The Tailored Henley

August 11th, 2015

A henley is a collarless pullover knit with a placket at the bottom of a round neckline, usually having 2–5 buttons. This particular style of shirt was the traditional uniform of rowers in the English town of Henley-on-Thames, hence the name henley. In fact, many rowing teams still use this style as part of their uniform.

Basically, the henley resembles a collarless polo shirt. The sleeves may be long or short and it can be made in almost any fabric; from military grade cotton thermal, to luxurious cashmere, to lightweight linen/silk blends.

In my opinion, a simple henley is a foundational garment for a man’s casual wardrobe. It’s one of those core pieces you can really build around. The body-forming fit and open neckline have a certain casual nonchalance, making it a perfect match for dressing-down some unstructured tailoring.

To get you thinking, here are a few examples of the “casually tailored henley”.

Silk Suit & Cashmere Henley


If the henley is short enough to hit just a few inches below the waistband (like this cashmere block-stripe) then leave it untucked with a seasonal suit (like this silk/linen herringbone).

A low-top pair of Vans is sleek enough for a seasonal suit, just make sure the hemline is narrow and cropped enough. No breaks on sneakers.


Marine Linen Suit

Hopsack Waistcoat & Linen Henley


Olive, rust, khaki, brown…gotta love earthy color palettes, especially in lightweight fabrics like linen, hopsack, and chino.

The henley/waistcoat combo has been a go-to this summer. It’s easy, comfortable, and suave (in my opinion, of course).


Rust Hopsack Vest

Khaki Cotton Trouser

Worsted Suit & Ribbed Henley


Here’s another henley/waistcoat combo, this one navy-on-navy with a cotton waffle thermal and the waistcoat & trousers from my very first bespoke suit.

I bought this navy bespoke suit (along with 3 others – medium grey worsted, navy chalkstripe flannel, and khaki summer cotton) in 2007 during my junior year of college. I sold almost-literally everything I had on eBay (and ate peanut butter & jelly sandwiches for over a month) to pay the first-half deposit on my first bespoke order with MAB. I was their youngest client at the time, and the only client to ever go on a “payment plan” to pay the second-half deposit. After defaulting on my monthly suit payments (while juggling a college basketball career and an Ivy League academic load) I offered to work part-time in the shop (sweeping floors and fetching lunch for the tailors) in order to pay-off my clothing debt. Long story short, that is how I got into the tailoring business and started learning as much as I could… The message here: it’s not about how you start, it’s about how you finish.

With that said, to this day, this midnight navy wool suit is still on of my favorites. It may have to do with the sentimental value and all the memories associated with the struggle, but it also still looks and fits great. Thanks again to Michael and the team at MAB for all the love over the years.


For the wardrobe credits from this look, check out last week’s editorial: The Return of the Belgian Loafer.


Hopsack Suit & Cotton Henley


Switching gears here, this is officially the first “sneak peek” of the online bespoke collection we’re dropping this Fall! This unstructured DB suit in rust hopsack will be part of the collection, along with a full offering of seasonal suits, sportcoats, trousers, outerwear, shirts, etc. Everything will be handmade here in America and every garment purchase will include a basted fitting overseen by myself and our experienced tailoring team.

For the past 12 months we’ve been developing a whole new way to design, measure, and fit bespoke tailoring online. But before I give too much away, let me just say that we are very excited to be your one-stop-shop for all things menswear and tailoring. More on that soon.

  • Round sunglasses by Vint & York ·
  • Rust hopsack suit by Articles of Style ·
  • Beige henley by Ralph Lauren Polo ·
  • Pocket square by General Knot & Co. ·
  • Watch by Montblanc Timewalker Automatic ·
  • “Van Damme” Belgian style loafers by Paul Evans

Thanks, as always, for reading.

Yours in style,

Dan Trepanier

Shop Custom Menswear Made in America

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