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, Oxford Shirt, Dark Straight 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.”

Blazer by H&M. Shirt by JCrew. Jeans by Uniqlo. Espadrilles from Argentina. Bracelet by Kiel James Patrick. Sunglasses by Ray Ban. Belt by Lands End.

2. Silk Knit Tie, Navy Chinos, Mini Check Shirt, Woven Belt

“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.

Shirt by Rugby RL. Tie by JCrew. Pants by H&M. Espadrilles from Argentina. Bracelet by Kiel James Patrick. Belt by Lands End.

3. Baseball Jacket, Chuck Taylors, 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).

Jacket by Brooks Brothers. Custom made shirt. Chinos by JCrew. Converse Chuck Taylors. Sunglasses by Ray Ban. Belt by H&M.

4. Weejun Penny Loafs, “Go to Hell” Chinos, O-Ring Critter belt

“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).

Shirt by Rugby RL. Tie by JCrew. Pants by Tommy Hilfiger. Shoes by Bass Weejuns. Bracelet by Kiel James Patrick.

5. Pindot tie, Aviator Shades, GTH Turban

“Four words: Go-To-Hell Turban.”

Blazer by H&M. Shirt by Calvin Klein. Tie by JCrew. Tie bar by Tiffany & Co. Belt by Lands End. Jeans by Uniqlo. Shoes by Bass Weejun. Aviator hades by Ralph Lauren.

Thanks, as always, for reading – and special thanks to Gagan for participating!

Plenty more awesome features to come.

Yours in style,

SB

Photography by Townsend Smith. As usual you can find more looks/shots in our Lookbook.