Unfortunate Fashion Choices Of Decades Past » VSB

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Unfortunate Fashion Choices Of Decades Past

Damon Dash, Roselyn Sanchez and Cam’ron attend the spring opening of Sky Terrace at Ian Schrager’s Hudson Hotel May 20, 2003, in New York City. (Stephen Chernin/Getty Images)


It’s the early aughts in NYC. A young East African girl (by way of Canada) is preparing for her sophomore year of high school in the North Bronx. She had just spent the summer with her family in France, and just KNEW she was ready to be fresh to death with her back-to-school outfit.

At long last, the first day of school came around, and she stepped confidently off of her Bedford Park Boulevard stop, onto Jerome Avenue, and strolled on to campus…wearing yellow stretch camo pants, black ups*, a denim jacket, oversized hoops, and waist length straightback cornrows.

Now, I don’t know this poor soul, but rumor has it that she has since burned every single piece of evidence that this outfit ever existed – save for one photo that her mother is keeping in her photo album under close watch, presumably for blackmail reasons.

While this a truly harrowing tale, this completely random girl wasn’t alone in this tragic era of “urban fashion.” The late 90s and early 00s** were chock full of disastrous fashion choices. No one was safe from matching their laces with their belt, or wearing a blue and orange jersey dress because the Knicks are your favorite team.***

1. The Cropped Down Jacket


For when you’re cold, but your abs are on fleek. The entire Baby Phat Era was just a dark time for us all. God bless Kimora for keeping hope alive.

2. Name Jewelry


I had a friend who had a huge crush on a girl in high school, and wanted to let her know by buying her a gift for her birthday. He saved his coins and walked to the jeweler off of Mosholu Parkway to get her name on a chain with white gold plates. The week before her birthday he went to go pick it up… and the chain said “Keisha.”

Her name was “Keshia.” $200 down the drain.

I wonder if he ever ended up dating a girl named Keisha.

3. Ridiculously Baggy Clothing (especially on skinny men)


This one will never fail to befuddle me. I mean, baggy clothes were silly in general, but slender dudes were really out there in their older brother’s hand-me-downs just drowning in fabrics like that was the wave. While I think we’ve overcorrected in recent days with the skinny jeans – I am quite happy that “shorts that go down to your ankles” are no longer a thing.

I could go on forever – Avirex flight jackets, NBA jeans, kitten heels –  but I try not to insult the sartorial choices of folks who have done extended bids in maximum security prisons.

Please feel free to litter the comments section with your tragic outfit decisions – I know at least one of you guys was overcommitted to Coach accessories, or walked around with a toothbrush to prevent your white kicks from scuffing. This is a safe space!

Well, not really. But know that we will roast with love.

*Air Force Ones for the uninitiated

**Also, the present-day Bronx

***Whoever this poor girl is, I hope she has found some fashion sense. But she probably just thinks that crop tops are year-round attire.

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Shamira Ibrahim

Shamira is a twentysomething New Yorker who likes all things Dipset. You can join her in waxing poetically about chicken, Cam'ron, and gentrification (gotta have some balance) under the influence of varying amounts of brown liquor at her semi-monthly blog, shamspam.tumblr.com

  • Damon Young

    Don’t forget the race car jackets. I had three of them.

    • DG

      Them NASCAR joint were everywhere…truly everywhere. I don’t think I’ve ever seen a more ubiquitous fashion trend than that one.

    • Dougie

      DAMMIT! I had a yellow M&Ms and a skittles one. FIRE! lol

    • Sigma_Since 93

      Don’t you know how many White tears this created???? There were sooo many country boys that were tight with the brothas repping their favorite driver.

      • Asiyah

        This might be what unites the races

    • miss t-lee

      These were so bad…lol

    • You can still wear these in the south.

      • Lea Thrace

        No. No you cannot. Do not spread these lies!

        • PhlyyPhree

          It’s not a lie if its true.

      • No, Malik.

        • Well not The Rainbow Warrior. You get a Dale Earnhardt one and stroll around in it in South Carolina and even the cops will give you some [white equivalent of dap here].

          • You speak with a forked tongue, Malik. There’s no manner of Dale Earnhardt clothing that will save you from a cop induced beat down or harassment. That’s like saying a Yankee cap will make the NYPD leave you alone.

            • I’m not saying it’ll save you. I’m saying if a white man sees you as a NASCAR fan in the south they’ll give you an affirmation head nod. Same thing happened when I was in Georgia and I have a Braves hat.

              • To be fair the Braves have the entire region locked up fandom wise.

      • PhlyyPhree

        I still wear these outside the south. Iont even care

        • aww, you’re adorable (^_^)

          • PhlyyPhree

            Why thank youuuu

        • miss t-lee

          You wasn’t playing…lol!

          • PhlyyPhree

            Wasn’t. I love(d) that jacket. I don’t wear it as often anymore, but I still have it within easy reach

            • miss t-lee

              I respect it.

