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 bagVintage 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. 

Harling Ross

Harling is a writer and was most recently the Brand Director at Man Repeller.

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