Five Ways to Wear Wide Leg Jeans for Fall and Winter

When I asked my followers what they wanted to see for fall content, a large request was for ways to wear wide leg jeans (and shoes to wear with them).

Here are five wide leg jean outfits with five different shoe options. To be clear, I am styling ONE pair of jeans, with different tops, shoes, & accessories! I like to maximize my wardrobe & style things multiple ways, so one pair of wide leg jeans is what I have here.

My jeans are almost sold out in this wash (they’re Levi’s ribcage  “she’s a cutie” wash, but there’s lots of other washes available!) so I did my best to try & find and link some wide leg jeans that are similar.

If you prefer video content, you can see the reel HERE and where I talk about the shoes HERE.

All items (or similar if it’s an older piece—it’s always noted in the L T K description if it’s not exact) will be linked beneath each photo. I use affiliate links, meaning I earn a small commission if you make a purchase through them. There’s no extra cost to you, and your support helps me continue creating content like this. Thank you!☺️

A heeled clog (or mule!) is always a cute option with wide leg jeans! I paired a button front cardigan and high neck tank with my wide leg jeans for this look.

Outfit linked HERE.

This is a new option for me as far as shoes go, but a flat (and specifically in this outfit, a Mary Jane flat) can look really great with wide leg jeans. I fonished the look with a long black duster cardigan and high neck tank.

Outfit linked HERE.

Loafers are also a new pairing with wide leg jeans for me, but I think they look wonderful! I especially love matching my top to my shoes (an “outfit sandwich”) and also adding a matching bag! A turtleneck is a favorite look of mine with wide leg jeans.

Outfit linked HERE.

A classic heeled boot is a no brainer with wide leg jeans. It always looks classy! I added a white gauzy button up, silk scarf, and matching bag to complete the look.

Outfit linked HERE.

Chelsea boots are one that I haven’t always paired with wide legs, but I feel like it’s really cute AND functional (especially in winter!). To finish this outfit, I added a cropped sweater, black denim jacket, and matching bag (I also forgot to take a photo of this look, so screenshots had to do!).

Outfit linked HERE.

11 Comments

  1. Thank you, I love this! I just got a pair of wide leg jeans; way more comfy that skinny jeans! and I needed to see ideas of what shoes to wear with them for fall. I would not wear the cuffed style because my legs are on the short side; I hem instead of cuff to visually elongate. You look great in all the pics

  2. You really look very untidy and lazy to hem the jeans that is obviously too long ,I would never wear it like you,I am very classy .Not impressed.

  3. I love wide leg jeans, but there is nothing attractive about this new cuffed look that’s trending. It’s like they just git too lazy to cut the pants off and hem them.

  4. That is not actually wearing the wide leg jeans any different.. That is wearing a different top, shirt or sweater with them the jeans have not changed.

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