Why Fall Is The Best Fashion Season

A new season always comes with excitement — some more so than others. Ahead of spring, it’s the promise of thawing snow, longer days, and shorter hemlines, while winter comes with holiday festivities to look forward to, from Christmas to Valentine’s Day. Summer is, well, summer. But no amount of cashmere sweaters or pumpkin spice lattes can save fall from having the worst reputation of all, as we segue from carefree summer sunshine into dropping temperatures and 4 p.m. sunsets. For many, the season evokes a sense of impending doom that ignores a real opportunity hiding in the turning (and yes, falling) of the leaves: dressing up.

Even though I grew up in the Caribbean, I was always aware of fall’s style potential. I’ve been a fashion fan since I could form a thought, and it seemed unfair that other people could celebrate the changing of the seasons with a new jacket or sheer tights when I was only allowed the occasional hoodie or ankle boot. During college, I started to realize that fall fashion wasn’t just about seasonality, but rather a mindset: Why should my outfit be limited to two-piece sets or a maxi dress just because it’s 85 degrees? So I ditched the tank tops and breezy dresses for leather jackets and long-sleeve shirts, and adapted my approach to fashion to embrace layering. Leandra Medine’s Man Repeller, which featured a column called “Lessons In Layering,” was my go-to guide, teaching me to layer tank tops with various lengths to form a mini dress, or wear a pencil mini skirt over a cotton dress. 

Later, when I finally moved to New York, I discovered I was right all along. Even with a closet of mostly black clothes, my styling opportunities multiplied, thanks to the cooler temperatures: A ribbed knit halter bodysuit suddenly became just another layer to keep piling onto, knee-high socks entered my fashion vernacular, and I could finally wear my beloved leather jackets in their appropriate environment. 

Year after year, when people around me start cursing the change of seasons, I can only think, “You have it so good and don’t even know it.”

The season’s sartorial capabilities are best on display during the fall fashion weeks; a mix-up of incongruous outfits featuring pieces that would otherwise never be paired together, but that actually act as a flex of styling muscles. Miu Miu’s fall 2022 collection, for example, showed polo shirts fit for Blair Waldorf’s PE class with knee-high socks and ballet flats; Bottega Veneta included tank dresses with thigh-high slits and a ruffled hem, paired with knee-high boots; and Marc Jacobs featured larger-than-life oversized pink denim over a slinky silver bralette, paired with opera gloves. The possibilities are just endless. 

Because fall is the only season without climatological challenges (unless hurricane season gets in your way) — summer comes with intolerable heat, winter only brings darkness and dirty snow — it’s also truly a special time to not only layer up, but play with fashion. Want to add a leather mini skirt over that white shirt dress so there's a bit peeking out from the skirt’s hemline? Go for it. Feel like wearing head-to-toe leather to catch a matinee of Don’t Worry Darling? ‘Tis the season. Longing for a slip dress-and-boots moment? Be my guest. 

One thing about fall styling is that it also allows us to ditch who we are for who we want to be — fashion-wise, that is. When we are spoiled with good weather, there are fewer factors to inhibit our desire to fully express ourselves through fashion, giving us the chance to try different facets of our personalities or even dress in a new one. Without this yearly exercise — one that forces people to be honest with their personal style via transitional dressing — we’d be stuck falling into winter without any dress-up fun. In turn, when style personalities come out to play, streets, bars, cafés, offices, and trains become an everyday moodboard of fashion inspiration. 

This year’s lineup of fall trends is especially exciting, leaving behind the ultra-slinky, somewhat gimmicky Y2K-revival styles of the past two years for multifaceted choices that highlight the best of personal style: metallic hues and materials, menswear-inspired tailoring that somehow feels fresh, head-to-toe biker chic leather, Barbiecore pink, skirt suits, ‘80s shoulder pads, Gossip Girl-ready preppy fashion, and opulent outerwear that’s meant to do more than just warm you up. 

So, will you come out to play?