Over the last year, we’ve gotten tons of reader questions about the state of our skinny-jean-wearing nation. It’s been under attack from Gen Z, leaving many of us 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.

**psst! This post was originally published last March, but was just updated with all new boot selects for Winter 2022.

The Top 8 Pairs Of Boots To Wear With Straight-Leg Jeans

After hours of trial and error, we landed on straight-leg jeans as being the easiest non-skinny jean to style — especially in cold and wet weather. We quickly ruled out flare jeans in winter (they’ll drag on the snowy, muddy ground) and mom jeans (with their signature tapered leg.) Mom jeans, we found, are especially awkward with warm winter boots. Straight-leg jeans, however? 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

Similar Jacket | Jeans | Leggings | Boots | Hat | Similar Mittens

Whether you call them Bean boots or duck boots, 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 jeans 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 (similar can be found at Backcountry), 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 leggings under the jeans for extra warmth, too.

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2. Wedge Sorel Boots

Similar Jacket | Similar Tee | Similar Jeans | Similar 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 rains, too.

Outfit details: Wearing an XS in the Lolë jacket, (similar one at Backcountry), the Anine Bing tee is a size small, and the rag & bone Maya jeans a size 26.

Similar Jeans | Similar Sweater | Coat (Similar Color) | 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 boots (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.

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3. Winter Hiking Boots

Sweater | Similar 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 wool socks to 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 (find similar here).

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4. Shearling-Lined Clog Boots

Similar 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 Saks, too.

Coat | Jeans | Boots | Similar Cashmere Gloves 

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 Platform Chelsea Boots (High Shaft)

Jacket (exact color sold out) | Jeans | Boots

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).

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6. Chunky Chelsea Boots (With Socks)

Coat | Similar Turtleneck Sweatshirt | Jeans | Boots | Similar 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.

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7. Doc Martens

Jacket | Similar Sweater | Jeans | Boots

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).

Jacket | Similar Sweater | Jeans | Boots | 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 Shopbop, Amazon and Anthro.

8. Danner Hiking Boots

Jacket (exact color sold out) | Jeans | Boots | Similar 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.

Jacket (exact color sold out) | Jeans | Boots | Similar Bag | Hat | Mittens

Outfit details: My Patagonia puffer is an XS, the rag & bone jeans I’m wearing are a size 26 (exact style is Maya), and the Clare V bag I linked isn’t my exact one, but it’s really close (and almost 50% off). 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