5 Ways to Style the Madewell Cali Demi Boot Jeans

I often refer to these as my “weird” jeans, because I find that they’re fairly polarizing and a lot of you out there feel intimidated when it comes to styling them or afraid you can’t pull them off.

That being said, these black ones are possibly my favorite jeans in my whole closet and I wear them multiple times a week! Sizing wise, note that they run big and have a ton of stretch, so I recommend sizing down. Today I want to show you 5 different ways I like to wear them. I’m wearing my Sydney Hoop Earrings in Brass Circle in each look. 

Scroll down for photos and links, or see my IGTV video for more detail on each look! 

Cardigan / Similar tee / Jeans / Loafers

Jacket / Tee / Jeans / Boots / Scarf

Top / Jeans / Mules

Sweater / Jeans / Mules

Jacket / Top / Jeans / Shoes

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  1. 11.21.19
    bananasdontsk8 said:

    Any ideas for styling these in cold weather? Without naked ankles? I have this jean in blue/frayed hem, but I live in Chicago and the season between “too hot for jeans” and “too cold for exposed ankles” came and went in about 2 weeks this fall. I’d like to wear them more this fall/winter, but can’t find any warm enough examples. Help!

    • 12.11.19
      Natalie said:

      The “sock boot” style is really great with these jeans for colder weather!