Which Shoes Go With Your Pants

I think I’ve touched on this before, but I’ve always had a thing about wearing wide-leg pants with closed toe shoes. In my mind, wide-leg only goes with sandals, or pointy-toe pumps. I realized though that I also have other mental “rules” about which shoes with which pants (or hemlines, the skirt edition is coming later this week or early next week), and those rules, or preferences, make it easy for me to decide which shoes “go” with what I’m wearing. It’s more or less intuitive for me, but this week I hoped to better articulate that intuition, and share some of the reasons why I choose which shoe with which pair of pants.

And I didn’t want to go nuts pulling out all my shoes and showing eight million options, so I pulled together what I think makes the most essential shoe “wardrobe” - the basic categories that I need to have covered in my arsenal to make getting dressed easier.

The bulk of this info is in the video above - I’m trying something new where I put the intel there (and make the video much shorter) and then in the body of the email put the outfit photos with credits and links. It’s a lot to digest with a video and then basically reading the whole thing out again in the body of the email, but let me know what you think.

Here we go:

DIFFICULTY LEVEL 0: Cropped kick flares (these are High Sport) go with basically any style shoe - I like them best with loafers - something that mimics the structure of the pants, and feels substantial, but honestly anything basically goes here. The loafers are by The Row (these are also really good and under $200), this blazer is from Jamie Haller, the plaid shirt was thrifted (but here’s a good one, and then here is maybe the best one of all time), and the yellow tee is from Still Here, and it’s one of my favorite things I have.

DIFFICULTY LEVEL 1: For a cropped, straight leg jean, I still think that you kind of can’t go wrong - with the exception of ankle boots where the shaft is a lot wider than your ankle/leg. I go into it a lot more in the video, but that’s a no-go, otherwise, depending on what you’re doing and what the weather is like, basically every other shoe in your wardrobe is fair game. Keeping the top part of your foot, or your toes exposed, however, really does a lot to elongate your leg. I show the difference in the video, but I usually like to have some part of my foot/ankle/toe exposed when wearing cropped pants. I’m wearing a Sezane coat, a Kule sweater, a Pucci scarf, my Wrangler jeans, and Ann Mashburn flats. Also, these pearls I’ve been wearing are vintage, but try these, these, these (oh, baby) or these if you’re feeling silly - or this for a pearl that’s not such a LOOK.