13 transitional weather pieces I wear every single year

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Lauren Caruso is an In The Know shopping contributor. Follow her on Instagram and Twitter for more.

There’s something formulaic about getting dressed when you’re in the thick of a particular season — and that’s been especially true since the beginning of the pandemic. In summer, it’s usually some combination of shorts and a basic tee, while winter calls for layering of the same few pairs of sweatpants, a sleeping bag-puffer coat and the warmest boots you own. It’s the in-between seasons — those few weeks of transitional weather when it’s not quite freezing anymore, but you still have to resist the urge to jump the gun and bare your arms or legs lest you, well, freeze — that can make dressing difficult.

Those few days (as fleeting as they are in New York City) are my absolute favorite. There’s usually a collective sigh that we (probably) won’t have to deal with a record-breaking snowstorm for another six months — and everyone’s just generally more excited to get outside, even if just for a few socially-distanced minutes. Still, getting dressed for the first few weeks of spring can be tough, but I’ve noticed that I rely on the same few mainstays to get me through the thick of it.

First, proper footwear is essential: I may rearrange my closet so my slides and mules are at the ready. I usually find myself reaching for something more practical, like a lug-sole sneaker. Same goes for the rest of my outfit: While I’d love to parade around in ribbed tank tops all day, it’s still important to layer — even if those layers are less insulating. 

Check out the 13 transitional weather staples I wear every single year below — plus the best ones to shop right now. 

Crew-neck sweatshirt

There’s no single item in my wardrobe that I’ve gotten more use of out in the last year than my Champion crew-neck sweatshirt — and I’ve had the same one for at least a decade. I wear mine with wide-leg pants or jeans for a quick coffee run, or with shorts if I’m actually venturing outside for a socially-distanced outing with friends.

Shop: Champion Reverse Weave Classic Crew Neck Sweatshirt, $54

Credit: Urban Outfitters

Trench coat

I don’t need to convince anyone that a trench coat is a springtime staple. This asymmetrical two-toned style from The Frankie Shop is a fun take on the classic silhouette. 

Shop: Two-Tone Asymmetrical Trench, $295

Credit: The Frankie Shop

Comfortable joggers

Is there any single item that’s worked more overtime than a simple pair of joggers? This style from Aritzia fits snug enough to still make me look presentable. I’ll pair them with a white tank and single-strap slides — once the weather complies.

Shop: Tna Cozy Fleece Boyfriend Basic Sweatpant, $70

Credit: Aritzia

Lug-sole shoes

If you live in New York, you know there’s a span of two months — usually right around the official start of spring — where the weather forecast includes both 68-and-sunny and a blizzard warning, all within one week. After said snow storm, a pair of lug-sole oxfords like these from Ganni seem all the more seasonally appropriate.

Shop: Ganni Chunky Sole Oxford Shoes, $356

Credit: Farfetch

Cropped sweater

A throw-and-go sweater is great for any season, but particularly useful for early spring days when a tee or a tank isn’t enough coverage. This cropped style from Source Unknown looks just as great with joggers or leggings now as it will with a mini skirt later.

Shop: Source Unknown Plunge-Neck Cropped Knit, $52

Credit: Source Unknown


I’ve been wearing these versatile oversized shirts as a more casual jacket substitute for years, but only recently discovered they have their own name: shackets.

Shop: Zara Faux Suede Overshirt, $49.90

Credit: Zara

Knee-high boots

A good pair of knee-high boots is a transition weather staple. Not only do they feel like a makeshift pant when paired with midi skirts, but they look just as great with jeans and a tank when it’s finally warm enough for them.

Shop: Miista Inga Grigio Nappa Leather Boots, $645

Credit: Miista

Springy mules

Sure, these err on the warmer side of transition months. But there’s something about the first crisp spring morning where baring your legs (or, in this case, your toes) feels like freedom.

Shop: Simon Miller Bil Thong Sandal, $390

Credit: Simon Miller

Slip dress

A ‘90s-inspired slip dress is perfect for any season, but that’s especially true for spring and fall days. While it’s still freezing out, I pair mine with a turtleneck and a long-line jacket for a look that’s put together, then I ditch the layers and sub in a cropped cardigan when it’s warm enough to bare (some) skin.

Shop: Silk Laundry ’90s Silk Slip Dress, $295

Credit: Silk Laundry

Wide-leg pants

These wide-leg pants are made from a seersucker material, giving them the illusion of presentability. (The good news is that they still feel like sweatpants.)

Shop: Oak + Fort Elastic Waist Pants, $68

Credit: Oak + Fort

Leather jacket

A classic leather biker jacket is great for any season, but especially for when it’s warm enough to leave the puffer at home but there’s still a chill in the air.

Shop: Mango Zipped Biker Jacket, $79.99

Credit: Mango

Straight-leg jeans

There’s something timeless about a pair of non-stretch, straight-leg denim. This season, should I decide to put on jeans, this pair from Citizens of Humanity will be my go-to pair for the fourth year in a row.

Shop: Citizens Of Humanity Straight Fit Jeans, $218

Credit: Citizens of Humanity

Single-button blazer

During transition-weather months, a good blazer also doubles as a jacket. I like to wear mine with a hoodie underneath until it’s warm enough to just layer it atop a ribbed white tank.

Shop: Toteme Wool-Blend Blazer, $700

Credit: Net-a-Porter

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