danner Boots: Are They Worth The Cost?). It might also be worth checking out Linzi’s recent article on finding cute hiking boots — the boots she features would work great, too.

And once again (at the risk of sounding like a broken record)…socks matter. I swear by these (in navy) or these.

Straight-leg jeans are the easiest non-skinny jean to style -- especially in cold + wet weather. Flare jeans drag on the ground & mom jeans are especially awkward w/ warm boots, but straight-leg jeans? Well. They're the big winner.

Jacket | Jeans | Boots | Bag | Hat | Mittens

Outfit details: My Patagonia puffer is an XS, the rag & bone jeans I’m wearing are a size 26 (style is Maya, and they’re on major sale), and the Clare V bag I linked isn’t my exact one, but it’s really close. Lastly, take 15% off the Danner boots with code THEMOMEDIT.

Did I miss any winter or rain boots that look good with straight-leg jeans? Would love to know what you guys are wearing….

xo,

S

5 COMMENTS

  1. The Joan Explorer boot – shows up under #3 – is a GREAT combo sneaker/boot for city living. They have a ton of cool colorways; I actually bought two pairs this winter in different colors. Great transitional shoe!

  2. Love you guys as always but would like to see more actual spring content that doesn’t involve boot posts 😬 maybe a spring trends post?! Dresses? White sneakers, etc.

  3. Sounds like Jenny must not live in the northern part of the country if she doesn’t think this is a timely spring post. 😉

  4. This is great!!! thank you so much. Just ordered a ton of jeans and wondered what the heck to pair them with. I will say that I somewhat echo Jenny- would love to know how to wear these jeans when it is not slushy/muddy spring- but the kind of spring that is sunny and hinting at warmth. I am an eternal optimist that lives in the northeast and hopes those days are around the corner.

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