Monday, April 6

10 Transitional Outfit Ideas for Those Chilly and Illusive 50 Degree Days


  • It’s that time of the year when it’s 50 degrees outside, and getting dressed is a feat.
  • Cozy sweaters, fun patterned pants, and unique jackets are to the rescue.

There is this particularly challenging time of the year that always comes around and has me wondering: how do I dress today? That’s right, it’s 50 degrees out. When the seasons change, I’m stoked for the leaves turning various shades of orange and red and pumpkin lattes hitting my favorite cafe, but sometimes it takes a minute for my brain to get into cool-weather dressing. I’m thrown off my game and suddenly I’m having amnesia from the year before. 

Getting into the mindset of 50-degree weather dressing can be a challenge on its own, but actually putting together an appropriate outfit is an entirely different beast.

“I think that people sometimes have a hard time with 50-degree dressing because they don’t think they can make sweaters and coats look cute,” said stylist Zoe Gofman. “I also think that thicker materials tend to make people feel frumpy.”

Luckily, Gofman says a simple fix for this fear is to add “the right style tools and right garments”. She recommends getting creative with oversized jackets, fun boots, and, of course, making tights your best friend this season. “They are cozy and chic, and they go with everything.”

If you’re unsure how to take these ideas and translate them to a full ensemble, don’t sweat it. We’ve rounded up 10 outfit ideas using Gofman’s tips and tricks for how to dress for 50-degree weather days. From mini skirts paired with tights, cool leather jackets with baggy denim, and chunky knit sweaters, there’s fashion editor-approved looks for everyone during this confusing season.

Unexpected Athleisure

Passerby seen in Paris in September 2025.

Claudio Lavenia/Getty Images


In a sea of denim and sweaters, opt for a more unique ‘fit that works for this weather by styling a tracksuit to the nines. Make it a fashion statement by pairing it with chic boots or a pair of kitten heels and your favorite bag.

Dreamy Denim

Passerby seen in London in September 2025.

Hanna Lassen/Getty Images


Sometimes, a jacket can be the main focal point of a great outfit. A long denim jacket will surely keep you warm, and you might not even have to think about the top underneath. Show off even more personality by going with a patterned style.

Transitional Style

Passerby seen in Paris in October 2025.

Edward Berthelot/Getty Images


It may be reaching cooler temps outside, but that doesn’t mean you have to cover your legs. However, tights aren’t a bad idea. Pair with a mini skirt or shorts, then throw on a chic suede jacket for an easy yet trendy fall look.

Sharp (& Sensible) Accessories

Passerby seen in Paris in September 2025.

Claudio Lavenia/Getty Images


Accessories can make or break a solid outfit. Adding a cute silk scarf to your outfit not only adds a little extra warmth but also a little extra oomph to the ensemble.

Mix and Match

Passerby seen in Milan in October 2025.

Valentina Frugiuele/Getty Images


A longer skirt or dress from the warmer months can get a new life with a simple sweater. Throw on a trendy rugby polo sweater, or a cardigan or q-zip over your favorite midi or maxi frock to make the piece cold-weather-ready.

Classic Denim

Passerby seen in New York City in September 2025.

Edward Berthelot/Getty Images


When in doubt, jeans are always there for the transitional time of year. Whether you’re a fan of baggy, barrel, or are all-in on the skinny jean resurgence, paired with a simple top and light jacket, jeans remain a staple in the closet for a reason.

Tactical Layers

Passerby seen in Paris in October 2025.

Edward Berthelot/Getty Images


This time of year, the weather app can’t be trusted. Tie a sweater over your shoulders to earn extra trend points, and also be ready for a sudden overcast or wind tunnel.

Center Piece Coat

Passerby seen in New York City in February 2025.

Daniel Zuchnik/Getty Images


When it starts to get colder out, one can dread the thought of adding a coat to any look. Tackle that fear by adding a fun jacket to your wardrobe. Whether it’s a unique pattern or a cool texture, looking forward to wearing this frock (and styling outfits around it) can make a big difference.

Cozy Vibes

Passerby seen in Paris in October 2025.

Edward Berthelot/Getty Images


Not ready to commit to a coat yet, but trying not to freeze? Enter: chunky turtleneck. You can add it to virtually any bottoms in your closet, or throw it over a dress and have a cozy outfit ready to go.

Pants with Pizzazz

Passerby seen in New York City in September 2025.

Edward Berthelot/Getty Images


Though it may be time to put your summer sundresses away for the year, fun patterns can be part of the wardrobe year-round. Try a unique pair of pants with a jacket or sweater to take the style into the new season.



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