7 Transitional Weather Essentials to Wear This Fall (and Spring)

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 AM, in front of my floor-length mirror, I loved (loved!) my outfits. By 3 PM, 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.

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

Alex Mill Nico Chunky Cardigan
Credit: Alex Mill
Cropped Cashmere Cocoon Cardigan
Jenni Kayne Cropped Cashmere Cocoon Cardigan
Credit: Jenni Kayne
Zanzibar V-Neck Cardigan
Loulou Studio Zanzibar V-Neck Cardigan
Credit: Nordstrom
Scarlet Cashmere Cardigan
Khaite Scarlet Cashmere Cardigan
Credit: Net-a-Porter
Striped Cardigan
JoosTricot Striped Cardigan
Credit: Revolve
Zoe Oversized V-Neck Cardigan
Leset Zoe Oversized V-Neck Cardigan
Credit: Olivela

“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

Chocolate Brushed Leather Loafers
Prada Chocolate Brushed Leather Loafers
Credit: Prada
Whitney Super Lug Loafer Flats
GH Bass Outdoor Whitney Super Lug Loafer Flats
Credit: Bloomingdale’s
Marcie Croc-Embossed Leather Loafers
Aquatalia Marcie Croc-Embossed Leather Loafers
Credit: Saks Fifth Avenue
Mikki Leather Short Boots
Schutz Mikki Leather Short Boots
Credit: Saks Fifth Avenue
Elise Slim Ankle Bootie
Loeffler Randall Elise Slim Ankle Bootie
Credit: Loeffler Randall
The Mid Heel Suede Ankle Boots
TOTÊME The Mid Heel Suede Ankle Boots
Credit: Net-a-Porter

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

The Agnelli Sock
Comme Si The Agnelli Sock
Credit: Comme Si
Cotton Socks
Celine Cotton Socks
Credit: Celine
Ritz Socks
Frame Ritz Socks
Credit: Frame
Set of Two Intarsia Stretch Socks
SOCKSSS Set of Two Intarsia Stretch Socks
Credit: Net-a-Porter
Missoni Women's Short Socks, 001 Black/White, One Size
Missoni Missoni Women’s Short Socks, 001 Black/White, One Size
Credit: Amazon
Everyday Crew Sock
SKIMS Everyday Crew Sock
Credit: SKIMS

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

Khaltoum Matte Black Sunglasses
Nessy Khem Khaltoum Matte Black Sunglasses
Credit: Nessy Khem
Dixie Sunglasses
Vehla Eyewear Dixie Sunglasses
Credit: Vehla Eyewear
Valentina Sunglasses
DMY BY DMY Valentina Sunglasses
Credit: Anthropologie
Women's Square Sunglasses - 150th Anniversary Exclusive
Gucci Women’s Square Sunglasses – 150th Anniversary Exclusive
Credit: Bloomingdale’s
Zawe Cat-Eye Sunglasses
Kimeze Zawe Cat-Eye Sunglasses
Credit: Net-a-Porter
Debbie D-frame Sunglasses
Linda Farrow Debbie D-frame Sunglasses
Credit: MatchesFashion

“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

Loa Dress
Ba&sh Loa Dress
Credit: Ba&sh
Wells Dress
Staud Wells Dress
Credit: Staud
Contrast-Tipped Midi Dress
Self-Portrait Contrast-Tipped Midi Dress
Credit: Net-a-Porter
Irene Dress (Extended Sizes)
Rixo Irene Dress (Extended Sizes)
Credit: Rixo
Asymmetric-Hem T-Shirt Dress
Balenciaga Asymmetric-Hem T-Shirt Dress
Credit: MatchesFashion
Fitted-Waistline Midi Dress
Marni Fitted-Waistline Midi Dress
Credit: Farfetch

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

High Sport Kick Pant
High Sport High Sport Kick Pant
Credit: Moda Operandi
Camille Check Flared - Leg Pants
Tibi Camille Check Flared-Leg Pants
Credit: Bergdorf Goodman
Zoe Knitted Wide-Leg Pants
LESET Zoe Knitted Wide-Leg Pants
Credit: Net-a-Porter
Stretch Jersey Knit Straight Pant
Eileen Fisher Stretch Jersey Knit Straight Pant
Credit: Eileen Fisher
Plus-Size Double Knit Wide-Leg Pant
Lafayette 148 New York Plus-Size Double Knit Wide-Leg Pant
Credit: Lafayette 148
Jet Twist Pants
JoosTricot Jet Twist Pants
Credit: JoosTricot

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

Cropped Trench Jacket
Thakoon Cropped Trench Jacket
Credit: Thakoon
Cotton Cargo Jacket
Toteme Cotton Cargo Jacket
Credit: MyTheresa
Shell-Trimmed Twill Jacket
SACAI Shell-Trimmed Twill Jacket
Credit: Net-a-Porter
Marine Jacket
Nili Lotan Marine Jacket
Credit: Nili Lotan
Classic Utility Jacket
Universal Standard Classic Utility Jacket
Credit: Universal Standard
Suede jacket
Loewe Suede jacket
Credit: Loewe

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.


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