Prep Etiquette: Classic Tommy Hilfiger General Style 58 Comments

Trav : I’ve always been intrigued by the classic prep-and ivy-style when it is done effortlessly. RL Polo has always reigned supreme with their classic polo and their creativity with colors. One brand that frequently goes unrecognized, however, is Tommy Hilfiger. I might get in trouble for this, but the Tommy Hilfiger of the  90s had some of the best designs I’ve ever laid eyes upon. Their shirts and polo’s were spectacular. Tommy of today still makes good products but they are definitely a lot more toned down. I don’t quite know when it started, but myself and Josh have been working up quite the collection of classic Tommy Hilfiger pieces. T’is the season for a nicely fitted, tucked-in polo shirt, and this brand definitely delivers. Many of us are old enough to remember the extreme hip-hop sportswear trend of the 90′s that milked Tommy Hilfiger for all it’s worth. After the trend was over the Tommy brand was forced to do some extreme remodeling and ended up with a more toned down, contemporary, modern look. Stay tuned to see more classic Tommy pieces here on StreetEtiquette. I must add that this is not an attempt to turn this into a trend, its just us once again highlighting some well done pieces.

Travis Gumbs, Street Etiquette, Vintage Tommy Hilfiger, Vintage Tommy, Florshiem Wingtips, Duckie Brown, Duckie, Duckie Brown Florshiem wingtips

Fit Details : Tommy Hilfiger polo shirt – Uniqlo pants- Ralph Lauren Belt-   Florsheim X Duckie Brown wingtips

The Tommy polo came at a very, very reasonable price. Like I said before, these items from the 90′s go virtually unrecognized as everyone springs for the classic Polo items. I of course had it tailored. That shirt is actually a size large. I normally wear medium but after i got the body and the sleeves taken in, it fits great. I also have a couple of mediums that had to be taken in. For me, it’s really important to get a perfect fit on a polo shirt. Loose sleeves and a boxy fit throws off the entire look, no matter how dope the polo is. The secret to getting stuff tailored at a bargain is buy cheap, but that goes without saying.

These shoes are one of my most favorite to date. I got them a couple months ago on ebay. The Duckie Brown collabration with Florsheim always delivers. The colors are always interesting and on point. I find that the paint of the edges tend to chip which is very unfortunate.

Florshiem shoes, Florshiem wingtips, Duckie, Duckie Brown Shoes, Duckie Brown wingtips, Duckie, Brown, Wingtips, Florshiem wing, Travis Gumbs, Street Etiquette, Etiquette bronx, Street Bronx, Bloggers style

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  • Lowhency "LoLo"

        posted on April 21 , 2010 :


  • Prêt à Porter P

        posted on April 21 , 2010 :

    Those shoes are incredible!! I love cobalt blue!

  • JLouie

        posted on April 21 , 2010 :

    I really like your polo! I recently found on old tommy hilfiger polo in my closet i’ve probably had since like 8th grade or longer. It was a little short but other than that, the fit was really nice. Its just a plain navy polo with light blue strip accent behind the buttons, but paired with some brown and blue gingham trousers and tan boat shoes, it was probably the most commented on outfit i’ve ever had. I’ve been on the lookout for boldly colored polos lately like the one josh had on a couple posts ago, and now yours. It’s tough to find ones with the vertical stripes, i like those alot.

  • [...] HERE to read the full article at Street [...]

  • Waraire Boswell

        posted on April 21 , 2010 :

    Simple is always best.
    This look is LA prep 1993.

    A great look for the squire of spring.


  • mr sekimachihato

        posted on April 21 , 2010 :

    i think i need arms like yours (errrm, muscles) to really pull-off a polo shirt the way you do.
    i like your uniqlo pants. there is a new word in japan now called “uni-kaburi” which means to bump into someone on the street wearing the same uniqlo clothes. i can see it happening not only in japan too one of these days…

  • Kadeem J.

        posted on April 21 , 2010 :

    Trav this look is tooo smooth man. You are stepping more and more out of the box…much respect man!

  • Ashley

        posted on April 21 , 2010 :

    i love this because it reminds me of more dapper carlton banks! and those shoes rock my socks off!

    i’m curious… what kind of camera do you guys use?

  • Vincent

        posted on April 21 , 2010 :

    I’m about to do a post JUST FOR you guys. I have some OOOLLDDD Tommy stuff from my big brother from the 80′s & early 90′s.

