Rihanna Knows What to Wear to Make Baggy Jeans Look Chic

If you're one of the many who have ditched your skinny jeans in favor of baggy ones, welcome to the other side. And if you're wondering, Now what? just ask Rihanna. What to wear with baggy jeans can honestly be a bit of a head-scratcher. They can easily look sloppy, but if you prefer to look more polished when wearing them, there's a way, and Rihanna just nailed it while heading out to dinner in NYC.
With her baggy, ripped jeans, Rihanna wore a structured, oversize blazer and square-toe loafers. By opting for sophisticated pieces with the jeans, she struck the perfect cool-chic balance. Her look can easily be replicated just by pairing any structured oversized blazer you own and loafers or other polished shoes. You can't go wrong with this combination—mark my words.
If you just found your new favorite baggy jeans outfit, you can thank Rihanna and scroll to shop the pieces needed to create this chic look.
On Rihanna: Gucci Red Leather Jacket ($4192) and jeans; Bottega Veneta Croc-Effect Leather Loafers ($1050)
Shop Blazers
Shop Loafers
Shop Baggy Jeans
Next up, the best jeans-and-shoes pairings for spring and summer.

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater arts. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.
-
If a NYC Fashion Person Were Scrolling Through Amazon, They'd Buy These 27 Basics
The best 2025 Amazon basics.
-
Of Course, 2025's Cali Summer Uniform Involves This Timeless Denim Trend
Can you take any guesses?
-
Red Who? Sorry, But Cool Fashion People Are Only Interested in Wearing Jeans With *This* Sneaker Color
It's the new red (and yellow, green, and silver).
-
I Found It: The Only Denim Trend That Makes Flip-Flops Look Sophisticated Instead of Cheap
In Kendall Jenner we trust.
-
This Summer Denim Trend Is the Opposite of Skinny Jeans, and I'm Seeing It Everywhere
Your outfits will look chic with this silhouette.
-
Olivia Munn Just Wore the Only Denim Trend That Could Disrupt Skinny Jeans' Resurgence
Elegance personified.
-
Linen Pants! Full Skirts! Long Shorts! Zara Has Every Single Chic Bottoms Trend—40 Picks That Are Worth Your Attention
Good luck picking just one.
-
Not Skinny, Not Wide-Leg—the Specific Denim Trend Frequent Flyers Always Wear to the Airport With Sneakers
"Just right" jeans.