How To Wear Fall’s Most Impossible-To-Style Fashion Trends

When you work with garments day in and day out, they begin to blur together — another white tee, another pair of jeans, another stiletto kitten heel. So when something shocking comes along, fashion editors are eager for the challenge. Our brains start whirring like the outfit tracker in Clueless, swapping out handbags and shoes and jeans and skirts in search of the perfect combination.

At fashion week, the runways churned out decidedly dramatic looks, making tricky-to-style trends — thankfully — abundant this season, from denim accessories and extra-large statement belts to the ever-intimidating monochromatic red ensemble.

Out-of-the-norm styles are also trickling upward from the streets and social media. The humble soccer jersey, for example, has been styled eclectically by influencers and celebs alike (see: Kim Kardashian, Bella Hadid, and Julia Fox).

As is tradition, I rounded up my co-workers and challenged them to style the hardest-to-wear trends on the market — and naturally, they did it with ease. Keep reading to see Bustle’s most stylish editors do what they do best: make these tricky looks seem oh-so-chic.

Soccer Jerseys

“I’m not the sportiest of girlies, so trying to incorporate a soccer jersey from a team I know nothing about seemed a little intimidating. The best approach I found was to fully lean into the sporty vibe. I paired it with my baggiest — and softest — jeans and mirrored shield sunglasses. Instead of a traditional leather purse, I decided to go with a silver metal pouch bag to give the outfit a bit of an edge. I’m sorry to all the Arsenal fans who stopped me to chat — I just really love the colors!” — Stephanie Sanchez, Senior Fashion & Accessories Editor

Denim Accessories

“I built this look around Diesel’s buzzy 1-DR bag in embellished denim. In line with the bag’s blingy details, I opted for a pair of foiled silver jeans and an early-aughts-inspired denim patchwork belt. To balance the flashier pieces, I chose grounding basics — a white tank top, boxy black blazer, and black cowboy boots. I found that the denim accessories were neutral enough to match a lot of pieces, while simultaneously adding an updated flair. For a final touch, I topped the ensemble with a pair of futuristic reflective shades.” — Copelyn Bengel, Accessories Editor

Maxi Skirts

“Maxi skirts can be difficult to style due to their overwhelming, sometimes frumpy shape. But through much research and development (read: wearing a lot of maxi skirts), I think I’ve nailed it. Though I usually reach for denim maxis, this time I went for a fabric I’d never tried before: satin.

The column silhouette felt very ‘my husband died under mysterious circumstances and I’m set to inherit his fortune,’ so I leaned into that aesthetic. A vintage blazer-style top from the ’80s and my poshest loafers only added to the stealth wealth feel. Naturally, pearls were my gemstone of choice, and I polished off the look with a classic red lip.” — Kelsey Stiegman, Senior Fashion Editor

Head-To-Toe Red

“I love wearing red, and my bin of Nars lipstick is proof — so when I was tasked with the challenge of wearing the color from head to toe, I knew it was a test I would enjoy. Though monochrome can feel daunting — particularly in this shocking shade — playing with texture and accessories is the way to have fun with it. The tonality of different fabrics adds a bit of dimension to the outfit. I went for a mod-shaped mini dress, styling it with red tights and patent ballet flats.” — Eunice Bruno, Associate Fashion Editor

Statement Belts

“I’m a big lover of nostalgic fashion throwbacks. It’s thrilling to see trends — like one of my past favorites, wide belts — reemerge from the ’90s or early 2000s. Even more thrilling is giving them a modern spin. I love remaining true to my past self while also making yesterday’s wardrobe staples work for today.

The black leather and sleek silver hardware on this chic Michael Kors belt makes the early millennium a distant memory. I wore it over the Wolford Fatal Cut-Out dress, which you can style multiple ways. (I chose ruched and short.) And although I’ll love those Y2K oversize bags, I chose to minimize the baggage and go with the most perfect, compact Brandon Blackwood piece.” — Jennifer Yee, Fashion Market Director

Photographs by Xin Xin

Makeup and Hair: Ashley Webb

Photo Director: Alex Pollack

Editor in Chief: Charlotte Owen

SVP Fashion: Tiffany Reid

SVP Creative: Karen Hibbert