        • You’re a Howard Alum?

          • PhlyyPhree


        • Nick Peters

          Crown Royal though?

          • PhlyyPhree

            Better than skittles.
            Besides, this was at tailgate. The Ques gave me allllll the free chicken.

        • KB

          This picture might be the next entry for “the blackest thing we’ve seen this week”. You got a crown royal jacket, holding a bottle of ciroc while, attending Howard’s homecoming. That’s the trifecta right there. No one will EVAH question your blackness. You’re rockin it tho

          • PhlyyPhree

            Lmaooooooo. Thanks but Nah. I’d need an actual bottle of Crown, same size of course, while rocking the Crown jacket to make it. I tried it though.

        • TeeChantel

          Yassssss! To the jacket, the scarf and to the hair curl on the side! :-)

          • PhlyyPhree

            LMAO. My hair wouldn’t do right, but of course I was drunk enough not to care.

            • TeeChantel

              Nah, you good. Your hair was cute.

            • QuirlyGirly

              Nah you looked good..LOL at the big bottle of Ciroc though..

              • PhlyyPhree

                Lol. Thanks.
                And that was like the 2nd or 3rd one of those bottles that day. I was giving out shots because sharing is caring and also, I cared about my liver.

      • miss t-lee


      • Ninja where?!??!!

    • I had a Valvoline one!

    • KayMac

      I’m still seeing Black folks around here wearing NASCAR jackets..I live in Arkansas.

    • KB

      My senior year of high school (foe tha 99 and 2000) I had a red hot wheels one that I bought. Man you couldn’t tell me ish. Spent my entire paycheck getting it. couldn’t eat lunch for a week but I was fresh ta def tho

      • Lea Thrace

        Did you do high school in Cport?

        • KB

          I didn’t but my family legacy is deep at Beach High School. We’re at the 3rd generation now. I was born there though.

  • DG

    I went through a brief period of doing the one pant leg up (a ‘la LL)…usually for my sweatpants. I didn’t think I was hard or anything…I just liked the look. A questionable fashion choice on its own, yes…but made worse when you have lil’ chicken legs like I do…smh

    • I’ve been there, bruh. Maybe it was a CSRA thing.

      • DG

        Yeah, folk…you might be right.
        Things getting back to normal down your way yet?

        • Yeah, a bulk of the damage in the low country is in Summerville and John’s Island. It’s weird seeing FEMA all over the place. My assistant is in the National Guard and he just got back from a week in Conway and Georgetown. Columbia and Sumter are getting back on their feet slowly but it may be awhile before Kingstree is back.

          South Carolina has had a rough year, man.

          • DG

            Tell me about it…it was surreal watching it on the news up here…seeing places I used to frequent underwater. It was disturbing.

  • Brandon Allen
    • KayMac

      I still have my name plate belt as a reminder of goofy I looked and to never do it again…

      • QuirlyGirly

        I love my name belt.

        Heck I could have a name chain or name earrings. Don’t take my name belt too!

    • miss t-lee

      Mall kiosk fashion at its best.

    • Pinks

      I just got rid of my Pinky name belt the other day. It hurt. It hurt bad.

  • Dougie

    I saw a white girl on the train today with a flight jacket and thought about how poor our fashion choices were in the late 90s/early 2000s.

    yes. I saw a white girl with a flight jacket on the train. Today. 10/23/15.

    • Question

      The repeat. And date confirmation. Yessir.

  • Personal sins:

    1. Wearing wave caps under ball caps.
    2. Silver/Faux platinum crucifixes
    3. Pajama pants to class
    4. Nike or Adidas sandals with socks

    Sham, as for the Cropped Down Jacket the chicks in Chucktown used rock them with boots with the fur that look like something a Inuit hoodrat would wear.

    • 909girl601world

      An Inuit hoodrat? I just literally screamed in this here dignified office space I currently occupy! Bwahahahahahahahahaha!!!!

    • Asiyah

      Pajama pants to class! I had a 7:25 a.m. class. You betcha I’m going to just brush my teeth, take a shower, and put on some pajama pants. It’s too early to think of outfit choices.

      • Sigma_Since 93

        What happened to laying you clothes out the night before???

        • Asiyah

          I’m a moody person, so the clothes I thought I would wear at 11:00 p.m. when I’m going to sleep wouldn’t work at 5:30 a.m. when I wake up lol

        • Most days for me in college were jeans and t-shirts.

      • PDL – Cape Girl

        I wore a pajama jumpsuit to work once (Lawd help me…lol), I went home midday and changed. I dunno, it seemed like a good idea when I left my apartment. I had on blue flats with it.

        I’m cackling. Young and dumb.

        • Asiyah

          Young and full of hubris! I miss that lol

          • PDL – Cape Girl

            Mmm hmm, and didn’t know a dern thing…LOL

    • uNk

      This isnt going anywere LOL ppl still rock this faithfully

      • Sigma_Since 93

        Sandals period with socks! I’ll give a pass to any athlete that is taking off spikes and putting on sandals but dasit!

