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.


    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).



    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


      Take me to the Shop

      • jbird669

        I’m going to use that Henley/waistcoat combo this fall!

      • Bo

        Loved your post detailing the business of blogging and your decision to hop into the production side; now that I see that last suit, I’m excited! Think it’s very cool what you’re doing, much respect. Also: I do love a great short-sleeve henley in the spring & summer and have been layering it under a slim blazer and dark denim; I think the tailored get-ups look excellent!

      • JoeFromTexas

        How do you get that rust DB to look good open, rather than look like you’ve got an ill-fitted cape flapping all around you. Me and David Letterman seem to have this problem, though when Letterman did button up his DB’s, they looked a lot better than mine do, which I keep buttoned. Is it just a slimmer distance between columns of buttons?

      • Sam Parr

        Great feature, and i’ve been loving the new things you’ve been doing, but could you please stop referring to every garment under the sun as “the tailored such-n-such”. It’s just a bit too iGent for me and others i’m sure. Don’t get me wrong, i’m all for descriptive adjective, but don’t you think it’s starting to seem a bit like overuse? I think it’s definitely gonna be old once you do an article about “the tailored jockstrap”. Just a small complaint. Otherwise good content overall.

      • Ethan W.

        Loving the last suit Dan! Do you do payment plans for your upcoming line?;)

        • jbird669

          In all seriousness, will there be a payment plan?

      • AdamE

        Henleys can be great… but can be woefully abused… The challenge is, it’s a shirt that everyone puts on and feels like Ryan Gosling, when in reality many of them look more like Borat, with a big poof of unsightly chest hair creeping out over the opening… To really pull off the Henley it’s a fine line between looking good and looking “very nice!”… Much like deeper V t-shirts…
        That said, all of the looks in this piece are spot on, and i love the idea of pairing a casual piece such as a henley with other tailored pieces to hit that sweet spot where you’re seldom under-dressed, but never over-dressed…

        • Simon

          Exactly my thought. I never felt comfortable wearing deep v-neck, henley or any other garment revealing too much of my chest. I’m not exactly a bear but my chest is quite hairy since I have black hair (they tend to be more obvious). I see men wearing them with big foxtails coming out under their chins… Come on !

      • Scott W

        I’m throwing money at my screen trying to get that rust suit! Do you have the fabric ID for that blue herringbone? I looked through the Ariston books and didn’t see it. Any insight on to how silk/linen holds up? I’ve heard to go with wool/linen if possible because it adds durability and wanted your expert opinion. Thanks DT!

      • Will

        This is my favorite genre of AoS posts. Dan takes a classic clothing item – in this case, seasonal suiting – and updates it with a contemporary spin. Nothing too adventurous, nothing too staid, just right in that casually-tailored sweet spot. The biographical aside about starting off at Michael Andrews Bespoke is a great kicker (posts that delve into the site’s backstory and how Dan got his start in the industry are another thing I consistently enjoy). I know every entry can’t be about Dan showcasing his baller wardrobe, but these are the features that keep me coming back to the site.

        • JBells

          i could not agree more!

      • Franklin

        Dan…you may not want to give away the secrets yet, but do you have an estimated price point of your upcoming collection or do we have to wait and see :)?

      • olrichm

        I can’t wait for your collection, that last suit is so perfect! I really enjoy the henley/sweater with a casual suit look. For me it’s a look that doesn’t require some occasion, which means I can use it more often!

        • Brittany_StyleGirlfriend

          That suit is the epitome of dapper – cannot get enough of Henleys with suits or worn with a casual weekend look!

          Brittany |

        • tommyjohn_45

          Couldn’t agree more… That suit’s got me pumped to see the first line of AOS!

          Nice post, Dan.. Love a good henley, and love seeing new ways to dress down a suit. cheers.

          • Dan Trepanier

            Thanks Tommy John! Nice meeting you in NYC. Keep keeping it real

            • tommyjohn_45

              Likewise… Great event all around. Would love to get a copy of the photo Alex took of you and I after you took home the title! haha

        • Dan Trepanier

          Thanks brother. We’re very much looking forward to it as well :)

      • Miguel

        Love me some Henleys, they’ve become part of my weekend life, specially when you find them in linen or fine cotton, they’re just super comfortable and fresh.

        • TO

          Where have you found linen ones Miguel??

          • Miguel

            TO, mostly online and I found one at a Century21 Store.

            • TO

              Oh ok any particular online Venues Miguel? Thx bud

              • Miguel

                HauteLook has daily sales, sometimes they have a brand that has Henley or a sale of Henley only.

      • cam

        hey dan, ive been wearing henleys all summer long with tropical weight trousers myself. i havent incorporated the waistcoat but i may gve it a run. would you stick to a long sleeved henley with the waistcoat or would short sleeved be ok? congrats on the bespoke offerings coming! the first sneak peek looks great. all the best..

        • TO

          I would imagine short sleeves to look a little incongruent with a waistcoated look… Never experimented though, I would think of trying to keep the Henley’s fabric luxe to try too offset the casual-ness of short sleeves might work

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