Timeless American Classics feat. Gagan Singh

June 11th, 2011

Prep style is rooted in tradition and built on a foundation of staple menswear items.

With that said, everything changes (at least a little bit) with time. Therefore fashion designers and style enthusiasts alike are constantly trying to reinvent these “classics” to modernize them and make them their own.

Here Gagan Singh, the very stylish NYU senior featured previously here in our reader style post, shows us how he puts his own spin on timeless prep staples.

1. Blue Blazer & Dark Denim



“I’d say this is my go-to outfit because I can wear it just about anywhere and be appropriately dressed.

I opted for a pale pink oxford (with complimentary pocket square) as opposed to the typical white, just like I went for the espadrilles as opposed to the usual top-siders or loafers.”

Bonus Tip: “I think every man should have at least one well-fitting blue blazer in his closet.”

2. Gingham Shirt & Knit Tie


“This is the perfect outfit for a day that I need to look ‘dressed-up’ but leaning more on the casual side.

Whether it’s a presentation for school or going out for a summer night in the city.”

Bonus Tip: Gagan nails an updated fit. Slim, not skinny.

Bonus Tip II: If this picture were shot in black & white, with no context, you’d have a hard time telling what decade it was shot. That is timeless style.


Royal Cotton Trouser

Sky Blue Broadcloth Shirt

3. Chucks & Wayfarers



“Nothing says ‘just kicking it’ quite like a pair of white chuck taylor’s and a baseball jacket.”

Bonus Tip: If you’re a style conscious student, you need some good laid-back casual looks like this. You don’t want to be the try-hard kid in class wearing ties and lace-ups all the time (although that’s probably better than hoodies and runners all the time).

  • Blue varsity jacket by Brooks Brothers ·
  • Blue plaid shirt Handmade ·
  • Grey chinos by J. Crew ·
  • White sneakers by Converse ·
  • Wayfarer sunglasses by Ray-Ban

4. Weejuns & “Go to Hell” Chinos

“I had no idea what prep style was until a couple of years ago, and now it’s the primary influence on my look.

I’m a big fan of colorful ‘go to hell’ pants – just have to remember to keep everything else simple and relatively neutral. Although you can still have a little fun with a nautical themed belt.”

Bonus Tip: Because I know I’m going to get plenty of emails about this; “go-to-hell” is a popular phrase among prep enthusiats in reference to the in-your-face hue of brightly colored garments (most typically cotton pants in chino or corduroy).

  • Red/ blue bracelet by Kiel James Patrick ·
  • Burgundy penny loafers by Bass ·
  • Nantucket red pants by Tommy Hilfiger ·
  • Navy knit tie by J.Crew

5. Aviators & “GTH” Turban


“Four words: Go-To-Hell Turban.”

  • Navy cotton blazer by H&M ·
  • White shirt by Calvin Klein ·
  • Navy pin dot tie by J. Crew ·
  • Sterling Silver tie bar by Tiffany & Co. ·
  • Brown leather braided belt by Lands End ·
  • Indigo jeans by Uniqlo ·
  • Burgundy penny loafers by Bass ·
  • Aviator shades by Ralph Lauren

Thanks for reading and special thanks to Gagan for participating!

Yours in style,

Dan Trepanier


Photography by Alex Crawford.