Is your winter wardrobe feeling a bit … bland? In need of something different?

Maybe a fresh layering combination – like a new sweatshirt?

That’s what the latest Five Ways to Wear One entry is tackling.

We’re taking a staple piece once relegated to the gym — and bringing it into the light in a few unexpected ways (five, to be exact).

The classic crewneck sweatshirt certainly has athletic-inspired roots. But you can wear it in a decidedly modern fashion nowadays. The silhouette has even popped up recently on runways thanks to the inimitable Mr. Todd Snyder.

The Iowa-born fashion designer does a great job at appropriating sportswear classics for the modern man – including the crewneck sweatshirt seen here.

It’s part of the designer’s ongoing partnership with Champion. That means you get a nice mix of throwback style and downtown New York cool.

But don’t let all this “fashion” talk scare you away. Even brands like Old Navy are making simple crewneck sweatshirts with the best of them.

Reliable standby J. Crew also makes a nice classic crewneck sweatshirt with a pleasing heather grey color and a reliable fit.

And of course, you can’t go wrong with the Todd Snyder x Champion Crewneck Sweatshirt we’re styling today. But before we get too far ahead of ourselves, let’s dial in the fit.

Finding the right fit – and caring for your crewneck sweatshirt

If you’ve kept up with the revamped Effortless Gent Perfect Fit series, you’ll recognize that dialing in the silhouette of your sweatshirt is crucial.

As we’ve discussed, keeping things relatively trim is a wise move. That’s despite the French terry cotton fabric and casual nature of this sweater.

You’re looking for a high armhole and no excess fabric through the sides, for starters.

This way, you can layer something like an essential chambray shirt with ease under your sweater. Or you can go a more casual route with a merino long-sleeve tee.

At any rate, avoid the sweatshirt hitting too far below your belt line. Again, reference our new rules of perfect fit for help.

So, your sweater fits just perfectly. Great – but how should you care for it to ensure it lives up to your investment?

The brand recommends machine-washing this sweatshirt. Be sure to do so on cold and with like colors (wash your indigo denim separately – trust us).

Machine drying can – at times – cause shrinkage. But from personal experience, this sweater has held up just fine after running through the dryer (see, it’s EG-approved!).

You can also hang-dry it – but who doesn’t love putting on a warm sweater right out of the dryer?

How to style it? It’s as easy as the five outfits below – and all the combinations that you can dream up from there. Join us for the ride.

#1. Everyday, Rugged Classics

Five Ways to Wear One: Crewneck Sweatshirt

It’s tough to beat an outfit that merges most of your favorite men’s style essentials. Start with this classic crewneck sweater.

Then take a unique light chambray shirt and offset it with rugged, well-made dark denim from esteemed American-made menswear purveyors Buck Mason.

It’s a fool-proof combo when matched up with the rugged Buxton Boot from G.H. Bass. Your favorite pair of leather chukka boots is another way to go.

Stylish and comfortable American Trench socks are a favorite of many an Effortless Gent-approved outfit. And the reliably tough and eye-catching Timex for J. Crew watch is about as great of a casual watch as it gets.

If you’re chilly, you might want to throw on a heritage-quality, naval-inspired jacket to battle the cold.

#2. The Go-To Business Combo

Five Ways to Wear One: Crewneck Sweatshirt

Don’t think you can wear a classic crewneck sweatshirt in a business casual style situation? Think again.

The trick is layering it under an everyday classic – that would be the navy cotton blazer – and offsetting it with similarly versatile and casual touches.

So, the light chambray shirt makes a triumphant return. Slim chinos from the affordably priced menswear purveyors at JackThreads are also a great pick.

Of course, we here at EG love classic GREATS sneakers. The dressy-yet-still-laidback Royale is an easy way to tie this outfit together.

If a standout watch is what you seek, a handsome leather chronograph from Todd Snyder is the way to go. The darker grey leather provides a monochromatic look and feel.

#3. The Dressed-Up Crewneck Sweatshirt

Five Ways to Wear One: Crewneck Sweatshirt

Admittedly, the whole “crewneck sweatshirt under a suit” look has been done most capably by Mr. Justin Theroux in the pages of GQ. It’s definitely a style hack worth emulating.

First off, the heightened blue of this slim suit shakes things up from a more traditional navy option (best to hang up the black suit in this case).

