25 Pretty Shoes That Will Look Perfect With Every Pair of Jeans You Own

Listen. I take no pleasure in twirling out a clichéd phrase like "shoes make the man.” But tired, gendered connotations aside, the saying holds a kernel of truth: My shoe choice helps me tap into different sides of my style and personality. As an actress, I know that slipping on a specific pair of shoes can inform my choices. I’ve thrown on shockingly high heels (even if they stay out of frame) to help me lock into a character. What I put on my feet quite literally affects the pep in my step that day.

But anything that has the power to giveth can also taketh away. If you’ve ever stepped out of the house feeling invincible in a new pair of jeans, only to be brought down a peg when you catch a glimpse of your feet in a passing mirror, you know that the wrong footwear can undo an otherwise flawless ’fit. Volume, shape, and length come into play when toeing that delicate shoe-pant line.

I'm in a particularly giving mood this holiday season, so let my errors be your education. I’ve broken down five pairings so you’re never caught with your metaphorical pants around your ankles (unless they’re ankle cropped, which would look great with a pair of flats). Keep reading!

BAGGY + BALLET

A playful take on proportion. Puddle jeans look surprisingly sweet with a dainty ballet slipper peeking out.

WIDE LEGS, POINTY TOES

Bring the extreme volume of a wide leg into balance with an angular, pointed toe. 

BOOTCUT MEETS BOOT

Hey, it's in the name. I don't make the rules! 

But in all seriousness, the slightly flared opening of these jeans hangs nicely over the slim profile of a boot, showing off just enough to warrant some pattern or texture.

STRAIGHT LEG + SANDALS

Straight-leg ’90s-supermodel denim, a fresh pedi, and strappy sandals make for a flirty date-night trifecta. 

CROPPED + STATEMENT

If you're gonna show off those gorgeous ankles, really give 'em a show with sculptural heels, iridescent embellishments, and sky-high height.