How to Wear Ankle Boots with Jeans

Want mile-long legs? Pair your black ankle boots (preferably heeled) with skinny jeans. Literally anything else can go on top.

For denim on the looser side: Make sure to show a bit of skin at the ankle and pair them with low, Western-inspired desert booties. The result is relaxed but polished.

The Best Chunky-Heeled Booties Under $100

Yes, the flare-jean struggle is real. Here’s the correct shoe to have peek underneath: a stacked-heel ankle boot. It’ll give you height, while keeping things comfortable.

And for those statement booties that’ll undoubtedly steal the show? That, our friends, is where your trendy cropped flares come in handy. (Or, really, any cropped jeans.)

21 Things to Wear with Your Ankle Boots