How To Wear a Sweater with Jeans and Look Great

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Don’t know about you but when we think of men’s fall clothing, one particular style comes directly to mind: The sweater. Whether you’re talking crewnecks, v-necks, cardigans, turtlenecks — even the odd mock-neck if you’re feeling particularly adventurous — sweaters are a layering staple, adding a one-two punch of style and warmth to whatever else you’re wearing. And we’re willing to bet that, more often than not, you’ll be wearing that sweater with jeans. (For what it’s worth, so will we.)

Contents

Jeans and Sweaters: Three Next-Level Looks
Shorten Your Sleeves
Lean Into Workwear
Go All In On Cotton

Jeans and sweaters make a classic combo for a reason: They’re both warm and tough, and will look damn good with a pair of boots — no matter what style you find yourself sporting the most. Not to mention the fact that styling them together tends to be pretty intuitive, so long as the jeans you choose are from a men’s clothing brand that knows what they’re doing. But that’s not to say that there aren’t ways to make it your own. Thankfully, you’ve got us to step in with a little inspiration on how to look like a million bucks by upgrading the way you wear jeans and a sweater.

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Jeans and Sweaters: Three Next-Level Looks

Fall has become synonymous with “sweater weather” at this point. So it’s pretty reasonable to expect you’ve got a few jeans-and-a-sweater outfits on deck for the season. But that’s always the last thing you want your outfit to be — expected. So switch things up. Try something new. You never know — you might just find your new go-to autumn uniform.

Shorten Your Sleeves

It’s natural to think of the sweater as a long-sleeved layer, but there’s no rule that makes that the only option. Switch things up by giving a short-sleeved sweater a shot for a ‘50s-inspired look that’s perfectly suited for warmer fall days. Just bring a jacket in case the temperature drops when the sun sets.

Club Monaco Short Sleeve Texture Crew Sweater

Made from cotton with clean and minimal styling, this short-sleeved Club Monaco number will transition from sunny days to brisk nights with the greatest of ease.

Alex Mill Corduroy Work Jacket

Short sleeves mean you need an outer layer to keep your core (and forearms) warm when the temperature drops. Think of this Alex Mill Work jacket as the grown-up version of a classic denim jacket: Just warm enough, and with a whole lot of style.

Madewell Slim Jeans in Gosbrook Wash

You can’t go wrong with light wash denim — it’s got all the classic style of great jeans, but it brings a modern twist to the whole thing. Just look at this Madewell pair and you’ll know what we mean.

Lean Into Workwear

Sweaters have a rich history, being worn by sailors and workmen alike. Next time you go to throw on a sweater and jeans, pay homage to that history by wearing styles that lean more heritage than modern. Like, say, a looser fitting jean, a natural fiber sweater, and a classic leather boot.

J.Crew Textured Rugged Merino Wool Crewneck Sweater

Now this is one hell of a turtleneck. J.Crew crafted it from a hearty Merino wool blend with natural speckling that really makes it sing. Trust us, you won’t get any Steve Jobs jokes in this.

Levi’s Vintage Clothing 1937 501 Original Fit Jeans

Levi’s 501 was the company’s (and the world’s) first pair of jeans, but that doesn’t mean they haven’t changed since. The company lovingly recreated their 1937 version for their Vintage line, which’ll look great with a hearty sweater.

Wolverine 1000-Mile Plain Toe Original Boot

Complete any head-to-toe workwear look with a pair of boots that can take a beating. Built to last for over, you guessed it, 1,000 miles, this Wolverine pair will do just fine.

Go All In On Cotton

It’s natural to think of super-insulating fabrics like wool, mohair, and cashmere when you’re thinking about sweaters. While there are some great wool and cashmere sweaters out there, don’t underestimate the value of a great cotton sweater — especially when you’re layering. Let your jacket do all the work in terms of warmth, and let your sweater and jeans keep things for overheating underneath.

Everlane No-Sweat Sweater

You can’t get more classic than wearing a black sweater with jeans and Everlane’s made this one from a cotton blended with Coolmax recycled polyester.

Imogene + Willie Barton Slim Nachez Jean

If you haven’t heard of Imogene + Willie, here’s the deal: They make some of the best jeans around. Take this pair: They’re made from orange-line selvedge denim loomed on Draper shuttle looms that were restored from the legendary Cone Mills.

$285 at Imogene + Willie Barton

Anonymous Ism Slub Cotton Blend Socks

The best outfits nail all the details, even down to the socks. This cozy, slub-cotton pair from Tokyo-based Anonymous Ism will make you want to cuff your jeans to show ‘em off.