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.
Jackets
Swap your cold-weather jackets for something light and versatile during the spring-summer transition.
Who What Wear
Striped Long Sleeve Shrunken Trucker Jacket
This neutral striped trucker is the perfect layer for wearing over all your weekend outfits.Available in sizes S to 4X.
Who What Wear
Leaf Print Long Sleeve Military Jacket
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.
Who What Wear
Long Sleeve Wrap Blazer
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.
Tops
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.
Who What Wear
Sleeveless Button-Back Tank Top
Style this tie top with anything from a midi skirt to trousers, depending on the day. Available in sizes XS to 4X.
Who What Wear
Striped 3/4 Sleeve Oversized Tunic
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.
Who What Wear
Short Sleeve Knit to Woven Corset Dress
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.
Who What Wear
Floral Print Long Sleeve Midi Shirt Dress
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.
Who What Wear
Striped Sleeveless Asymmetric Hem Shirt Dress
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.
Bottoms
Whether you're into pants, skirts, or both, the best transitional bottoms are the ones you can get tons of use out of.
Who What Wear
Wide Leg Tailored Crop Trouser
Style these with anything from a sweater on cold days to a T-shirt on warm weekends.Available in sizes 2 to 26.
Who What Wear
Striped Flowy Asymmetric Midi Skirt
I can imagine this print looking good with both summery sandals and pumps.Available in sizes 2 to 26.
Who What Wear
Wide Leg Tailored Crop Trouser
Sorry, but these pants are so good we had to include both colors.Available in sizes 2 to 26.
Who What Wear
Button Down Birdcage Skirt
Consider this a skirt substitute for your go-to jeans.Available in sizes 2 to 26.
Accessories
To me, a transitional accessory is anything that can balance an otherwise too-wintery or too-summery outfit. See what I mean below.
Who What Wear
Cube Crossbody Bag
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.
Who What Wear
Mae Patent Heeled Slide Sandals
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.
Who What Wear
Martha Crossbody Bag
Conversely, if you look feels too summery for this transitional weather, a darker crossbody bag can make it just right.
Who What Wear
Ruth Toe Ring Wood Heeled Pumps
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.
Since starting as an intern back in 2013, Nicole Akhtarzad Eshaghpour has held several roles here at Who What Wear, and she is currently Editor-at-Large. Upon joining, she was a senior about to graduate from business school at USC. Fast-forward to 2025, and she's moved to NYC from her hometown of Beverly Hills and spends her workdays a little differently from when she was just starting out. Currently, she focuses on a weekly mélange of shopping content and her Trust Me—Buy This newsletter. As far as her personal style goes, she's largely drawn to neutral, classic pieces but will always make an exception for something colorful or bejeweled as long as it's deemed worthy enough. After all, the only thing she loves more than a party is dressing up for one. On her downtime, she can usually be found at home eating something delicious and trying to force her husband to watch Summer House.
