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Details make the difference between a look and a great look. Thus, the loose silhouette of baggy jeans can be used to style brown slouchy boots differently by tucking the hem into the shoes. The pairing achieves just the right touch of casualness, which can be complemented by anything from a chunky sweater to a long wool coat.

Isabel Marant Dalby Tasseled Leather-Trimmed Suede Ankle Boots

Levi’s Premium Baggy Dad Barrel Jeans

Baggy denim-on-denim with boots

As seen in Paris .

As seen in Paris .

Daniel Zuchnik/Getty Images

As seen in Paris.

As seen in Paris.

Valentina Frugiuele/Getty Images

Creativity is everything when it comes to styling, especially when it comes to basic garments, such as oversized shirts. Styling a button up with a denim jacket creates a distinctive image when you let the sleeves or collar show. Adding a pair of baggy jeans and and boots will be the route to go for an elevated look.

Gap Low Slung Extra Baggy Jeans

We The Free Opal Swing Denim Jacket

Baggy jeans with brown boots and a blazer

As seein in Paris.

As seein in Paris.

Edward Berthelot/Getty Images

As seeon on Anne Hathaway on July 25 2025.

As seeon on Anne Hathaway on July 25, 2025.

TheStewartofNY

One of the best ways to embrace the new season is with a color palette that favors earthy tones. This can be achieved with accessories like headbands and scarves, or with outerwear and boots. For the latter, try pairing a light blouse with a blazer and brown boots.

Old Navy Kitten Heel Booties

Baggy jeans and boots with a plaid shirt

As seen in Munich.

As seen in Munich.

Moritz Scholz/Getty Images

The most casual look on this list comes with baggy jeans and grunge boots. As proof that retro fashion is still very much in vogue with the change of season, it’s best to take inspiration from the ’90s when styling these two pieces. Therefore, a plaid shirt worn around the waist is a must.

Polo Ralph Lauren Relaxed-Fit Plaid Cotton Shirt

Baggy jeans with boots and a striped top.

As seen in Berlin.

As seen in Berlin.

Jeremy Moeller/Getty Images



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