All seven days of New York Fashion Week, I came head-to-head with the same minor wardrobe emergency and lost every time. At 7 A.M., in front of my floor-length mirror, I loved (loved!) my outfits. By 3 P.M., those same outfits were either too hot, too cold, or too unsuited to the elements. Cue the endless fidgeting and finessing trips home to change, instead of focusing on the real point of fashion week—the runways.
This is one manifestation of the biannual dilemma brought on by tricky transitional weather. No matter how many times you check the Weather App or repack your bag, fluctuating temperatures and unpredictable forecasts can challenge even the most experienced dressers between March and April, August and September. “It’s almost like you forgot how to dress when the weather changes,” agrees Natalie Joos, founder of JoosTricot. “After a hot summer I always have difficulties figuring out how to layer.”
But, Joos continues, tackling transitional weather outfits is like riding a bike—it takes practice and a dose of patience. With the right mindset, it’s even a moment to get creative with pops of color and layering combinations, LeSet founder Lili Chemla adds. “For me that means sweaters over shoulders, ankle socks with shoes, and my current obsession is a long sleeve tee under a slip dress—embracing a ’90’s moment,” she says.
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As for what to actually buy in these moments? “Winter-to-spring transitional pieces are certainly the most difficult pieces to spot and style,” says The Nines in-house stylist Lisa Sanchez, “but the search for other seasonal transitional pieces can be easier than you think.” Ahead, find seven expert-recommended essentials to get started.
The Forever Cardigan
“Focusing on staples that lend themselves to endless styling is essential for these moments in between seasons, and a classic cardigan can really do it all,” designer Jenni Kayne tells us. The limit on ways to tie, drape, or button a cardigan over anything almost doesn’t exist. Exhibit A: Bella Hadid’s one-arm-in, one-arm-out sweater styling.
There are also more conventional cardigan styling routes, all primed for days when the temperature swings from chilly to sizzling: draped over both shoulders, tied around the waist, or buttoned up all the way. Get layering with one of the standout cardigan options recommended by our experts above, from boxy and cropped to slouchy and oversized, or check out the complete edit of BAZAAR editors’ absolute favorite knits.
The In-Between Shoe
Between designers, editors, and stylists, two shoe styles rose above the rest as the best to wear before it’s actually fall (and also after). First, walkable loafers to add a prep-lite touch to casual outfits. Second, ankle boots to give day and night looks some lift without the heft—and heat—of a true winter boot. Just make sure to keep the shades neutral: Sanchez says they’re the easiest tones to coordinate with late summer and fall palettes, making early-morning accessorizing a breeze.
The Layering Socks
Presenting the perfect complement to those summer-to-fall shoes above and the accessory all of New York Fashion Week street style had in common this season. Chemla rotates Comme Si ankle socks through a few transitional outfits where hers are a must: with a loafer and mini-dress; with slides, cropped pants, and an oversized button-down; or with a knit sweater and tank.
The All-Year-Round Shades
“Sunglasses are usually thought of as a summer moment,” says BAZAAR contributing fashion editor Kerry Pieri, “but I love how the right ones paired with a turtleneck sweater and jeans look so cool.” She designed a capsule with Nessy Khem that combines matte frames and tinted lenses for a sharp summer-to-fall look (literally). If you’re playing it classic, go for a slight cat-eye or square shape in neutral matte or tortoiseshell for the most mileage. Whichever pair you slide on, “Add a gold chain necklace to get all the Old Celine ad vibes,” Pieri suggests.
The Multi-Season Midi Dress
Here’s a one-and-done essential you can wear year-round, tricky in-between days included. Sleeveless or short-sleeve dresses in breathable poplins can be layered with a tissue T-shirt when it’s cold; until autumn officially kicks in, more modest cuts are ready as they are. Sanchez recommends polka-dot or floral dresses for a pop of something extra.
The stylist adds that Jennifer Lopez’s rotation of end-of-summer dresses is a lesson in transitional weather styling if you’re in need of inspiration. The same piece that’s 80-degree perfection with nothing but a platform sandal remains relevant with an oversized blazer or sweater on cooler days.
The Knit Pant
Knit bottoms are the breathable, versatile alternative to jeans or khaki pants, whether you double up on soft textures with that cozy new cardigan or try some off-duty model juxtaposition in an oversized button-down. Joos often styles her pairs with a long-sleeve crop top for transitional weather: Together, they’re “still breezy and light but covered enough for a chilly night.”
The Lightweight Jacket
Bloomingdale’s ready-to-wear fashion director Arielle Siboni predicts all things utility—Cargo pants! Bomber jackets! More cargo pants!—will continue dominating fashion throughout the fall and into next spring. Lightweight utility jackets from Nili Lotan to Sacai address the infatuation; they’re also an ideal in-between layer for days that start and end chilly, but hardly require a puffer coat. If other items in utility’s aesthetic family fall back out of fashion, these jackets’ classic lines and comfort-first designs are impervious to trends—meaning they’ll be your final transitional weather layer from now until forever.
Halie LeSavage is a New York City-based writer and editor for Bazaar.com, where she covers all things e-commerce and shopping. Her work has previously appeared in Glamour and Morning Brew.
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