  • duzz

        posted on April 21 , 2010 :

    im just about to start hitting the gym on the reg, in order to get a polo to fit. dope outfit proportions are on point!. keep it up man.


        posted on April 21 , 2010 :

    Am lovit it ;)

  • Al_Bizzy

        posted on April 21 , 2010 :

    I’m definitely feeling ya’ll with this post, the mid-late ’90′s was definitely a great era. Ironically enough, I’ve recently been bringing back my old Nautica and Helly Hansen pieces. I’m sure ya’ll some of that stuff archived too. Bring em out-bring em out!

  • Aimee Piper

        posted on April 21 , 2010 :

    I think that a good tailor is the key to a fantastic wardrobe. …also? I’m enamored of your shoes – cheers.

  • mat ahoy

        posted on April 21 , 2010 :

    it’s safe to say, they are some of the best shoes i’ve ever seem. the colour is amazing. i just remember the jeans with a massive TOMMY down the leg

  • Angelo

        posted on April 21 , 2010 :

    Daimn, I need to work out more if I want to wear fitted shirts like that!

    I’ve been wondering though, looking at this blog I really dig you guys’ style, but colour-wise I think it won’t work for me being a white blonde guy (home-grown Dutchie!) Any tips for adaptation with different colour palettes?

  • Rashidi

        posted on April 21 , 2010 :

    Dope polo, dope fit. I have a few that I’ll be taking to the tailor soon. It’s hard to get the right fit off the rack. H&M, and Benjammin Bixby Polo’s are the only one’s that fit me well.

    Honor thy Tailor,


  • Marcus Troy

        posted on April 21 , 2010 :

    Amazing! I’ve always wanted that POLO (back in the day) The color blocked polo’s by Tommy were always hard to find. The tailored look is such a great look. Great Post!

  • Kristopher

        posted on April 21 , 2010 :

    Shoes are just crazy. Good fit, good colours, what more can be said?


        posted on April 21 , 2010 :

    A great much needed post myself and Travis have been both indulging in these bold symmetrical pieces from Tommy Hilfiger really attracted to the color palettes and detail. Ralph produces some great pieces but sometimes difficult to get because of all the attention on his vintage items especially on eBay , you would be lucky to come across such in a thrift store without someone already snatching that steal.

    Although Tommy had his great reign I feel like the brand lost it’s identification and started to follow suite on something that already existed solely because it was the ‘popular’ thing to do and they were running out of options. Now bought out by the same people own Calvin Klein – to me most of these pieces we have are a part of history.

  • E

        posted on April 21 , 2010 :

    Hi I love your style (!)

    I was wondering if you have any specific stores or sellers that you follow/ recommend on eBay ? Since it seems that you guys buy a bunch of your clothes on eBay.


  • Shen Dove Style

        posted on April 21 , 2010 :

    This is a great look! Your shoes really bring everything together nicely.

  • EugeneLulz

        posted on April 22 , 2010 :

    Damn, that polo is dope and fits perfectly. And the colors of the outfit are just stupendous.

    Info on that bag Travis is carrying?

  • EC

        posted on April 22 , 2010 :

    I agree, I remember 90′s Tommy/Nautica always had interesting color combination’s, Tommy especially in their Polos. Great post although I have to disagree with your preference of a tailored (tight) fit versus a looser look. I guess it just depends on individual style.

  • LOLA

        posted on April 22 , 2010 :

    This is so ironic because I was looking through some old family photos the other day and I noticed that my sister and I wore a lot of Tommy Hilfiger when we were younger! BTW, those shoes are ri-di-cu-lous! Haha

    -xoxo LOLA

  • kevykevykelvin

        posted on April 22 , 2010 :

    Very dope classic polo,i’ve always felt if you gonna wear apolo it has to be tight fit

  • Williams Jay

        posted on April 22 , 2010 :

    Great fit , I used to wear a lot of Tommy back in the day so it’s great to see you fellas transform it to your own standards and bring it back to life. This site is such a special thing I don’t think people realize.

  • TeoV

        posted on April 22 , 2010 :

    it was about that time , you had to make an entry on tommy hilfiger :-)
    I like … classic preppy style

  • Stephen

        posted on April 23 , 2010 :

    I really like the minute red accent on the collar of the polo. And those shoes and are indescribable.

    Long may your blog live.


  • Emily

        posted on April 23 , 2010 :

    Great outfit love the color palettes here!

  • Aaron White

        posted on April 23 , 2010 :

    Tommy would be considered so cool back in the day I remember where everyone had something from Tommy or Fila , its sad to see tommy especially die out the way it has , but great fit overall man

  • sssence

        posted on April 23 , 2010 :

    Man, the 90′s were some of my best days and I can remember when TH was 80% of my closet! Oh how things come back around. I really dig the colors on this piece, and with the shoes it makes the outfit very solid. I’m going to have to keep my eye out on ebay for some Duckie’s.

