22 Rome Street Style Looks to Copy and Paste (on Yourself)

The number one thing I remember about visiting Rome in college is that I was very concerned with what I’d wear, because I was told that Romans looked great, always, no matter how hot it got.

The number two thing I remember about visiting Rome (after the sights, of course — you gotta see the sights) was that there was something about the city that seemed to imbue its pedestrians with confidence and humor, which then translated to what they wore, no matter if I’d wear it or not. Maybe it’s because those who visit Rome seek beauty, so they bring beauty with them. Maybe it’s because when you look up and spin around you’re made dizzy by ancient grandeur. Maybe it’s because there were so many people from all over the world that to single out a city native would be unproductive — so what I did instead was single out interesting outfits.

The same musings came back as I clicked through the selection that Simon Chetrit shot for Man Repeller. That girl in the red-and-white tiered dress with the bike? (Note to self: find white flats.) She looks like she’s lived in Rome forever to me. So does that man in the pink blazer. (Another important shopping note.) If he’s not a born-and-bred Roman, maybe he just came over from men’s fashion week. Slide six, the girl in the ivory dress, see how she makes it look so easy? Is she a visitor from elsewhere who came in proud, her aesthetic established, and then used the Roman light as her final-touch accessory?

The answer isn’t so important, I suppose, when it’s the inspiration that’s the takeaway. Join me then, won’t you? Cue up the playlist below, hop aboard my Vespa and off we go on a Roman holiday.

Photos by Simon Chetrit; follow him on Instagram @simonzchetrit.

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  • Alison

    #6 is awesome. Summer is here!

  • isabela avelar

    couldn’t help falling in love with this playlist, AMAZING

  • Beth

    Wowow loved these looks! Super refreshing to see street style that isn’t NY or Paris. So romantic and breezy!

  • Camila Restrepo

    You forgot this song in your playlist, “Roma non fa la stupida stasera”! 😀

  • Ana Vla

    everyone obsesses about the ‘french wardrobe’ but seriously, italians are the ones that know what’s up.

  • Néo Bourgeois — Montecito

    Hate Rome, followed by prostitutes the whole time.

  • Stacey

    That was fun 😊 loved #2

  • spicyearlgrey

    the playlist is very much american checks out italy, not very the music of rome

  • Lately, I have been so inspired by Italian style. Discovering brands such as The Attico and Massimo Georgette.
    I am traveling to Milan in two weeks, so this was definitely the street style inspiration I needed 🙂

  • Spence

    Loooooove that you included people with non-traditional street style; especially the older men. So refreshing. Young, thin fashionistas aren’t the only ones with style on lock down! Thanks for showing that. 🙂

  • Spence

    Looooooove that you showed people with non-traditional street style, especially the older men. It’s not only the young, thin fashionistas who have style on lock. Thanks for showing that! Very refreshing. 🙂

    • Simon Chetrit

      It’s always what I aim to do, thanks. 🙂

  • Is it weird that I prefer all the male looks? Haha!


    • Simon Chetrit

      The guys really brought it on this one, gotta say.

  • Anna Fiore

    Help! Where to find pants like #15?? I’ve always been a dress/skirt person, but I want to broaden my horizons.

  • Cattleya

    “Week-end à Rome” should be in this playlist too! Fromage Étienne Daho and sang by Vanessa Paradis (on nouvelle vague record).

  • Daeyz

    Love the looks!


  • Bambi loves Rose

    So agree! Also should have an eye on Tiflis Streetstyle.

  • Bambi loves Rose

    Edit: Is the girl on pic 22 Jennifer Love Hewitt? 🙂

  • Mallory

    I’m a college student in Rome at the moment, I’m constantly asking myself “does this look too American?” I’m trying to balance my own personal style and the local style; it has been difficult. I’m also in awe of the layers and pants the people are wearing here. I can’t stop sweating!!

  • Leah

    Italian men… just have it

  • Ron

    Rome, thou art a whole world, it is true, and yet without love this

    World would not be the world, Rome would cease to be Rome…

  • Rob

    Rome, thou art a whole world, it is true, and yet without love this
    World would not be the world, Rome would cease to be Rome…