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Who Wore It Best? OshKosh B’Gloss Edition


Happy Friday! At the behest of our tech guru, Michael (who clearly only wants to do this because he thinks he'll win), we are having a Who Wore It Best? competition à la Us Weekly, based on our own #ThrowbackThursday Instagrams. The totally coincidental (!!!) theme? Overalls. The time? The early '90s. The style: various degrees of awesome.

Please designate your choice (again, this is Michael's idea) in the comments section with a #TeamNick, #TeamEmily, #TeamMichael, or #TeamAlessandra. (Sadly, Elizabeth was exempt from the competition on account of her not having any overall kiddie pics...she may have already won?)

The winner, of course, will receive the ever-lasting pride of victory, and (pending availability), an equally well-fitting pair of overalls they will be forced to wear next New York Fashion Week.

Let’s Talk About It! JOIN IN
  • mickharper


    • mickharper

      who down-votes a four-year-old? come on people, this isn't reddit.

      • Kate Barnett

        kid's got hungry eyes. #FutureEagleScout #TeamMichael

      • ITGAlessandra


  • Emily

    #teamalessandra - purely for the one-shoulder styling... (and the turtleneck/bob combo is pretty great too)!

  • Molly

    You are all so adorable....I can't handle this post. That being said, I'm going to go with #TeamEmily. The crossed arms, the stank face, the rose in the mouth, I mean it's unbeatable Xx

  • Kara Manos

    #teamalessandra for the chic one-shoulder styling and the cute bob

  • Nicole

    #TeamAlessandra :)

  • Jeremiah

    #TeamMichael !!!

  • Bankrupt


  • http://twitter.com/thelovelaceclub the lovelace club

    #TeamAlessandra all the way!

  • Jen


  • Ann

    Yo, this was really tough. But #TeamAlessandra, sorry!

  • Jill

    #teamalessandra - even that excellent photobomb can't take away from dem overalls

  • Sandra

    TeamNick!!! Definitely!!! But all of you are soooo cute!

  • LK

    Emily because apparently that photo was taken on my 14th birthday and I could probably dig up a photo from that day with a similarly amazing '90s outfit

  • Sandra

    ...and cool parents! :)

  • adrienn


  • Julián

    #TeamAlessandra And that chic, blunt haircut seals the deal.

  • Mai


  • katie6373

    #Teammichael for total crazy face and unique style of overalls.

  • loulou

    #teammichael. That picture is terrifying.

  • Belle Taylor

    It's just too good!

  • Sylvie

    TeamAlessandra! Saucy with overalls is truly impressive.

    • ITGAlessandra

      I'm blushing! I try. x

  • robyn

    #TeamAlessandra that hair! the turtleneck!

  • pamb

    They are all awesome (Happy family! Biting a rose! Crazy brother on the couch trying to get in the picture!) but the winner is Santa Baby. The reflection of the glass means it's still framed in the parents' home. The brother with one closed eye is so happy to be touching Santa. The overalls wearing is secondary to all of that kitsch!

    • mickharper

      i really enjoy your analysis. it's framed over my dad's washer/dryer. Which is actually an improvement over years above a toilet.

  • li


  • http://twitter.com/rqandrade_ Raquel Andrade

    #teamnick because he has the best parents, and a silly face!

  • anthisanthat

    (Dear God!)

  • Tasha Sumatra

    I love Emily's sass, but #teamalessondra wins out for sheer adorableness.

  • Anja Dreyer

    #TeamAlessandra <3

  • N

    Are you kidding?? #TeamMichael

  • Anna Stromberg

    TeamMichael, ofcourse!

  • Clementine

    #TeamMichael - that winkeye, Santa's big paw-like hands..straight out of a Coke ad.

  • Samantha

    I have to go #TeamEmily. The rose in her mouth makes it!

  • Me

    It has to be Michael:-)

  • Alison Bell

    I'm going to have to say Nick because that is the most heartwarmingly cheesy family photo I have EVER seen. XO

  • Paulina

    Hahaha you guys have a great sense of humour. It is really cool you show your pics from the childhood ;) you all were cuties :)


  • Elspbeth

    #TeamMichael Dem 'ralls

  • http://thecornerapartment.com/ Elizabeth @ TheCornerApartment

    Team Nick! A too-big polo under denim overalls... classic!


  • CFH

    #TeamMichael. What ARE those things??

  • ITGAlessandra

    <3 <3 <3

  • enemell

    I cannot tell you all how much I am freaking that these pictures were taken in the NINETIES. You were all babies! Wow. That said, I'm going #TeamEmily. Cute rose, plus the date in the corner gave me a thorough freakout.

  • Cha Cha


  • Lexi

    They're all super cute! My vote goes to Team Alessandra

  • Paola

    #teammichael.........though Alessandra your four year old self is adorable

  • sonaluna


  • lyd

    nick's parents look awesome. i love dad's who look like non-creepy jeff goldblums

  • http://twitter.com/beautypalette Kathy


  • Lauren

    On top of the photobomb, young Alessandra is carrying a paperback book to accompany her model moves. Smart and fierce?! Winner.

  • goodbadandfab

    Love, love, love!!!

    personal style and fashion musings of a LA fashion lawyer living life in the fab lane!

  • juliarose


  • cat


  • The Fashion Informer

    I'm abstaining from voting in this round (too hard to choose) but may I suggest for your next ITG competition, you guys post images of your worst-ever hair styles? (Cause who among us doesn't have some awful adolescent hair pics?) The winner could get some hair care products. Just a thought.

  • Hannah Kessel