  • pinkess7

        posted on April 23 , 2010 :

    I love the color of the shoes, and how you rolled up the pants to highlight them. I am a female that likes structured looks with a lil pop. Hotness.

  • District Cut

        posted on April 23 , 2010 :

    In my opinion, Hilfiger was one of the greatest design labels back in the day. Over the past decade they have had a dry spell, but I think they are picking up momentum again. Like they’re new range with Macy’s

  • Abu Mansaray

        posted on April 24 , 2010 :

    That shirt is so classic. I don’t know about me liking Tommy Hilfiger that much over Ralph Lauren tho.

  • Oswaldo Sanchez

        posted on April 24 , 2010 :

    Extremely well put together outfit. I dig.

    The red accent. Subtle, yet without it the polo would lose its magic.

    The Ralph Lauren belt. Compliments the accent, yet stands on its own.

    The pants. Although being a different blue give the piece unity.

    The shoes. Maybe a bit too bottom heavy for me. I feel the eye immediately shifts down to look at them. They move the focus too much.

    Excellent post. I look forward to reading the next one. Keep up the good work.

  • yamina

        posted on April 24 , 2010 :

    your blog impressed me ! love it

  • lineag of influence

        posted on April 24 , 2010 :

    The shoes are amazing, that colour’s just fantastic. I can’t stop looking at them, must find a pair…


        posted on April 25 , 2010 :

    Love all outfit :) it’s great to see guys caring about fashion and have so much success with his combos! Amazing colours and those shoes.. to die for!

    beijo *

  • David W. Albert

        posted on April 26 , 2010 :

    My man I was about to say like wow with the TH, for a second I was going to say bold move then you said, I might get in trouble for this…” I was almost unsure that you realized the speculations were not in the air, but anyways on to what my point was. I could not agree with you more on this matter because for the simple fact that before the whole story came out about the respected designer and his company not being big supporters of Black and Hip Hop cultures. The brand was one of my favorites along with Nautica which I still feel goes under the radar as a well designed brand, but that is another topic. I may let you know that the pieces of theirs that were my favorite along with their short sleeve polos were thier long sleeve polos for the fall seasons. Where most of the time like you said there would be mounds of vibrant and well put together color cordinations. As well as the design quality being on point too. Oh and about the Duckie B collabs on the feet good choice bru and as far as the paint on the shoes chipping off just think when they are really broken in they will be proper with a pair of denim or khaki pants and some white or light blue shirt. Better yet with a cambri shirt this is like a in the long run type of fit I thinking bru. Haha Anyway man be easy and keep delivering fire.

  • Seth

        posted on April 26 , 2010 :

    Great post here gentleman you guys keep moving in a great direction

    I found this blog via Vogue Italia! congrats on that

  • SwanDiamondRose

        posted on April 26 , 2010 :

    oh boy. blue brogues. so nice! i’d love to see more colours of those. i just got another pair, more of a soft shoe, in white.

    just watched the Mickey Drexler interview you posted on Hypebeast. thank you so much. i really needed to hear information like this.

  • david

        posted on April 27 , 2010 :

    once they switched from the coat of arms to the flag i switched to polo in the 90′s…i use to buy the tommy t shirts with the coat of arms logo at the bottom and rock em in the summer wit hush puppies…clasic summertime chi

  • Anthony

        posted on April 27 , 2010 :

    i like that polo a lot!
    my only beef with the outfit is the blue pants with the blue shoes, it seems a little over done. nevertheless i love the shoes as its own piece

    Tav and JKISSi, ill be going to downtown nyc on sunday. do you guys have any suggestions for stores or specific thrift shops other than Uniqlo and Topman?

  • Kendriana

        posted on April 28 , 2010 :

    Great shoe!
    Are socks not the “cool” thing to rock anymore?

  • Chris Erwin

        posted on April 28 , 2010 :

    This shirt is dope. If knew then what I know now, I would have kept all of my tommy polos…oh well lol…and I need those shoes. Ive been addicted to wingtip shoes lately. I live in New Orleans and dudes aint really on those type of shoes…I think thats why I like them so much.

  • PeezoMTF

        posted on April 28 , 2010 :

    yo Trav if you stay in that gym you’re not gonna be able to fit a large anymore dude lol. Great post as always fellas!!

  • The Funky President

        posted on April 28 , 2010 :

    If you’re looking for a deal on Duckies, if you are in NYC, just saw some in the Century 21 flagship. Not the brogues, but the oxfords and loafers in some dope colors — blue, green, red, tan.

