I Tried 6 Street Style Looks to See If I Could Pull Them Off

I’ve said it before and I’ll say it again: Street style is a veritable gumball machine’s worth of viable outfit inspiration. Okay, I’ve never actually said that out loud, but I’ve thought it many times and I’ll tell you why: Unlike a runway or a presentation that serves up Big Thoughts on a hard-to-reach platter that may or may not take six months to fully absorb (not to mention buy), street style makes it easy. All it takes is the turn of a silver knob, or the click of a mouse on a slideshow, and plop. A colorful, bite-sized ball of fun falls right into your hand, and all you have to do is toss it into your mouth and chew.

The digestible nature of street style stems from the fact that it’s composed of trends in broken-down form — filtered from runway to buyer to retail to customer to closet, a process in which the question of how the heck do I actually wear that? receives a bounty of different answers and interpretations.

Every fashion week, I keep a note in my phone wherein I type out ensemble ideas gleaned straight from the concrete. Eager to test-drive them myself, and inspired by Haley’s mirror selfie documentation of her own street style copycatting adventures last season, I decided to chronicle mine. Peep them below and let me know how I fared.

Look #1: A Leopard Statement Coat Homage

Tamu McPherson has one of the warmest smiles of any fashion week attendee, and I can testify to this fact since I have been the lucky recipient of it more times than I deserve. In exchange, I recreated my favorite of her looks from New York Fashion Week, a leopard statement coat/head-to-toe white/beret combo platter I love so much I also posted it to Man Repeller’s Instagram. I wear head-to-toe white outfits frequently, but this was my first time wearing a beret — I borrowed it from the MR fashion closet. Frankly, I’m not sure I pull it off, but the rest of the clothes felt like my birthday suit (i.e. utterly natural, could wear forever, TY for asking).

Look #2: A Donna Tartt Vibe

There was a lot about this outfit that landed it outside the bubble of my usual sartorial proclivities, from the oversized masculine tailoring to the lack of color. But something about Simon’s photo of actress Coco Baudelle channeling an intimidatingly chic Donna-Tartt-vibe haunted me in a good way. I was surprised by how much I fussed over the simple black suit and button down shirt, but I guess that’s what happens when you try to speak an unfamiliar style language (my native tongue is maximalism, and maximalism this was not.) I would probably never wear this again, only because it didn’t feel me, but it did feel extremely cool, so that was fun.

Look #3: A Transitional Weather Turkey Tux

I enjoyed this riff on the Canadian tuxedo stuffed with extra layers like a transitional weather turkey, and it was super easy to recreate. That being said, I wasn’t wowed by how I looked, only because I didn’t have the appropriate accents to spice it up, like the camo baseball cap and blue scarf. I’m going to keep thinking on how I can appropriate the bones of the ensemble (jeans + beige overcoat + jean jacket) and make it my own: perhaps a snazzy statement top instead of the black sweater, or different shoes.

Look #4: An “Everything But the Kitchen Sink” Situation

Vintage pants, Tory Burch sweater vest, J.Crew turtleneck, Trademark bag

This was definitely the most fun copycat attempt seeing as it definitely spoke to my “more is more” philosophy, and I happened to have the perfect maroon and orange sweater vest. The outfit spoke to me on a visceral level before I even realized the person in the photo was none other than MISS JAY OF AMERICA’S NEXT TOP MODEL FAME (!!!!!) — a revelation that Haley and Amelia pointed out. What an honor to be in the same side-by-side. I’m not sure if I would wear this again — it’s a bit much, even for me — but the process of putting it together reacquainted me with some neglected pieces in my wardrobe that I definitely plan to trot out in the coming months.

