Classic staples have gotten the oversize treatment over the last few seasons. Blazers have gotten looser and longer, shirting is roomier, and even jeans are baggier. This more relaxed aesthetic certainly may seem controversial for some—especially when an entire silhouette is made up of more oversize items with the proportions feeling different. For me, it’s all I want to wear now. As someone that used to live in skinny jeans paired with more fitted tops and has recently ventured into looser denim, this new vibe just feels fresh and forward to me.
When I slip into my favorite oversize shirt and baggy jeans, I feel like I’m stepping out in a very relevant and cool outfit. On that note, I have a plethora of ensembles saved on IG that I’m interested in testing out this season and/or to keep in the back of my mind to suggest to others when they ask for chic outfit ideas. I thought I’d round up a few of the standout looks in case you’re looking to test out the oversize look as well. Keep scrolling for more, complete with a smattering of shopping picks to inspire your further.
This is one outfit I’m 100% going for soon with the relaxed white shirt, oversize blazer, and loose jeans. The sneakers add a nice touch.
I don’t have a pastel oversize shirt yet, but I want to buy one soon to wear with my favorite jeans and chic accessories.
This ensemble is so effortlessly chic with the trench coat, coordinating pants, and cool Converse sneakers.
Relaxed, tailored shorts with a tucked-in white blouse is quite polished for summer.
A denim shirt is quite fresh with loose trousers for the season. A baseball cap adds a relaxed feel as well.
Next, check out more easy outfit ideas.
-
It's Here: The It-Girl Way to Wear a Sweater in 2025Kendall Jenner just solidified it.
-
Cooler Than a Trench—This Coat Trend Is Quietly Taking Over for FallRich b*tch vibes.
-
Sorry to the Black Pieces in My Closet—I'm Obsessed With This Equally Chic, Classic Color for FallFashion people from London to Paris agree.
-
Cooler Than Leggings—Everyone With Good Taste Is Wearing This Casual Outfit Combo This FallCount us in.
-
Suddenly, Everyone With Good Taste Is Styling Their Fall Outfits With This Shoe TrendSee the proof inside.
-
This Dated Denim Pairing Is Suddenly the Chicest Way to Wear Jeans for Fall 2025Easy and stylish.
-
The Specific Way Everyone Stylish in NYC Will Be Wearing Boots With Jeans This FallIt's all about this styling trick.
-
I'm an NYC-Based Dad Who Is Always on the Move—This Is How I Redefined My Everyday WearEffortless, easy, and cool.
