Three Ways to Layer a Henley

April 13th, 2011

There are only so many layering pieces available in classic menswear. We don’t have the selection that women have, therefore we need to be a little more creative with how we put together the pieces that are available.

Henleys, in my opinion, are very underrated as layering pieces. Everybody owns a crewneck sweater, a v-neck sweater and probably a cardigan too. But don’t sleep on the henley.

The best part is, they work as well on top of a shirt as they do under.

Here, 3 layered looks featuring henleys.

1. Casual Topper



This is one of those pieces I’ve had for years that I kind of forgot about. I make it a point to only keep clothing that I actually wear, this one just got lost at the back of a closet somewhere.

Funny thing is, this is probably one of my most complimented knits – but like many of my favorite pieces – I found it at a discount store on a rack of stuff that nobody wanted. I was like $4 or something. It’s the type of piece that doesn’t look like much alone on the hanger, but when styled correctly can really tie a look together.

Bonus Tip: Don’t write-off a potential purchase until you’ve really considered how you could potentially style it. For example, a lot of guys wouldn’t think they could pull-off a cream henley with pink flowers, but pair it with a classic navy quilted jacket, brown check shirt and roughed-up jeans and suddenly you have a look that is masculine and handsome.


Bonus Tip II: You may have noticed that I wear this belt a lot. Just goes to show that if you find a good slim, casual brown belt, it goes with just about everything. In fact, I’m wearing it in all three looks in this post.


Brown Gingham Shirt

  • Navy quilted jacket by Club Monaco ·
  • Floral henley by Ralph Lauren ·
  • Brown Leather Belt by Banana Republic ·
  • Blue washed jeans by Ralph Lauren ·
  • Green lace-up shoes by Churches
  • · Brown Gingham Shirt

2. Updated Undershirt



Swap out your typical white cotton undershirt for a light, neutral colored henley. The added texture and heft is a subtle touch that transforms a simple shirt to a layered look.

Bonus Tip: A henley with a shorter placket (less buttons) works better under, while a deeper placket looks better over.

Bonus Tip: Not comfortable going sockless just yet? Invest in some low-cut “no show” socks (although you can kind of see them peeking out here).

  • Wooden shades by Shwood ·
  • Navy washed cotton shirt by Steven Alan ·
  • Beige henley by Ralph Lauren Polo ·
  • Brown Leather Belt by Banana Republic ·
  • Slate chinos by Helmut Lang ·
  • Leather blucher mocs by LL Bean ·
  • Red Chambray scarf by The Hillside

3. Makeshift Three-Piece


Even in an uptight office, this is a casual Friday look that business folk can respect. The best part is, remove the jacket, roll the sleeves, and you just went from the office to, well, just about anywhere.

Bonus Tip: The size of the buttons affects the look of the henley. Big buttons (like the henley in look 2) are generally more casual, while shirting-size buttons look dressier and therefore work better under a suit jacket.

Bonus Tip II: When wearing it over an open shirt, unbutton the henley just enough that it’s neck opening flows with the opening of the shirt collar (in this case 2 out of the 4 buttons undone looks the most appropriate). Buttoned too high can look stuffy and unbuttoned too low looks sloppy.

Bonus Tip III: When wearing a henley over a tie, only unfastened the first two buttons to give a “v” shape at the neck rather than letting the neckhole flop open.

Bonus Tip IV: Henleys also come in short sleeve, post on this coming this summer.


Blue USA Oxford Shirt

  • Tortoiseshell sunglasses by Persol ·
  • Brown Donegal Tweed Suit ·
  • Burgundy henley by Ralph Lauren Polo ·
  • Brown leather wingtips by Scarpe di Bianco ·
  • Watch by Montblanc Timewalker Automatic
  • · Blue oxford cloth shirt by Thom Browne

Thanks, as always, for reading. If you have any questions about our online custom menswear, feel free to contact us anytime. We look forward to serving as your personal tailor and stylist. 

Yours in style,

Dan Trepanier

Photography by Alex Crawford.