Look #5: A Head-to-Toe Sweats Opportunity

I will seize any opportunity to wear sweatpants and a sweatshirt and sneakers in tandem, which is why I bookmarked this particular ensemble. I liked the idea of elevating a full “sweat suit” look with a brightly colored jacket and matching cap. I don’t own anything orange (not on purpose), so I subbed in a millennial pink blazer. Somehow I ended up looking more like “Professor Umbridge at the gym” and less like an impeccably chic woman dabbling in athleisure, but man oh man was it comfy.

Look #6: A Dorky Dad + Eccentric Octogenarian Mashup

Of all the outfits, this is the one I ended up loving the most and will certainly wear again. The whole thing was me, top to bottom: non-athletic sneakers, jeans, beloved Edith Young T-shirt, statement coat, tiny rainbow bag and sparkly sunglasses — which, yes, are exactly the same pair as those sported by the woman I’m imitating, though mine were borrowed from the Man Repeller fashion closet. It was the perfect mix of dorky dad and eccentric octogenarian — one of my favorite personal style profiles. Now I just need to convince Haley to recreate the other outfit on the left and post with me mid-stride…

Street style photos by Simon Chetrit; follow him on Instagram @simonzchetrit. Selfies by Harling Ross. 

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  • Olivia Lauren Hawk Moore

    that Donna Tartt look is so good so so so good

  • Malene

    Loved the Harry Potter reference hahaha! You’re too cool, Harling.

  • vss

    I wanna see you in more “Everything but the kitchen sink” looks. Octogenarian Mashup was so good too.

  • Cynthia Schoonover

    I like all the looks.

  • Kate

    the sweatsuit under a blazer is actually a LEWK. I’m convinced I’ve tried everything already, but this has actually never occurred to me and is now my favorite.

  • Adrianna

    I wonder what impression people outside of NYC get when browsing street style blogs. Everyone I pass on my morning commute from Brooklyn to downtown Manhattan is wearing a variation of blue or black jeans and a black coat.

    • Nancy

      I always wonder where all the fashionable people hide! Everyone on my train is hidden is black coats and a stoic winter game-face. In warmer months people wear nice street clothes, but I’ve found that it’s usually nowhere NEAR as creative as manrepeller/street style (I’m not much more creative either).

      • Adrianna

        This is my first time with a longer commute (I used to live and work in the east village. Now I’m in park slope) and I quickly switched to sneakers and a backpack. I haven’t used purse since moving

      • Kelsi

        One word, four letters: SoHo
        Working at one of the lone non-profits in the ‘hood always has me feeling like a fish out of water. But the inspiration is tops!

    • JennyWren

      Ha, I live in the Midwest, so it was kind of funny to me that Harling would describe street style blogs as more attainable. If I tried any of these looks ’round here I’d probably get asked what medication I was on and why had I not taken it today. Then someone would bring me a casserole.

      • Adrianna

        I love Man Repeller, but the style section is becoming a bit of a parody of itself. Maybe I’m just old? (29) Honestly, most people in NYC look like they got a makeover on What Not to Wear.

      • nieceeray

        This comment made me actually LOL and I hate that acronym.

    • Lyric

      In Berlin it’s like 50% all black and 25% street style 25% mainstream trends

  • Kristina

    Harling, sis you never fail to SERVE LOOKS these are amazing!

  • Kristin

    A Transitional Weather Turkey Tux is my go-to Friday outfit (aka Denim Fridays, not quite as exciting as Turkey Tux). I’m going to live that head-to-toe sweats look this weekend.

  • Andrea

    As if you will have to convince Haley….

    • Harling Ross


  • Caro A


  • Kayla

    What size are you wearing in the amazon fashion sweats?

  • You killed it Harling!! Also, can we get that ManRepellar cap??????

  • Cat Mossing

    I am in love with the Donna Tartt Vibe look!!! Literally buying it right now…

  • Christine Russo

    The trick to a beret is actually putting it on your head 🙂 (no shade)

    • Harling Ross

      hahahah thanks for the tip

  • Rosemary

    Okay call me crazy, I know “Whoever said orange was the new pink was seriously disturbed,” but I have a strong premonition of it becoming the new Gen Z yellow

    • Harling Ross

      !! interesting !!

