Ankle boots are the latte of footwear: They're sophisticated, great any time of year, and an all-around crowd-pleaser. In fact, we're fairly sure, if we were forced to play favorites with our footwear, it's booties that would take top spot. Still, as we grow older, the outfit we want to wear with the shoes shifts. In our 20s, maybe it was a minidress and statement boots that spoke to us, but over time, it's more-sophisticated styles that catch our attention.

Inspired by trendsetters in their 20s, 30s, 40s, 50s, and 60s, we're showing off ultra-flattering outfits to wear with ankle booties for every decade. Consider this a guide to rocking the go-to shoes at every age. But no matter the year on your driver's license, feel free to choose whichever look feels right to you. At the end of the day, it's about what makes you feel best, whatever your age may be.

Check out the styles, along with shopping inspired by each, below!

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