How to Wear a Crew Neck Sweater (5 Fall and Winter Outfit Ideas For Men)

by Beau Hayhoe  |  in Style Tips

It’s the question that’s on everyone’s mind right now (or at least, it’s on our minds): How to style and wear a sweater when you’re dressing for cold weather. 

There are right and wrong ways to do it, so today, we’ll focus on the right way. And if you start things off with one of the best sweaters for men, it’s tough to go wrong.

If you find the proper sweater, the world is your oyster as far as versatile outfits are concerned. But what type of sweater belongs in your closet? The key is versatility. A V-neck can lean a bit dressy, while a cardigan usually feels more casual. In this article, we’re focusing on a crew neck style, the perfect middle ground.

A crew neck sweater, especially one in a heavier fabric for fall and winter, can be worn in ways both dressy and casual. A bit further down, we’ll show you five ways to wear a sweater with a balance between sharp and laid-back looks.

The Versatile Crew Neck Sweater In These Outfits

Alex Mill Donegal Crew Neck Sweater

This sweater is crafted in a superfine merino wool blend with a bit of alpaca which gives it such a soft, great texture. The donegal yarns give it unexpected flecks of color throughout for a timeless feel we love

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In this article, we’ll be using the charcoal donegal wool crew neck sweater from Alex Mill. It’s a classic fit and style. The dark grey color goes with everything in your wardrobe, and the varying dark and light flecks of the donegal yarn adds a bit of visual interest and texture.

Oh, and speaking of texture, the sweater’s fabric is a mix of merino wool, nylon, and alpaca, so it’s guaranteed to be nice and soft.

While the Alex Mill sweater will be used in each of the outfits below, we also love these two alternatives. They’re fine options and also go well with plenty of things in your Lean Wardrobe.

Everlane Felted Merino Wool Sweater

To make this wool softer, warmer, and more durable, Everlane washed and boiled the yarn so it softens and shrinks up just enough to create a denser fabric with all of wool’s upsides—and none of the scratch.

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J.Crew Merino Wool Crewneck

This sweater is blended with soft, naturally breathable merino wool with hardy nylon for sweaters that are as soft and comfortable as they are durable.

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Wearing a Sweater

If you’re unsure what to wear under a sweater, well, keep reading. But it’s important to keep that crucial versatility in mind. You can wear a crew neck sweater atop something as simple as a T-shirt.

And if you’re curious as to how to wear a sweater with jeans, rest assured that you’ve got plenty of options. A sweater can become your new go-to basic layer in cold weather, just as a T-shirt is a reliable pick with jeans in warm weather. 

Not just any old sweater will do, though. As with the rest of your Lean Wardrobe, how a sweater should fit is something to keep top-of-mind.

  1. The right crew neck sweater should fit a bit more loosely to accommodate layers.

That doesn’t mean sloppy or baggy, by the way. Think a size up from your regular size if you’re selecting a trim sweater, or simply choosing the more relaxed or traditional fit instead of the slim fit.

  1. The sweater’s shoulder seams should hit right where the shoulder bone ends.
  2. The hem should at least cover your pants’ waistband.
  3. The sleeves should end at the base of the thumb.

The key is to allow room for layers underneath without drowning in fabric.

Once you’ve perfected the fit of your crew neck sweater, it’s time to put together some outfits. 

You’re in luck: We’ve got you covered, and we’ve considered all your questions… everything from how to wear a sweater with jeans, to how to wear a sweater over a collared shirt, and much more.


What To Wear With A Crew Neck Sweater: 5 Outfit Ideas For Guys

Here are five Lean Wardrobe-approved outfits you can try with your winter-ready crew neck sweater.

The Cold-Weather Classic

Let’s kick things off with the classics in mind.

If you’re unsure how to wear a sweater over a collared shirt, well, we’re making it easier with this outfit because you’ve likely got some of these pieces in your Lean Wardrobe already.

First off, the collar goes under the sweater, not over. Keep that in mind. Yes, it should still be standing up as normal, but the collar points should sit underneath the sweater collar. Keep it all in, boys!

Picking up a charcoal sweater gives you plenty of versatility when it comes to mixing and matching. The charcoal color helps the crisp white shirt pop, while ditching the tie toes the line between polished and casual.

