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.


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

    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.


    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.

    • BM

      Light colored polo under dark colored henley goes pretty well

    • Ian

      What about a henley with a shirt and tie? Is this do-able, and if so how would one pull it off?

    • chris fields

      is your fly undone in the “sockless” photos???

      • SB

        Hi Chris. It’s a button fly…looks like maybe one button came undone.

        Thanks for reading, and for your concern.


    • paul fredrick

      I love the article way to go. Its really good

    • Ariel…

      Amazing post! Floral Henley is epic. I really do think that floral pattern can be extremely manly when worn in small doses. It was pure inspiration on the third look with the henley over the Oxford. As always, looking forward to your future post. Check my blog at BRO!

    • Kristopher

      Hey Dan, I’ve actually got a question totally unrelated to this post. I’m looking at buying a pair of PRL Boots (I kno I’m late but I love them) and I’m wondering if you know anything about their sizing. Basically I want to know if they run true to size or if hould size down a half size like in bean boots. Any insight is grtly appreciated. Thanks.


    • James

      I put a vneck shirt (one with a high v) under my henley and it looks cool. I like to think I came up with it, but i actually stole it from Jay Z. But I am more ripped than Jay Z, so I look better than he does with a higv vneck under my henley.

      • James

        p.s in pictures 3-4 your fly in undone

        • SB

          Missing one of 4 of the fly buttons in look 2. Fully buttoned in look 3.

          Thanks for reading,

    • DP


      Nice work brother. While I love these posts, when are you going to some on fits, tailoring, etc.? I know you did some of these on your old blog, but I think a lot of people have difficulty with just the fit of their clothing.

    • scarf tying

      UH-oh! so adorable! my boyfie must follow this style. surely, girls will envy me hahaahhaa :))

    • Mark

      I really like #2, where are the pants from?

    • Julian

      These looks are fab! Well styled! :) Way better than the sneaker suit combination on last post.

    • Dane

      Hey can you still purhase that flower henley? Just curious or do they not offer it anymore?

      • SB

        I doubt it, I picked it up off a clearance rack years ago.

        The point is – don’t look for the same one, rather be open-minded to pieces that you wouldn’t normally think to style into your wardrobe.


        • Dane

          Yeah I got that, I also appreciate how you shop your closet. So many people any more don’t do that, they’re missing out.

    • sincere


      Great post. When you say “Michael Andrews Bespoke (custom made, my own design).” I love your work. But what does my own design mean. Do you design the actual pattern on the fabric.

      Also, love the first pic with the printed knit half tucked in the pants showing the belt. I never seem to know how much to tuck into the pants to show enough belt.

      Brown belt with green shoes is awesome too.


      • SB

        Thanks for reading.

        I don’t physically draft the pattern, but I dertemine all of the dimensions and structures that are used to create the pattern – in order to achieve the fit and feel I’m looking for. I also hand-pick each of the inputs (fabrics, linings, trims, buttons, canvas size and shape, shoulder pad dimensions, sleeve headers, thread colors, stitch lengths, pocketing fabrics, etc.) as well as each of the styling dimensions (lapel style & width, rear venting, pocket flap sizing, pant waistband style, etc.)


        • sincere

          Thanks Trepanier.
          I knew you are a genius of fashion.

    • TO

      To me #1 is a pretty perfect casual look- makes me excited to look for hidden gems like that henley!

      • SB

        Thanks brother. Hope all is well.

    • JMRouse

      Really digging look 1 and 2. Surprised how good look one looks. I am sure if I say that henley on a rack I would pass it up, but you are right that pulled together it works. Great tips.

    • dish

      Is that some zipper sprezzatura in look 2? LOL.

      But anyways, great post. I love henleys…definitely need to get myself more of them.

      • SB

        I think I’m missing a button on the button-fly. Not purposely, sh-t happens.

        Thx for reading,

    • Brian

      Dan… love the site brother. I was wondering what color of the Shwood shades you are wearing in the above picture and are they comfortable to wear? I’m really diggin’ those! They look awesome for summer.

      • SB

        This pair is the Canby in Zebrawood with brown polarized lenses. They feel great.


