Long Sleeve Henleys: A Must Have For Winter

You probably have a stack of crewnecks and V-necks in your closet in all sorts of colors and with various graphics.

But with the winter just around the corner, you might be truly missing out on the ultimate men’s fashion must-have, the long-sleeve Henley!

It’s the perfect layering piece that looks just as good on its own as paired with other wardrobe staples, and it solves the neverending problem of “what to wear” in a heartbeat.

What’s a Henley

Henley is a collarless tee that has a placket with two or three buttons that go vertically from your neck. The tee is usually made from soft fabric (softer than the classic t-shirts) such as cotton, cotton blends, cashmere, etc.

The most common version of the Henley has long sleeves and dates to the 19th century when it started as a uniform for laborers and then English rowers.

How to choose it

A long-sleeved Henley t-shirt is super versatile, and if you pick the right fit, style and get a few colors, you will have many great ways of wearing it.

Fabric. We recommend opting for natural and breathable fabrics such as cotton, cotton-polyester blends, and thermals for those freezing days.

Fit: If you’ve seen a photo of Ryan Gossling, the patron-saint of Henleys, you’ve probably noticed that his tees are never baggy or sloppy. Take note and choose a tee that accentuates your body, shoulders, and chest yet isn’t too tight. The best length is just below the belt.

Color: You’ll never go wrong with classic colors such as grey, navy, burgundy, black or off-white. These are easiest to style with you any other clothes and are flattering to everyone.

Quality. It should go without saying, but here it goes – always get just high-quality tees from trusted brands like Fresh Clean Tees. They do the hard work of choosing the best colors and fits for you!

Wearing a Henley its own

Henley tee looks excellent when you wear it on its own; that’s the beauty of this style. It’s simple, casual yet still shows that you put some thought into your appearance.

With chinos

Chinos are beloved whatever the season, but they’re especially popular in winter as the base of most men’s everyday looks.

Pair your Henley with these trousers, and you have a great smart-casual outfit for work or weekend lunch with friends.

Best color combos? How about navy chinos and a burgundy Henley or dark grey bottoms and a charcoal tee?

With jeans 

Henley and denim trousers. It’s the ultimate bro-night look! We love how the Henley adds a level of sexy to your blue or grey jeans, making it an outfit and not just something you threw on.

Finish the look with warm leather boots and a beanie if you’re feeling cheeky.

With wool trousers

Wool trousers are the men’s fashion underdog and so great for winter. Many guys avoid this garment, though, as it feels too formal, but here’s where your Henley comes in!

These two pieces balance each other out and create an outfit fit for the office and date.

Pairing the Henley with other pieces

Let’s move to the second part of styling your Henley – pairing it with other pieces.

With a cardigan 

We love cardigans for winter as they’re the more casual (and warmer) version of a jacket.

The long-sleeve Henley is the ideal layering piece for this look as it adds to the relaxed emotion of the outfit, yet it’s still appropriate for the office.

With a button-down shirt 

A classic lumberjack look or inspiration from the early 2000s? Whatever the case, a shirt plus a Henley is a great outfit for the weekend or an evening at the pub.

It’s relaxed, comfortable yet not sloppy; what else do you need?

With a blazer

A long-sleeve Henley is an excellent substitute for that stuffy shirt under your everyday blazer.

Here’s a winter office look you’ll never want to change: a grey Henley tee, navy blazer, and charcoal chinos!

You can also pair it with jeans for a more casual style.


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