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 wool blend socks by JCrew ·
  • Brown leather captoe boots by Kenneth Cole
  • · Brown corduroys by H&M

Pima Corduroy Trouser in Chestnut

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 ·
  • Oxblood boots by Scarpe di Bianco
  • · Grey flannel suit trousers

Wool Flannel Trouser in Mid Gray

Thanks for reading.

Yours in style,

Dan Trepanier

Photography by Alex Crawford.