        • QuirlyGirly

          I wish I could upvote this 10 more times. Please, Please, PLEASE stop with the sandals and the socks. Why won’t this trend die like the jheri curl

        • black-a-rican

          I saw someone wearing that in Europe once… He was from Atlanta.

      • Lea Thrace

        *sigh* my brother. White socks too! Ugh!

    • miss t-lee

      Inuit hoodrat?
      Lemme go lay down…lol

    • Superstrings

      The Cali dudes wore house shoes (the corduroy joints) with socks

      • kid video

        Don’t forget the hair rollers:)

        • Superstrings

          And the braided goatee like Dub C

    • BrownGirlGoneBourbon

      #3. I am so very, very sorry about #3. I thought I was cute, cotdamnit! Nobody told me! Nobody loved me enough to say a word…

    • DreDre

      tbh I think number 4 is acceptable, but only if you’re college-aged and the struggle is real. But if you are outta school in your late 20s and 30s and u think this is acceptable IN PUBLIC, then bruh we gotta talk

  • pls

    and just wth is wrong with bamboos and name plates?! I’d rather wear my gold jewelry than matchy matchy costume jewelry.

    I guess I followed the trend of having a belt from the beauty supply store in every color to match my kicks.

  • Courtney Wheeler

    I’m from Jersey..and as bougie as they come (Thanks for clothing representation VSB)..But I rock name jewlery…all day everyday.
    But nothing says “I don’t go to church and I’m behind in child support payments” than this stupid trend right here.

    • Lea Thrace

      This aint what Jesus died for…

    • miss t-lee

      The Jesus piece and chain!

      • Courtney Wheeler

        I’m trying to remember what rapper made this a thing. Should we blame Camron?…50 cent? Jadakiss?

        • miss t-lee

          Ha! I don’t quite remember.

        • kid video


          • Courtney Wheeler

            Okay…good point..and Coogi sweaters… :(

          • QuirlyGirly

            I think it was Biggie. At least he started rapping about his Jesus piece

        • pls

          kanye made the face piece popular. his own face as jesus and these fools fell in line.

        • CamCamtheGreat


    • Leigh

      “But nothing says “I don’t go to church and I’m behind in child support payments” than this stupid trend right here”


    • Shema

      I spit my coffee out at work, but that is the truth….LOL

  • I watched You Got Served this summer (don’t judge me, Netlfix was advertising it on their homepage. Who am I to say no?). It had been a while since I’d seen it, and I’d forgotten that the early ’00s was all about super baggy clothes. The entire movie is these 5’5″ men swimming in their clothes. Oh, and Omarion with cornrows.

    For my part, I did love me some overalls. I owned a ton of bodysuits for that reason. We ain’t have Timbs money growing up, tho, so I would rock the overalls with regular construction boot. This was the height of the Biggie era. (I own actual Timbs now because I can afford ’em.)

    • Asiyah

      Overalls! I can’t believe I wore those lol

      • Nor I! But imagine my surprise when I saw women rocking them last year. I was unprepepared.

      • miss t-lee

        OMG. Yes. Had a few pairs.

    • [Insert Creative Name Here]

      Man, lissen! I used to wear the h$ll out of some overalls. And I do NOT regret it in the least. One buckle loose too. And yes, I had Timbs of all colors (ex-BF had money for unstated reasons). You couldn’t tell me nuffin!

      • Heh. “For unstated reasons.”

    • miss t-lee

      We would just wear em with some steel toes…lol

      • Ohhhh. Steel toes! Man, I completely forgot about those.

        • miss t-lee

          Body suit, overalls, steel toes.
          Killin’ it…lol

          • Couldn’t tell nobody NOTHIN’!

            • miss t-lee


    • QuirlyGirly

      Bodysuits was the best. Surprised they not making a comeback.

  • cakes_and_pies

    You can add bedazzled du-rags and sunglasses with a rhinestones in the corner.

  • YeaSoh

    Velour Suits… smh

    • Juicy Couture had that on LOCK.

      • camilleblu

        juicy across the azz for the win…

        • Sigma_Since 93

          Pink is running a close second place

    • TeeChantel

      I loved my velour suit.

    • miss t-lee

      I had a lavender one.

    • Brandon Allen

      I rocked mine with a velour Kangol because I thought I was doing it.

      • TeeChantel

        Damn, Kangol.
        I had a red Kangol and loved it.
        I thought I was the girl out of the Sean Paul video lol.

        • MissRae

          Yass! I had a white one and a pink bucket style Kangol. This brought back memories…

          • TeeChantel

            Girl, too many memories.

    • uNk

      How about those Short sleeve/Shorts Valour suits for the fellas with some k swisses on LOL

      • YeaSoh

        Lol K Swiss smh

    • Dougie

      wait… velour suits aren’t still in style???

    • I used to want a velour suit TOO BAD. I blame hip-hop.

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