Dark blue denim grounds this outfit nicely, and you can never go wrong with dark blue denim. Wingtip boots are a reliable pick for cold weather as far as form and function are concerned. To protect you from the fall and winter chill, top things off with a timeless navy peacoat. 

These are all pieces you’ll have for years. Once you take off your peacoat, your charcoal sweater and white shirt will stand out subtly and stylishly, which is precisely what you want. 

An Easygoing Everyday Look

Remember how we talked about wearing a sweater over a T-shirt? It’s one easy option you’ve got in your bag of tricks when you brainstorm what to wear under a sweater. This tee adds just a touch of color to the overall look, while the merino fabric provides comfort and breathability. 

That same pair of dark blue denim can pitch in nicely alongside this casual look. Because we’re ditching the collared shirt, your trusty high-top sneakers provide comfort and easygoing appeal. It also never hurts to add some classic high-tops to your Lean Wardrobe. 

Top it all off with a cool, eye-catching hat. This particular ballcap is a serious step above your typical athletic logo ballcap. It can more than hold its own when worn with a polished-but-casual crew neck sweater. 

Rugged and Ready 

The best crew neck sweaters can hold their own against all outer (and inner) layers.

Check it out: this crew neck is being layered under a thicker and more rugged overshirt. The soft cotton chamois overshirt provides warmth without a ton of bulk, while your long sleeve tee is an excellent base layer.

Advanced-level layering? We gotcha covered right here.

Dark denim gets swapped out here for durable and tough work pants. This is your go-to look when battling the elements as you explore the city or go off-trail. Plus, the blend of a navy overshirt and charcoal sweater is a classic color combo. 

The crew neck sweater works as a nice base layer to protect against cold weather through fall and winter. Of course, rough-and-tumble work boots help solidify the rugged nature of this look. 

Don’t forget that you can repurpose those work boots and work pants and wear them with other rugged staples like flannel shirts, thermal base layers, and waxed trucker jackets for even more variety in your wardrobe. Consider mixing in this crew neck sweater to more outdoors-minded ensembles; it’ll go together nicely.

Roll Up Those Sleeves

Ever have to deal with a fluctuating A/C system at the office or at home? That’s where a crew neck sweater can play a helpful role, even in a business casual ensemble. The gang’s all here as your charcoal crew neck teams up once more with your workhorse white shirt

The key difference? We’re rolling up those sleeves and getting to work (it’s a great way to show off your leather watch, too). Shake up the typical shirt and tie look with a knit version. Knit ties provide visual interest and texture, especially one in a seasonally friendly color.

Those tan chinos you wear all the time can easily be swapped into this biz casual ensemble. And because we’re trading out the blazer for a crew neck sweater, rugged-yet-dressy wingtip boots are the right footwear move, especially in fall and winter.

Master this look, and you could become the best-dressed guy in the office (if you aren’t already… wink)

A New Daily Favorite 

Let’s bring it all together for the final outfit. You’re going to love wearing this on the daily.

Your charcoal sweater adds fall and winter-ready warmth, and it helps that ever-reliable white shirt stand out in a crisp and cool way. Of course, classic blue jeans are a foolproof style essential.

Wingtip boots, dark blue denim, and a great sweater: a favored combo of celebs like Daniel Craig (especially the blue denim / wingtips pairing). Make that style all your own, then add a bit of flair via a classic camel topcoat. 

Between the charcoal, the blue denim, the rich leather wingtip boots, and the camel topcoat, you’ve got a look that stands quietly, yet with authority. 

Master how your sweater should fit and what to wear under it, and outfits will start popping up on your mental menswear mood board left and right. 

Why You Need a Crew Neck Sweater

Think of the crew neck sweater like a fall and winter workhorse.

Consider it a cold-weather staple piece, in the same way that a T-shirt can serve you so well in warm weather. That’s because the crew neck sweater goes with practically anything and can be worn in ways both rugged and refined.

Throw it on over a comfortable merino T-shirt at the office or at home.

Naturally, classic outerwear like a camel topcoat or a navy peacoat are a perfect pairing when worn over a subtly stylish crew neck sweater. We’re talking warmth, comfort, and utility, all in one package. 

Hopefully these five outfits get you started. From here, it’s easy to think up new outfits to wear with your crew neck sweater. Your Lean Wardrobe just got an excellent new addition.