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.

      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.

      • Parm Singh

        kya baat aa 22ji, I wear red turban with navy blazer some times. Just curious to know story behind “GHT”?

      • Kate Garcia

        who can tell me how old is the man?

      • sat

        Oye Balle Balle! Look dashing..way to go! For those who don’t understand, the beard and the pug(turban) were a sign of dignified prepy style of yore in classical India. If 400-800 years back you had to be preppy you would sport a neat Turban and a beard – you did not have to be a sage or a religious guy (to address someone talking about the nun in a mini) to do that. With the british influence that died down a lot. At the end of the day a pug(turban) is a hat and you guys should try it – it’s way cool. Gagan, it would be nice if you could put a madras turban on for us – that would be dashing! Good luck!

        • Preeti

          Yes, he does look dashing, but it’s not a hat. He doesn’t wear a madras turban because he is a Sikh.

        • Gagan

          Not sure about that, you can’t really say preppy style existed in India 400 years ago when it really started out in North America in the 1950’s. Most of the people wearing turbans in India back then were royalty or elites of society.

          Also, the turban is not a hat and most people would find a statement like that offensive, I don’t put it on everyday like one… I tie it everyday and it is way different from a hat.

          The madras turban sounds like a cool idea, maybe I’ll explore it further.

          • Sat

            On the dot, preppy style did originate in America in the 50’s and by definition one had to be a WASP with a typically a nice crop of hair and no turban. However, the term has evolved and is very inclusive and broad now. Preppy can also be used as an adjective or verb to define the spirit of being Preppy at any period of time in the history of Mankind. Preppy is just as much about intellect, attitude and how you feel as it is about dress.

            Now the turbans in the Indian Sub continent were/are the head gear of choice worn not just by the elites or royalty or a religious group- it was the head gear of most people. Different classes of people wore it differently and that distinguished one from the other. Not very different from hats in Europe where they were just as much a sign of respect and social class. Just as in Europe, where hats evolved and eventually became obsolete, only to be worn on very formal occasions – in India, most people do not wear turbans anymore. People who wear Turbans are either rustic from poorer sections of society or some who wear it on formal occasions, some royals occasionally or the Sikhs for whom it is a religious symbol (who also have many different ways of tying it).

            Indians and Sikhs by and large are very liberal and will not find comparing a turban to a hat offensive. But I’m sure there will be some who will and they probably will find it offensive that our beard is tied tight and not let loose as they wants us to. It would be like one of the traditional Preppy WASPs finding it offensive that one can be preppy with a turban on. To those I might have offended, I apologize before I am put on a guillotine! But just as my fore fathers wore the Turban religiously I still believe it was/is their/our head gear and essentially like a hat traditionally in Europe.

            Anyway, it is in the inclusive, liberal preppy spirit that the turban looks very cool and very much preppy! Good luck with the Madras Turban, I am looking forward to it.

          • Mitchell Harper

            Gagan my name is Mitchell Harper and I work for the Sunday Tribune newspaper in South Africa. We would really like to do an interview or story on you. Is it possible for me to get your email or telephone number.
            Could you please let me know as soon as possible

          • Mitchell Harper

            Gagan my name is Mitchell Harper and I work for the Sunday Tribune newspaper in South Africa. We would really like to do an interview or story on you. Is it possible for me to get your email or telephone number.
            Could you please let me know as soon as possible my email address is mitchell.harper@inl.co.za
            Thanks man
            Mitchell Harper

            Reporter – Sunday Tribune
            031 – 308 2331
            031 – 308 2357 (fax)

      • Connor

        where did you get the pocket square in look five?
        By the way the pocket square was a nice touch to bring the look together.

        • Gagan

          It’s actually a fabric swatch.

      • daniel shin

        any suggestions for woven/knit ties?


        • Gagan

          JCrew, J Press, Rugby, Uniqlo… even vintage stores. Almost everyone has them… just depends on the price you want to pay.

      • Raj

        Also he is wearing the same watch in every getup. My guess is its a Tag Heuer Carrera. Just goes to show that even one good watch is such a superb investment.

      • Raj

        Fantastic post! I particularly liked the baseball jacket look. A jacket like that will be a real asset to any wardrobe. Gagan you rock!

      • fan

        wow townsend is a fantastic photographer! great pictures and great post!

      • Norwegian

        Love your style, Veer! Diggin’ the way your dastar complements the rest of your outfit. It really makes you stand out.

        How do you choose the color of your dastar according to the rest of your outfit? Do you buy the clothes first and then a matching dastar? Or do you have some basic color for your dastars and just see what goes along with certain outfits?

        • Gagan

          Depends really, I have the basic colors but if there is something I want to match perfect… you need the clothes first and the turban second.

      • B S Sage

        Oye , SARDAR , Kar ditti Sardara wali gall, Koi akal di gall vi kareya kar.. . . . . .

        • Anon

          Read some history, man. Then come back and talk.

      • anonymous

        awesome post-townsend is a great photographer as well!

      • Anon

        You cannot have your cake and eat it too, the turban and beard cancel everything he is attempting to portray. It’s like a nun in a figgin’ miniskirt.

        • Gagan

          Oh, I didn’t know prep style was exclusive to certain types of people. What should I be wearing?

        • Manuella

          Boo…he looks good. Get over it.

          • Gagan

            Thank you Manuella.

        • anonymous

          what exactly do you think he should be portrayed as? some old school religious man?? he’s showing off his style not his turban.

      • Mike Terbenzdurti

        His style is phenom…

      • Greg

        Love the espadrilles! I need to pick up a pair for summer, they’re like the new boat shoe.

        Be Dapper Blog

      • Sindre

        I like the livestrong wristband on look 3. Nice detail.