  • Bee

    I’m loving Look #5!

  • Yeeeesss all of these outfits are amaaazing, Harling!

  • Love this

  • Nancy

    I come here to read everything, but I stay for the Harling fashion posts, especially when she or Haley or the other MR girls are modeling. The models are nice, but I like the editors in the clothes better.

    • Harling Ross

      we have some content coming up you’re gonna loveeeeee !

  • Peyton Lee

    The last one is the best by far, Harling! You keep effortlessly pulling off that Saks Potts coat! Great article!

  • Lunasol Villanueva-Nagy

    Look 3 I really liked on you a lot although I loved all the looks.

  • Haw! Haw! I absolutely love it!

    I prefer to do my own fashion thing, but if I were inspired by any of the above then it would be:

    Look 2 for work: I’m a corporate person living in Germany, so the suit would be conservative enough for my field, but I’d change the colour to grey striped, navy, dark green, brown, or purple, ditch the white socks for bare skin or nude tights, and wear your shoes instead of hers!

    Look 1 for winter: But only the leopard statement coat, as I detest the “drab” look!

    The fashion me is probably Look 4! However, I don’t like sweaters or jumpers as I’m allergic to the material so, I’d find something else, but definitely keep the burnt orange, tweed trousers, orange purple/brown scarf, and black gloves combination!

  • liis

    eccentric octogenarian FTW

  • june2

    You look wonderful in every single one! It looks like you care about yourself, in all the right ways. Way better than no effort/too safe/or something overly outrageous

  • b.e.g.

    Harling, you are the cutest.

  • b.e.g.

    I do have some thoughts on the various street fashion looks …. I have been wearing some of these ecclectic looks forever, but why hasn’t anyone photographed me???

    Look #6, been there, done that. I am going to sell my furry sweater on ebay, probably get some good dough now that it’s been featured in MR!! Look #5 I do this still because I love hoodies, and they protect my hair from unexpected rain for one, and make my coats warmer for two, and so on. Look #4 – my favourite of your looks, one suggestion, tilt the beret a little and down forehead a little more – I always mix prints in the same colour hue, flowers, stripes, geometric shapes, whatever, I can make it work. Berets make any outfit look sophisticated. Look #3, not me, I am too short to layer that way. Look #2, looks great on you, but I was in my 20s in the 80s and just cannot bear the too wide shoulder look. Once was enough for me. Ugh! I cringe when I look at old photos. Look #1, love your take on it better. Animal prints rule! Shoes, bags, coats, sweaters, one piece. Love.

  • Kasey

    The suit is actually my fav look I’ve ever seen on you!

    • Harling Ross

      THANK YOU. maybe i’ll have to give it another chance

  • Erin Taylor

    I agree that street style does seem more attainable than looks right off the runway, but for me, the question isn’t so much of how to wear these looks, it’s “where?”. While these obviously aren’t dressy like couture, it seems a little extra to wear something like this everyday to class or to the mall. Maybe out to a cool lunch? Or, maybe my life is boring?

    • Rosemary

      I dress “extra” for class because it makes me more excited, motivated, and ready to face the day! But then again, I go to a school where people don’t really care about fashion in the sense that there are no real “trends” and the sorority-girl oversize Tshirt and athletic shorts/leggings default outfit isn’t so ubiquitous. People wear anything from PJs to heels, so while I do get some weird looks, I’m comfortable just wearing what makes me feel like me! My life is pretty boring in the sense that it’s mostly school-dominated haha, but we can always dress like it’s not 🙂

  • Tse Paco

    I love look 5!!


  • Modupe Oloruntoba

    The everything but the kitchen sink interpretation is so far away from what I usually like (with the exception of leathers, I would ban brown fabrics if I could), but I love love love Harling’s take on it!