4 Chic Looks That Serve as the Ultimate Transitional-Weather Outfit Inspiration

We’re about to enter that tricky point in the year when it’s not extremely frigid, but it’s also not very warm either. Transitional dressing can be a bit difficult to tackle—even for fashion people. When I’m in a fashion rut and need outfit inspiration, I love scrolling through the social media feeds of the vast world of online style lovers. I recently took to the internet to do just that. I sought out looks I’d love to try, and I seriously lucked out.

Yes, I stumbled upon a handful of gorgeous outfit ideas that I can’t get out of my mind. Don’t worry. I plan to divulge my findings below. From perfectly oversize looks to styles that utilize expert layering, there are some seriously inspirational ’fits ahead. To top it all off, I did what I do best and scoured the internet for shoppable pieces so you can try out these looks too. Keep scrolling to get closer to the ultimate transitional-weather dressing inspiration.

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Look 1: Oversize Button-Down + Sweater-Vest + Voluminous Skirt
(Image credit: @torivanbreugel)

This look plays with layering, and its use of relaxed pieces helps capture the chic oversize vibe.

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Look 2: Oversize Bomber + Pleated Skirt + Slouchy Socks + Sneakers
(Image credit: @vivian.yrl)

In-between weather can be a bit tricky. This creator makes use of cool- and warm-weather styles in one look to balance things out. 

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Look 3: Co-ord Top and Bottom + Trench + Boots
(Image credit: @giasinatra)

Sets are one of my favorite hacks for putting together a seamless look. For the cool months, opt for knit or jersey fabric and pair it with a thick trench coat and boots. 

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Look 4: Cropped Blazer + Jeans + Skirt
(Image credit: @by.regiina)

Unexpected layering combinations create visual interest and make dressing up so fun. Experiment with layering a skirt over the puddliest jeans. Add a fun cropped jacket or blazer to capture all the creative energy.

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Associate Shopping Editor
Chinazor "Chichi" Offor is a Georgia-born, Los Angeles–based associate editor and model who has recently relocated from Brooklyn, New York, and joined Who What Wear's West Coast offices. For WWW, she utilizes her love of personal style to dish out shopping advice to the masses.After graduating from the University of Georgia's Grady College of Journalism, Chichi moved to Brooklyn and began hustling to make it in the NYC media world. Before landing at WWW, she spent some time at Vice Media Group, where she helped revolutionize Refinery29's plus-size and inclusive fashion coverage and even co-hosted a summer styling series. Prior to R29, she supported Bustle Digital Group's commerce team and freelanced for various publications.Chichi is a multi-passionate, pop culture–obsessed television and music lover who enjoys a good concert and a yummy meal just as much as she loves analyzing cultural trends and throwing together a solid outfit. After work, you can probably find her bopping around the best L.A. restaurants talking about her latest ADHD-fueled hyper-fixation (e.g., Jesse McCartney's underrated career, TikTok black hole discoveries, and theories on the emo-rock music revival).