The Turtle Won the Race

March 17th, 2011

Turtlenecks have gotten a bad rap. For whatever reason, more men are “afraid” of the the turtleneck shape than any other classic silhouette in menswear.

Ironically, when pulled off correctly, it can be one of the most chic and elegant pieces in a man’s wardrobe.

Redford, Newman, McQueen, Connery…the list goes on and on for style “icons” who were known to embrace a good turtle.

Here, four different styles for four different looks.

    1. Chunky, Cozy & Manlier Than You’d Expect


    Turtlenecks, in general, work better on the slim (and best on the tall and long-necked). On heavier guys they can draw a little too much attention to the neckline  – which usually isn’t a bigger guy’s best feature.

    I like this one in particular because when I first came across it it looked like sh-t. I found it drooping off of a shirt hanger at the Hugo Boss outlet in my hometown and my boys all thought it was “wack”. Once I put it on though, their minds changed and it’s now one of my favorite sweaters.

    Where I wore this: Knicks game.

    Bonus Tip: Every once in a while its a good idea to try-on things that you wouldn’t regularly consider. Try-ons are free and sometimes you’ll be surprised at how flattering a piece can be. Take it a step further and bring a friend (whose opinion you can trust) and have him/her choose pieces for you to try-on. Stay open minded.

    Bonus Tip II: A chunky knit turtleneck – especially in cashmere – is about as comfortable as it gets for late winter/early fall. It’s like wearing a fitted blanket (you know how sometimes when you’re a little chilly you just want to pull the blankets all the way up to your chin… yea).

    Bonus Tip III: Put sweater on, then style hair – not the other way around.

    • Cashmere/Angora turtleneck sweater by Hugo Boss
    • Burgundy down vest by Gap
    • Bracelets from NYC street vendor
    • Olive fingerless wool gloves from Army/Navy supply store
    • Brown corduroys by H&M
    • Brown wool blend socks by JCrew
    • Brown leather captoe boots by Kenneth Cole

    2. Thin, Fitted & Dressy


    A fitted fine-gage turtleneck in a solid dark color is about as “dressy” as a sweater can get – without having to layer it over a dress shirt. Wearing one under a suit (especially a double breasted suit) is an underrated Italian-inspired look.

    Where I wore this: Columbia University alumni charity event.

    Bonus Tip: If you’re dressing-up a turtleneck, make sure the neck roll is clean and even. Flip it all the way up over your nose, then fold it evenly and flat all the way around. Once it’s folded in place, it shouldn’t move.

    Bonus Tip: This, in my brief opinion, is the future of suiting. Light canvas, no lining, no shoulder pad, “Neapolitan” shoulder, etc. This unstructured jacket is so light and comfortable (without sacrificing shape or drape) that you could throw a touchdown in it. In a more relaxed fabric (cotton or linen blend, for example) these new age “leisure suits” work as well with sneakers as they do with ties. Much more on this coming soon…

    • Navy fine-guage turtleneck by Uniqlo
    • Grey flannel double breasted suit by d’Avenza
    • White cotton pocket square
    • Watch by Montblanc Timewalker Automatic
    • Brown alligator watch band by Montblanc
    • Leather/suede double monkstrap shoes by Scarpe di Bianco

    3. Clean, Simple & Striped


    Looking for a simple, elegant and masculine look that is easy but looks “put-together”? Go with a substantial turtleneck (with or without a simple pattern) and a pair of classic flannel trousers. On a day like today (59 degrees, partly sunny) that’s all you need.

    Where I wore this: meeting PR representatives/picking out the pieces for the 2nd givea-away (coming soon!).

    Bonus Tip: One disadvantage of turtlenecks is that they are a pain in the ass to put-on and take-off (especially if you style your hair in the morning, like me). Therefore, consider where you are going/what you will be doing. If you have to sit for a while in a warm room, you might be in a tough spot.

