Fashion·9 min read

What To Wear When the Weather Is Yo-Yoing

transitional-outfit-ideas
Design: theSkimm | Photos: Madewell, Quince, Tuckernuck
September 11, 2026

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On days when it’s crisp in the morning but warms up by midday, what do you wear? We’re glad you asked. We’ve found lightweight sweaters, breathable pants, and stylish jackets. Repeat after us: light layers.

For more affordable, stylish outfit ideas, click here.

windbreaker

Madewell

Funnel-Neck Windbreaker Jacket

A funnel-neck windbreaker for brisk days…

When you definitely don’t need a parka but it’s a little chilly, reach for this windbreaker. The funnel-neck style is trendy and will actually keep you warm. Plus, the brown plaid print screams fall. 

trench

Tuckernuck

Khaki Drew Short Trench Coat

The perfect short trench coat…

A trench coat is a transitional weather staple, but we really appreciate the versatility of a short trench. This one looks great paired with jeans and a tee, provides enough warmth for a light layer, and is just the right amount of boxy. 

cardigan

Quince

Mongolian Cashmere Cardigan Sweater

A cashmere cardigan you’ll wear year-round…

Quince’s signature cashmere cardigan is lightweight, breathable, and relatively affordable. It’s made of 100% Mongolian cashmere that’s pill-resistant and is perfect for when you get cold at the office. 

rollneck

J.Crew

2025 Rollneck™ sweater

The J.Crew Rollneck™ Sweater…

This throwback sweater that J.Crew brought back last year has been taking the fashion world by storm. One editor owns a striped version and can confirm it’s made of cozy, thick cotton and is just the right amount of slouchy. 

leather-bomber

Abercrombie & Fitch

Funnel Neck Vegan Leather Bomber Jacket

Another funnel-neck jacket to add to your collection…

This one is made of soft vegan leather that looks like the real deal and reminds us of vintage aviator jackets. Wear it zipped up to block out the wind or unzipped over a tank

denim-shirt

Gap

Denim Big Shirt

A denim shirt that’ll always be in style…

Gap always does denim right, and this shirt is no exception. It’s oversized enough to look like you borrowed it from your partner, and it’s a layering piece you can easily throw on during a confusing weather day. We’re obsessed with the version that has the tiny bear on the pocket. 

chore-pants

Imogene + Willie

Ventura Chore Pant

A pair of chore pants that are more breathable than jeans…

For the in-between season, go with a pair of pants that’s more lightweight than jeans, like these cotton chore pants. They still have a substantial canvas feel to them and a relaxed yet polished fit. Plus, this shade of green is irresistible. 

cotton-sweater

Old Navy

Seaside Cotton Shaker Oversized Tunic Sweater

A crewneck sweater for all seasons…

A cotton sweater is your best friend when the weather can’t make up its mind. It won’t feel as heavy as one made with wool, and it’s softer and less scratchy. Layer a tee underneath so you can take it off if you get hot. 

denim-jacket

Reformation

Alex Cinched Denim Jacket

A denim jacket with a cinched waist…

If a regular denim jacket just won’t do it for you, may we introduce you to the showstopper you need? It has a chic cinched waist, a classic collar, and comes in a rich brown or just-right winter white (fall brides, grab this). 

set

No Boundaries

Ribbed Ballet Top and Flare Pants Set

An activewear set for errands days…

Whether you’re browsing the drugstore or standing in line at the post office, you’ll feel like an off-duty ballerina in this set. It comes with a cozy wrap top and matching flared pants that aren’t too tight. The ribbed fabric is stretchy and breathable. 

puma

Puma

Speedcat Cow Ballet Sneakers

A moo-re fun version of our favorite ballet flat sneakers…

We love how comfy this sneaker and ballet flat combo is, just like our trusty Speedcat sneakers. This cow-printed version is unique and will turn a basic outfit into a statement. If you often get hot feet, you don’t have to wear them with socks. 

baagy-jeans

Gap

Mid Rise UltraSoft Baggy Jeans

A super soft pair of mid-rise jeans…

These Gap jeans are so soft that you’ll feel like you’re wearing sweatpants. They’re made of non-stretch denim that still moves with you and isn’t restricting. The slouchy leg pairs well with sneakers or heels. 

cardigan-jacket

Anthropologie

Maeve Cotton Cardigan Jacket

A cardigan jacket we didn’t know we needed…

We’ve never seen a jacket quite like this one — it combines two of the best light layers: a cardigan and a barn jacket. Both striped colorways are trendy and cute, and the denim collar really pulls it together. 

aritzia

Aritzia

InterLock Cotton Steps Longsleeve

A classic long-sleeve tee…

We implore you to make sure you have a nice long-sleeve tee at your disposal. It’s perfect for in-between fall days, is made of breathable cotton, and looks good with any bottom. This one also comes in versions that look layered. 

joggers

FP Movement

All Star Solid Joggers

A pair of joggers that Goldilocks would approve of…

These are not too hot, not too cold, just right. They feel like your favorite sweatshirt and aren’t fleece-lined, so you won’t overheat if it warms up later. We love that they’re not paper thin like leggings, so you can count on them to see you through the day. The bright blue is calling our name. 

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