Baggy jeans aren’t a new trend by any means, but rather they’re an old favorite silhouette that’s making its way through modern fashion again. Whether you wore these back in the 90s and aren’t sure how to make them work for today, or are new to the style and are feeling unsure about what to pair with them, I’ve got your back.

Similar trench / similar tee / jeans (sized down) / sneakers / bag / sunglasses

This is the outfit that I was actually wearing for the day — it’s simple, comfortable, and a bit boyish. I loved it!

Duster cardigan / tank (Natalie15 for first order) / jeans / necklace / boots (15BORTON for first order) / sunglasses / sling bag

I wanted to challenge myself to style these with boots for cool or rainy days, and I really love how these mink-color boots looked! To keep it more tonal, I went with a white tank (if it’s really cold you could do a fitted white long sleeve) and a cozy duster cardigan. I finished things off with my Gardenia-colored sling bag.

Blazer / tank / jeans / low heels (15BORTON on your first order) / necklace / black bag (old) and bag chain / sunglasses 

This one was sort of cheating, as I wore this out to dinner over the weekend! I double rolled the jeans and love the mix of feminine and masculine elements.

Cardigan / jeans / ballet flats (15BORTON for first order) / similar bag and bag chain

This is a “loose/loose” mix of things that is very comfortable. Everything is oversized, but the proportions still feel good since the cardigan is cropped.

Similar trench / button down shirt / jeans / ballet flats (15BORTON for first order) / bag / similar sweater / sunglasses

I really love the look of these baggy jeans with a long trench coat, and this look is no exception. I kept it pretty classic with a button down shirt and ballet flats.

Similar sweater / ballet flats (15BORTON for first order) / bag / sunglasses

Here’s another oversized combo — a slouchy sweater and baggy jeans is peak comfort!! The front tuck adds some shape to the look, and the ballet flats give a feminine touch.

Blazer / tank (NATALIE15 for your first order) / jeans / similar slingbacks (same brand) / bag / sunglasses 

Here’s a look that would work for a casual work environment, or for going out. The bag adds a nice touch of pattern to an otherwise very minimalist look.

Similar jacket / tank (NATALIE15 for your first order) / striped shirt / jeans / high tops

This one feels like a bit of a throwback with my old field jacket and classic Converse. Field jackets are back, and I’m so happy about it because I am a sucker for military green!

Vintage coat (current similar option) / tank (NATALIE15 for your first order) / striped shirt / jeans / high tops / sunglasses

Here’s the same look as the last one, but with a long coat swapped in for the field jacket — I will be wearing this one a lot when it finally gets cold out here!