    I like how TH started out, as a modern, urban take on preppy style. Tommy ties were dope too. they had one print on the front, with the tail being another print.

    But the louder it became, the more I stayed away from it. I could deal with the small logo on the polos, but when the flag was all over the place, and the name TOMMY HILFIGER became too big and prominent on the clothes, it became more about the brand and less about the style. It was too gaudy and garish for my taste – like the Ed Hardy of its day. I think that, and oversaturation led to its decline. I actually like some of the Tommy stuff now, clean basics sans logo.

  • Trav

        posted on April 28 , 2010 :

    Lowhency “LoLo”: Thanks man

    Prêt à Porter P: thanks cobalt blue is definitely nice

    JLouie: Yeah man. We are on the same page. Its all about the vertical striped polo. That fit u mentioned sounds pretty dope>

    Waraire Boswell: u got it man!.. I really love what you do..i take a bow to your work…very inspirational.

    mr sekimachihato; ahaha thats really funny. We only have one Uniqlo here and as big as it is..i rarely see people in it unless im in soho.. but maybe that saying will reach its way down here lol

    Kadeem J.: Thanks once again bro…Just tryna keep it interesting

    Ashley: Thanks haha…its funny because Will was always the one who got the style attention, but Carlton did his thing when it came to prep. I shoot with a nikon d40 right now

    Vincent: ahhhh man…i’m seriously looking forward to seeing that!

    duzz: yeah man…the gym really helps when it come to getting the “polo fit”

    DELPHINE: Thanks!

    Al_Bizzy: you said it bro..all great brands of the 90s

    Aimee Piper: Thanks man..Yup!.. a good tailor is what separates your wardrobe from the rest.

    mat ahoy; haha!..yea man.. those jeans were pretty terrible lol

  • Donnie Brasco

        posted on April 29 , 2010 :

    OH MY GOD!!!!!! Its safe for black people to wear tommy again? I cant belive it. Tommy messed himsefl up after that whole “i dont make my clothes for the urban community(black people)” stuff in the 90′s. I remember sitting in class in like the 3rd grade decked out in tommy hill and feelin ill and errbody came at me like “why do you have that on” “hes a rasist” third grade mind you! I would say about a week later my mom threw out all my tommy hill gear and replaced it with gap and old navy because they were big in the 90′s too

  • vpm

        posted on April 29 , 2010 :

    What are your thoughts on wearing white undershirts with polos or v-neck sweaters? I don’t see it as much now-a-days as in the past.

  • Lioness

        posted on May 14 , 2010 :

    AAAAAAAAAAAAAAAAAArgh me like it! Both of you! Would you marry me? Think I am in love… :)

  • 20AKI

        posted on May 19 , 2010 :

    I just got here and I already must disagree with all you guys LOL! SERGIO TACCHINI polo’s have always had the best and most rare prints! The vintage ones are just classic. I just copped one brand new in the plastic from a seller in australia. We wear polo’s alot in Houston so we are always looking for something that will turn heads! RL Polo’s are hard to beat but SERGIO TACCHINI is King And @VPM a new white undershirt under a polo is a must!

  • Usher Goes Prep for London « The Purple Journal

        posted on June 9 , 2010 :

    [...] Usher signs autographs in London, he pulls out the plaid cardigan for a more  preppy look. See another take on this look below (via Street Etiquette): [...]

  • SWURDIN | tommy hilfiger brought his family

        posted on August 4 , 2010 :

    [...] a faux Hilfiger family to promote this new direction. Now I’m a big fan of the the flamboyant preppy and streetwear looks the brand is known for. But nowadays it just seems like a brand for that guy [...]

  • Sarosh Adil

        posted on November 12 , 2010 :

    Great look you have going. I too am a huge fan of polo shirts. I have a bunch of the newer Ralph Lauren custom-fit polos. A size small, though perfectly fit around the chest, is way too loose around the waist. I never thought of having them tailored though, so I am going to give that a try, should of thought of it sooner! Thanks for the great tips.

  • Nuridin Yoozy D'fhai

        posted on May 13 , 2011 :

    street etiquette …….no size

  • orbital

        posted on April 18 , 2012 :

    Please spell check. “Collabration” is spelled collaboration. We must keep online writing from ruining the english language.

  • Slim

        posted on March 26 , 2013 :

    Bro dat shirt sticky I still fuck wit Hilfiger despite the racist rumors he should bring the coat of arms logo back that’s when it was better than Polo and Nautica. Speaking of nautica they brought back they original boat logo