    • Travis

      Love your style as always – can’t get on board with the graphic henley though – a little too Jersey Shore for my taste. Keep the posts coming though, your blog is a treat.

    • Michael

      Like first two looks a lot, third is a little off IMO-too many buttons.

    • Anonymous

      Henleys are great. I often wear mines on their own or under casual plaid cotton sports jacket.

      • SB

        Thx for reading.

    • WM

      Killer post! The green oxfords in look one are amazing. I’m really enjoying your frequent posts and am very excited for your personal line to come out!

      • SB

        Thx! The “hulksters” are one of my favorites pairs. Literally one of a kind.

        Much more on the line coming later this month!


    • Anonymous

      A good alternative to the LL Bean shoes in the second look is:

      • SB

        The driver is an all together different shoe, in my opnion. But thanks for sharing.


        • Anonymous

          Agreed, but it does give of a similar vibe don’t you think?

    • Henri

      Man your style kills. Kudos on the post.

      • SB

        Thx Brother

    • David

      You know who else likes to wear that casual shirt over button down look? Neil Strauss also known as the pickup artist Style. Blech! Don’t do it.

      • SB

        Thx for reading

    • DCRob

      The brogues in the first look kill it. The second look is the overall best look IMO. The third look throws me off a little bit. Maybe it’s the the shirt under the henley makes the henley look like a damaged sweater, IDK??

      As always, I appreciate your posts Dan.


      • SB

        Thanks brother. Not sure what you mean by damaged sweater, but 2 of 3 ain’t bad. Everybody has their opinions.


        • DCRob

’s hard to explain, from afar it looks like a worn out sweater. I think the color of that henley could stand alone without the poplin underneath. Still great looks.

    • D Knott

      I hated henleys until i saw them on this site. Still not a huge fan but i will give them a try.

      • SB

        Took it from “hate” to “give it a try”…I’ll chalk that up as a W :)

        Thx for reading,

    • Ali

      I have to tell you that I’ve been obsessed with the Club Monoco quilt jacket since I saw it on your site several posts ago and I have been looking for something like it since. on Monday, I finally found a piece I liked. It’s a Barbour x Tokihito Yoshida collabo: (my own photo blog). It fits great, great quality, I hope you approve!

      • SB

        Thx for reading!

    • SD

      SB, you nailed it here!

      I seem to remember the first look from your most recent video! I love it. Most guys wouldn’t think twice about a vintage flower-print henley, but you pull it off easily.

      You have definitely given me some inspiration. Thanks as always for your hard work.

      • SB

        Yup, we shot the photos and video scene on the same day.


    • Miguel Ramalhão

      I had never thought of the henley like that. Very cool tip …. I’m definitely gonna give it a try…

      • SB

        Go for it!

    • Kees

      In the Netherlands we call these things “granddads”. I’m not sure why. I like the first and third looks a lot. The pocket square in the third is a nice touch, although i would go for a different color, maybe light blue?

      • SB

        Interesting… Thx. Light blue would certainlty work

    • Dan Lau

      are you tucking in just the front of the henley to show the belts? I have thought about doing this with cardigans or sweaters because I like the look with the belt better but it just never looks right. good looks.

      • SB

        Thx Dan

    • Todd

      Love every look. I was just looking for light layering pieces as it gets slightly warmer here in Montana. The first look is terrific for spring! I really like your jeans in the first look. Were they that slim from Polo or did you have them taken in?

      • SB

        Thanks Todd. The jeans haven’t been altered, just a good slim (but not skinny) fit by PRL

    • alan m.

      Great post. My style icons are Jfk and his son.
      I have to say you are slowly becoming a style icon
      in the making. Wishing you lots of success.

      • SB

        Thx for the compliments Alan

    • Josh

      Who makes the pants in the second look? I’m looking for a grey like that.

      • SB

        Helmut Lang. Thanks for reading!

    • Mike

      I have exactly one off-white Henley shirt (made by Ben Sherman). Must break that one out soon. I know this is a post on Henley shirts but I have to say that I LOVE the cuff and no break on the pant length in the last photo.

      • SB

        Go for it. Thx Mike!

    • Swashbuckler

      Henleys forever <3 All three are great– especially the first. Bravo!

      • SB