    • Tortoise shades by Persol
    • Wool/Cashmere turtleneck sweater by Brooks Brothers Black Fleece
    • Grey flannel suit trousers
    • Oxblood boots by Scarpe di Bianco

    Thanks for reading.

    Yours in style,

    Dan Trepanier

    Photography by Alex Crawford.

    • Mike

      How do you guys feel about irish knit aran sweaters?

    • Agnes

      simple and best post…

    • E. Honda

      What about Steve Jobs? He had the best turtleneck style of anyone.

    • Esme

      Wow…speaking for the lady readers: hot! Especially the last pic. Only exception (#2) is that purple linen pocket square…

    • Oscar Navarro

      I am a new reader and I love your blog. Great sense of style.

    • obell

      gloves in number 3 are rockin. nice work

    • Michael

      Look 4 is one of your best ever. Simple but perfect.

    • khordkutta

      How big a pant cuff is that on look 4? 2″ or so?

    • khordkutta

      looks 2 and 4 are on point. I have always liked rockin t-necks, especially with a vintage coat, makes me fee like “Shaft” or “James Evans”

    • Joe schmo

      I must say I appreciate the vindication for puffer vests. I have a particular friend who refuses to address me as anything other than “HEY MCFLY” when I wear one.

    • Christian

      I love the brown suede monk straps sir…

      Best Wishes,


    • Mike

      Somehow you can turn everything into a fashionable piece. Look 3 is amazing. should try that sometime.

    • Mr. Andy

      Irt your “future of suiting” opinion/prediction: I wouldn’t be surprised. I own a cotton canvas “urban safari” jacket that matches your description and acclaim. This type of jacket could definitely be the gateway drug jacket for the guy (or gal or trans) whom would otherwise be less inclined to don a trad suit. Great foresight.

    • Bosun

      I have always been a secret admirer of the turtle neck, especially as worn in looks 2 and 4, to give a smarter look. But i didn’t realise how good they can look when combined with a Gillet/Vest/Bodywarmer (too many terms for one single item!).
      Seriously thinking about getting one thanks to this wonderful post!

    • russbheez


    • bill

      “it’s a cosby sweater- a cossssby sweaaatahhhhh”

    • J A Shepherd

      The roll neck (as we call it over here in England) is under used I feel by guys and therefore when you where one, as I did last night to a magazine birthday party, you get a lot of comments. If you don’t own one go and find yourself one.
      SB great work my good man and keep it up. I have been meaning to comment on your blog for sometime but have only just got round to doing so.

      J A Shepherd

    • DCRob

      Tsk Tsk Tsk…Bonus tip #3 regarding your first look…You broke it! You styled your hair pre-sweater:

      Hahaha..I am ashamed I remembered this look from that video. Great post as usual, Dan.


    • Robin

      All the looks are really great!
      I’m really loving the layer work in look 3.
      Keep it up!

    • John Ryan

      Not a turtleneck guy. Never will be. They just look friggin’ weird on people…

    • Where?

      SB loving the turtles! look 3 is awesome, but i am having trouble finding a loose turtleneck. Do you think that major stores i.e. Gap or J. Crew have them or only smaller designer boutiques?
      thanks for the help
      keep the posts comin!

    • choosum

      agreed, look 4 is fantastic

    • cam

      as always i really appreciate the work you continue to put into your blog. i especially like the writing and tips. that last look is perfect however i must say one can only hope that you are wrong about the future of suiting.

    • KLEE

      Number 4, so fresh and so clean clean

    • Terrence

      #2 and #4 are very clean and put together well. Both are good looks.

    • Mark

      What ever happened to the Mock Turtleneck?

    • Sean Maurice


    • Ryan

      Look 4 is by far my favorite. Well done sir. The turtle-neck fits perfectly on you. Very nice look.

      • Sid

        Look for is cool. The trousers are awesome, just the right measure of slim-fit and pleats!