The layering combo works because the Todd Snyder x Champion crewneck sweatshirt is so crisp, classic, and well-designed.

Layer up with an easygoing striped tee. Offset the look with sleek, unexpected suede Chelsea boots and dressy accessories like a brown leather MVMT watch — and you’ve got a look worth trying out.

Plus, something as simple as socks with a bit of pop are the right way to finish any outfit – be it tailored or more casual.

#4. Unexpected Layering

Five Ways to Wear One: Crewneck Sweatshirt

One of the fun things about a classic crewneck sweatshirt – because menswear is fun, by golly – is layering it as you please. You’ll notice that in this instance, the sweater itself is sliding under the chamois shirt.

This particular Abercrombie and Fitch chamois shirt might be a new favorite go-to in your wardrobe. With a pleasingly tailored fit and a dusty red color that livens up winter, it’s a great way to switch up your shirting game.

The same indigo denim as seen earlier in this post can definitely pull double-duty here. And comfortable CAT Footwear boots that mix function and fashion fit right in.

Of course, a durable, casual watch never fails – MVMT Watches makes this rugged timepiece particularly well.

In all, this is the sort of look you’re going to want to wear on a snow day or a weekend coffee date – and probably anywhere else you can get away with comfortable, casual and rugged style.

#5. Off-Duty Essentials

Five Ways to Wear One: Crewneck Sweatshirt

Need a way to look great without getting suited up? We might have just found it for you.

The trick is high-low styling. Mix a classic top portion of your outfit – the crewneck sweatshirt and chambray shirt – with a very laid back bottom half.

We’re not talking baggy sweatpants, however – Mack Weldon’s lounge pants are luxuriously made and well tailored. They’re cut more like a pair of chinos or suit trousers than any lounge pants you’ve tested out before.

Of course, a classic, tough field watch is both casual and crisp enough to work with this ensemble.

Well-made, affordably priced GREATS sneakers add a bit of go-anywhere appeal to this outfit. Leave the athletic sneakers at home, folks.

Plenty of Versatility

And with that, we’ve wrapped up another Five Ways to Wear One entry. Believe it or not, a crewneck sweatshirt can be among the most versatile cold-weather layering pieces you’ll add to your closet.

Seriously, there aren’t many sweatshirts that work just as well with lounge pants and sneakers as they do with a suit.

The key is finding the right sweatshirt for your build, dialing in the fit, and teaming it up with everyday menswear essentials.

Are we on the same page? Let us know how you’re planning on wearing your crewneck sweatshirt in the comments below.

Are you a fan of these looks? Any pieces you’d add or subtract?

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11 Responses

  1. Chris on

    Funny that you posted this today…Just got the Brooks Brother Red Fleece Grey Sweatshirt shipped to me last week (It’s in their clearance section right now!). Wearing pretty much exactly look #1 before I get in the car to head out for a long weekend.

    Reply
  2. HN on

    Here’s the thing… you can easily get an affordable grey sweater for cheap. Just gotta look. Make sure the fit is spot on. Look out for any sweaters that create the dreadful muffin top. I’m thin, and if I wear the wrong fit seater, I’ll get the dreaded muffin top. I also recommend finding one with small arm holes and thin sleeves.

    You can wear these with almost. anything, and it’ll make you feel comfortable too at the same time. In face, I wore mine yesterday. Pair it with a white i for button down, and you’re golden.

    https://uploads.disquscdn.com/images/26e664080b6bdc529828595f51d239a0b9f440c7437a5bdeaebb1a90f8d0eb24.jpg

    Reply
  3. Amyklas on

    Let me just say that is the post that finally made the “lean wardrobe” concept click. I have always thought each shirt is worn one way (while totally thinking the opposite of denim for some reason). Seeing the ease of use with just a couple different items here really got me going. I’ve since picked up a plain gray sweatshirt and started purging the unnecessary items. I’m also focused on “loving” and not just “liking” anything I buy. Thanks for this!

    Reply
  4. Tiffany on

    Love these recommendations! My hubby loves wearing crewneck sweatshirts and he adds an edgy vibe to it by wearing a piece from Deific Jewelry. Right accessorizing will make crewneck sweatshirt really stand out! Thanks a lot for this wonderful post.

    Reply

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