This year’s trend of baggy aesthetic outfits has intrigued me. For so long we were told that the best outfit formula was: baggy on top and tight on the bottom, or vice-versa. But this year’s proportions have tended toward baggy on both the bottom AND the top. Many of us millenials and Gen-Xers are just not sure how to pull this style off without looking sloppy.
This post is here to give you tons of inspiration and ideas about the best ways to style your baggy outfits in the most aesthetic way possible. Be prepared to be both ultra cool AND ultra comfortable as we transition into fall with our baggy (yet still feminine and attractive) outfits.
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Baggy Aesthetic Outfits
The baggy aesthetic outfit trend seems to have migrated to high fashion from street style and the recent surge of “baddie” aesthetic. If you are unsure of what the term baddie means- well, think about the word badass. It refers to someone who is confident and stylish and has a little edginess. She doesn’t care what anyone thinks of her and she dresses for herself. While baddie style borrows some elements from men’s fashion, it creates a feminine look that anyone can achieve with a bit of intention and forethought. Many baddie-style outfits feature baggy or wide-leg pants, bringing comfort and style together. These are a nod to the wide-leg pants trend of this year that has evolved as a kind of backlash against the years of constricting skinny jeans that we all subjected ourselves to.
The wave of wide-legged pants popularity has grown to include baggy pants, and as a child of the 1990s skater culture, I am all for it. We are taking our style cues from the Scandi girlies and from the street style of Billie Eilish, and we are loving it!
Scandinavian Baggy Outfit Inspo:
Our starting point for the baggy aesthetic is the iconic style of Scandinavian girls, who have been rocking the baggy trend for years. From baggy trousers and chunky sneakers worn with an oversized sweatshirt or handknit sweater, these fashionistas are the masters of the oversized outfit. And they make it look sexy!

All images via Pinterest.
Scandinavian fashion embraces baggy clothes, showing a shift from its minimalist, function-focused roots to a more relaxed, contemporary style. Scandinavian women have always loved that minimal, practical vibe, and somehow oversized outfits fit right into their aesthetic. The best things about these loose silhouettes? They’re all about comfort and flexibility while still looking effortlessly cool. They also make it easy for layering during the colder months. Another thing to love is how baggy clothing taps into the whole gender-neutral fashion trend- while still looking feminine and edgy.
Extra Oversized Denim Jackets
One of our favorite trends this year is the ultra oversized denim jacket. Denim jackets have been a staple in our closets forever, but this is a fresh new way to wear them and we love it. This is a great transitional style that can carry you from late summer into fall if you wear your jacket with shorts. And for colder months or locales, there is plenty of room underneath to layer a wool or cashmere sweater.

To take this look to the absolute coolest limit, get yourself a pair of 90s-inspired brogues or chunky black loafers, and wear them with socks, as seen below.
Baggy Jeans with an Oversized Flannel
For a super casual and ultra cool look, wear your baggy jeans with an oversized flannel. This combination of grunge and street style is perfect for autumn and winter errands and school days. Balance out the larger proportions of this outfit with chunky sneakers- or even better, doc martens or combat boots. Platform sneaks or boots would also be an ideal footwear choice.

Baggy Outfits + Black Leather Jacket = Instant Cool-Girl Style

We are especially enamored with the oversized black leather jacket, a classic throwback from the ’90s. When paired with equally loose-fitting tops and a pair of baggy jeans, this is an equation that just looks cool AF. Wear an oversized jacket over an oversized blouse, wide-leg pants, and a pair of sneakers or chunky boots for a winning combination.

We also love the option of a shearling-lined leather jacket worn with baggy jeans and a pair of classic white converse.
Baggy Cargo Pants + Oversized Hoodie or Sweater
This is a clear Y2K throwback and we are loving it. Baggy cargo pants look just as cute with sneakers as they do with combat boots. For the easiest outfit equation just pair with a baggy hooded sweatshirt or an oversized sweater. Is it giving Baddie Kim Possible? Maybe a little, but we are here for it.
Baggy Bottoms + Baby Tees
If you aren’t quite ready to go full-on baggy with all of your outfit components, never fear. You can ease into the trend by wearing a pair of boyfriend, baggy or wide-leg jeans with a slimmer fitting top like a baby tee. It will give you enough shape to flatter your figure while still allowing you to embrace the baggy outfit aesthetic. You don’t need to throw yourself fully into any trend unless you feel comfortable! Cropped or slim-fitting tops might be a more palatable outfit combo for many of us, especially those of us still struggling to let go of skinny jeans, ankle booties, and tight leggings.
The appeal of baggy clothing lies in it’s comfort, but there’s more to the appeal. It’s also a social statement that rejects the idea that women’s clothing should be form-fitting and traditionally femme in order to be sexy. There is an edginess in the contrast between the shape of the body and the loose clothing that is truly alluring. The slicked-back hairstyles and smaller sunglasses of the moment contribute to the visual impact of these baggy outfits. It’s a rejection of the traditional wisdom of dressing. The proportions that many of us are used to have changed.
The Impact of Street Style
Street style fashion has significantly shaped the rise of baggy clothing among young, fashion-conscious women, as it reflects broader social movements and changing attitudes towards self-expression. Baggy clothes have become a symbol of freedom and body positivity. They offer a way to challenge traditional beauty standards that often emphasize form-fitting silhouettes. These oversized styles provide a sense of comfort and confidence, allowing them to hide insecurities while still looking stylish. Rooted in youth culture, streetwear has blurred the line between casual and high fashion. The baggy aesthetic’s subversive, inclusive nature has resonated strongly, making it more than just a fashion statement. it’s become a form of empowerment for many young people today.