      • Richard

        I never seem to get the fit of Jeans right. What type of fit is that in his last look? Looks like what SB wears too, i want something neither skinny nor loose.


        • Gagan

          If you live in/around NYC… get the slimmest fit of jeans Uniqlo has — a great alternative is JCrew’s 484 Slim fit, looks the same and available anywhere. Hope that helps!


      • Anonymous

        He is yummy! Is he single?

        • Anon Reply! :-O

          He is. DM him on twitter – @gdsingh.

      • Daniel

        Fantastic post! Affordable wears, and he wear them well. i especially like the 1st, 2nd, and 5th looks – the pant length is perfect: well-tailered without being a victim of fashion. Like you said, timeless. It also slims him down by providing a coherent line.

        And I agree with everyone, the turban in that last post is brilliant – as are all the ties!

        I’d love to see a future post featuring Gagan

        • Daniel

          Oh and the pocket square in the 5th look? Perfect.

      • dre

        Gagan, good looks brother. This post is unique because Gagan is unlike the typical prep thinking individual; also, he wears goods that are relatively accessible. Excellent job. I love the turbans. Truly your own, Gagan.

      • Brian E.

        Great updated “prep” style. I appreciate the accessibility of the clothing Mr. Singh is rocking. The GTH turban is too perfect.

      • paul fredrick

        Just got me some “go to hell” chinos. Awesome article loved it

      • VB

        Seriously, by far the most stylin dude you have featured SB. So bad ass. Dude is making reconsider my stance on espadrilles.


      • Robin

        Mr. Singh is a BOSS

        • Evan


      • Anonymouse

        The full body shot in #5 is one of the most badass pics I have ever seen.

      • Maurice

        Great post. The pink turban looks is cool. Somehow the baseball jacket and the turban seems a bit incongruous.

      • ChottuSingh


        All I can say is “way to go Singh”. Keep doing it big. Just tell all the fellow bloggers on here which Sikh you know really inspired the pink turban. :)

      • Random Cool

        5 stars for Gagan!
        He’s KILLING you on your on blog fellow!

        • Anonymous

          Now, now, let’s not get ahead of ourselves here.

      • Stephen

        Not only do I like all these looks (especially the H&M blazer), but it’s great how affordable they all are! It just goes to show you don’t have to spend a lot of money to be stylish.


      • Emanuel Iuhas

        Like , like , like !
        The ties and the belts!
        With all my respect for you and for Gagan , is the best-dressed man with turban and barb I ever seen!
        Congrats to you , to him !
        Thank you for all you give to us!

        Emanuel Iuhas
        Visual Merchandiser/Fashion blogger

      • Christopher Milan

        Gagan does it again, good sir I love your style and to me the turbans add extra flare to the looks. Style at its best


        Christopher Duwayne Milan

      • John Ryan

        This guy is the man – classic looks that he wears effortlessly. That turban if fierce, too!

      • Dillon

        As a college student, i want to thank Gagan – his looks are not only stylish but affordable. I have a difficult time extracting inspiration from some of the more affluent pieces.

        i caught the SB daily “preview” of Gagan and couldn’t be happier with the end results.

        nice work.

      • Arron

        My favorite post so far.. What kind of shoes are those in the first look?

        • Gagan

          They are just normal espadrilles, bought them when I went to Argentina.

      • Filipe Costa

        Great looks ;) I love his ties.


      • Bosun

        Absolutely love his style, especially the fact that he can wear espadrilles without looking like a dweeb (unlike most wearer here in England)

        Lovely post



        Great post! I share a lot of Gagan’s thoughts on style. Also, I want to compliment his watch. I have an identical Tag Carrera, and it is definitely one of my favorite timepieces.

        Great work as usual from the Style Blogger team…things just keep getting better.

        Stay Fresh,


        • Gagan

          I agree, it is my favorite.

      • Keaton

        Gagan or Dan,

        Great looks! Quick question: To get the pants to fit slender in at the bottom of the leg, do you get them tapered so that they fit close to the calf when they are rolled at the ankle? I have a hard time getting that look right. Thanks for any help you can give.

        • Gagan

          Those jeans are just from Uniqlo, the slimmest fit they have. As for the rest, I got them tapered, the tailor should know what to do.

      • Vinogram

        Don’t crop at the joints, Townsend!
        Otherwise brilliant.

      • mcr

        Awesome Post, All the looks are GREAT A+…This is why I check back daily on this blog, keep up the good work Dan, SB, and Gagan. Love the LANDS END belt, been looking for one just like that for awhile.

        Ps. Gagan what is your height?, are those Uniqlo jeans tailored?

        • Gagan

          The cool thing about jeans @ Uniqlo is they tailor the inseam for you for free so that is 30.

      • Vik

        LOL @ GTH turban!

      • T. Zagraniski

        As a military man with about 3/8″ of hair on my head, I must also express my utmost respect and admiration for the “go-to-hell” turban. That’s completely awesome.

        This is a GREAT post, Dan. Thanks.

        – TLZ

      • Rich

        I almost spit out my drink when I scrolled down to the GTH Turban. Killer looks!

      • alan m.

        Yeah awesome stuff. Gagan knows style. Nice shots Townsend, a jack of all trades. keep em coming SB.

      • Matt

        Fcking LOVE the GTH Turban!

      • Art

        Wow. That turban clashes and complements at the same time. Something about a Sikh dressed in western prep makes me realize this is why I love America. Loving it.


      • N

        Best thing TSB could ever do is feature this guy! Looking good Gagan!

      • TO

        The “gth” turban is one of the sickest things I have ever seen! Gagan has a way of dressing in a familiar way without it seeming (at all) cliché…well done sir