Better-Than-Basic: 3 Ways To Wear A Henley Shirt

When it comes to building a wardrobe, a henley shirt isn’t just another brick in the wall - it’s a pillar that holds everything together. One of the most versatile pieces in our collection, men’s henley shirts offer a warm base layer on cold winter days and the perfect standalone shirt for spring and summer. Super-soft and ultra-comfortable, these elevated essentials are anything but basic. For every outfit, we’ve got a henley for the foundation. 

Here are a few of our favorite ways to wear a men’s henley shirt: 

#1 - JUST THE HENLEY

No need to overcomplicate things - henleys look great on their own with a pair of stretch denim jeans or casual pants.

Christian McCaffrey in the Biscoe Striped Henley

Even the most basic outfit is boosted with the help of a henley shirt. It offers the same super-soft comfort of your favorite tee, while looking and feeling more polished and put together. Whether you choose to button all three buttons or none at all, it’s a matter of personal preference; either way you’ll look great. 

GET THE LOOK: Biscoe Striped Henley; Castleton Chino - Nashville Straight; Weston Mid-Top Sneaker

#2 - WITH A FLANNEL

Another advantage of the henley shirt is that it provides a substantial layer of warmth without adding any extra bulk. Cold? Just throw your favorite flannel over your go-to henley shirt. Add jeans and you’re good to go. 

 

When comfort is paramount but looking good and feeling great remains key, this pairing of a super-soft burnout slub henley and a stretch cotton flannel shirt is a no-brainer. Plus the pop of color is the perfect way to change things up a bit while still looking cool and casual.

GET THE LOOK: Chatham Burnout Slub Henley; Bayville Stretch Flannel Shirt; Roanoke Jean - Oakland Slim; Weston Mid-Top Sneaker

 

#3 - LAYERED UP

When the temperature drops below freezing or if it’s too cold for just a flannel, throw on a lightweight pullover for extra warmth and an added dose of style.

We’ve said it before and we’ll say it again, a henley shirt works great as a base layer with heavier layers on top. Two is OK, four gets a bit busy. But three? That’s how you master your layering game

GET THE LOOK: Elkins Slub Henley; Eastlake Flannel Shirt; Deering Quilted Snap Pullover; MadeFlex Clutch Comfort Jean - Oakland Slim; Weston Mid-Top Sneaker

 

We hope these men's henley shirt outfit ideas give you some inspiration. Want even more tips and tricks on how to put together comfortable and casual outfits that look as good as they feel? Check out our Shop The Look page.