5 Transitional Pieces I'm Taking Into Fall — And How To Wear Them

Fall has entered the chat... and so has the looming feeling that I need a brand new wardrobe to accompany the change in weather. However, this upcoming season, in an effort to save my wallet, the planet, and the dormant clothes that I don’t wear enough, I have decided to extend a VIP invitation to a few select, transitional staples from my summer closet to join me in welcoming fall. If executed effectively, this capsule closet could be utilized year-round — but for now, let’s focus on how to take it through the months ahead.

As evidenced by the renaissance of street style that’s come with the return of in-person fashion weeks, there are a select group of current trends that lend themselves to a change in seasons. Vests, button-downs, lug sole boots, Bermuda shorts, and slip dresses are all pieces that I’ve seen styled just as effortlessly for cold weather as I’ve seen for sweaty days. Relying on a healthy mix of trendy pieces and closet classics will not only limit my time in fitting room lines this fall but will also re-introduce me to the forgotten relics of summer that I didn’t wear quite as many times as I swore that I would. So, if like me, you aim to be trend-facing but want your closet to transcend the seasons, then this is the shopping list for you.

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Vests

Vests are what I call a “nine-life trend,” appearing in multiple forms this summer and fall — most notably in the form of sweater vests, Y2K suiting, and quilted iterations. For warm weather, the vest-as-shirt trick has been adopted by A-listers like Kendall Jenner and Bella Hadid. While this may last through September, come true fall, these same vests can be paired over your go-to button-down or turtleneck with trousers, jeans, or a midi skirt for a sophisticated fall fit.

Button-Downs

I myself have recently inherited a white button-down, and it has sparked a new appreciation in me for the timeless piece. I have worn it all summer long as a cover-up, denim-shorts accomplice, and Zoom-call sidekick — the possibilities for a lightweight button-down are truly endless. Transitioning to fall, I plan to update the look by styling the crisp classic over slip dresses and turtlenecks; and under sweater vests, blazers, denim jackets, you name it.

Lug Sole Boots

Functionality may just be the most important quality to look for in a capsule wardrobe piece, and knee-high lug sole boots are synonymous with function — and fashion. One of my favorite unexpected ways to see these stompers in the summer is with a babydoll dress — and the fall outfit possibilities jar hasn’t even been opened. Pair the boots with vintage denim, leather trousers, and slip dresses, or tuck them into your suit pants. If I wasn’t already sold on the chunky, functional sole, I’m convinced that this shoe is going to be one of fall’s (and winter’s) trendiest boots.

Bermuda Shorts

Stay with me on this one, Bermuda shorts may seem like a forgotten early aughts flashback that you haven’t reconciled with your gaucho phase, but for fall, they’re here in a clean, tailored way. Whether it be a perfect hem or a well-placed pleat, these knee-grazing bottoms are your pseudo trouser for summer to fall. My personal styling preferences include a breezy button-down or classic T-shirt for the higher temperatures into a smart blazer or chunky knit for the chiller months.

Slip Dresses

While slips may initially read summer or spring, I firmly believe they will have a stronghold over my fall wardrobe as a layering staple. In a more classic play, wear your slip dress with a playful summer bag and sandals during warm-weather months. When the chill creeps in, I plan to style my silk number under my favorite blazer or cozy sweater or over a simple T-shirt or bodysuit. This is me signing an official petition to keep luxe loungewear chic and relevant.