How to Dress for Transitional Weather Without Going Crazy

If you find transitional dressing to be annoying, confusing, a waste of money, or all of the above, this roundup is for you. After all, I get it. You're all like: Is it hot? Is it cold? What do I wear when it's multiple temperatures in one day? Am I wasting money on these in-between clothes?

Not to worry, though, because I'm here to make all those questions go away. Not only am I telling you what you can wear for in-between weather, but I've chosen pieces that can work across multiple seasons so that even if they weren't all under $50—which they are—you'd be getting your money's worth.

Shop the very best transitional pieces from our very own Who What Wear collection broken down by category below.


Swap your cold-weather jackets for something light and versatile during the spring-summer transition. 

This neutral striped trucker is the perfect layer for wearing over all your weekend outfits.

Available in sizes S to 4X.

If you're looking for an of-the-moment outerwear choice that still feels right for the season, opt for an ultra-cool camo-inspired jacket.

Available in sizes S to 4X.

Fluctuating temps make dressing for work especially hard, so something like this light wrap blazer is perfect for keeping you concealed under the frigid AC vents, but not weigh you down too much on warm days.

Available in sizes S to 4X.


If you're investing in new tops during transitional seasons, they should always work for the climate ahead as much as the one you're currently in.

Style this tie top with anything from a midi skirt to trousers, depending on the day. 

Available in sizes XS to 4X.

A button-down tunic is the everyday blouse your spring and summer work wardrobe needs.

Available in sizes XS to XXL.


What makes the perfect transitional dress? Anything from neutral tones that work across multiple seasons to layerability to both.

Starting off with my personal favorite, as you can see this deceptive dress appears to be a skirt and a top, but it requires no effort to put together. Just add shoes.

Available in sizes XS to 4X.

Shirtdresses are so good for transitional dressing that we couldn't just choose one. Starting off with this striped number, it's perfect for layering under sweaters and jackets or wearing on its own.

Available in sizes XS to 4X.

Back to my favorite camo-inspired print, this dress is not just pleasing to the eye, but it's also neutral enough for wearing in both cold and warm months.

Available in sizes XS to 4X.


Whether you're into pants, skirts, or both, the best transitional bottoms are the ones you can get tons of use out of.

Style these with anything from a sweater on cold days to a T-shirt on warm weekends.

Available in sizes 2 to 26.

I can imagine this print looking good with both summery sandals and pumps.

Available in sizes 2 to 26.

Sorry, but these pants are so good we had to include both colors.

Available in sizes 2 to 26.

Consider this a skirt substitute for your go-to jeans.

Available in sizes 2 to 26.


To me, a transitional accessory is anything that can balance an otherwise too-wintery or too-summery outfit. See what I mean below.

If black is your go-to clothing color year-round, add a light bag like this to your look to make it feel more of-the-moment seasonally.

Swap your cold-weather shoes for sandals and your daily jean and T-shirt look will be ready to go for spring.

Available in sizes 6 to 11.

Conversely, if you look feels too summery for this transitional weather, a darker crossbody bag can make it just right.

Sandal weather means we're wearing these the first chance we get. Plus, the wooden heel makes them feel so versatile in both red and black. 

Available in sizes 6 to 11.

Want more affordable finds? Shop our full Who What Wear collection here