Readers Ask: Dear Lucky

Q: I have these awesome brown suede Jil Sander desert boots. What on God's green earth do you wear with desert boots? Anything long makes me look like a polygamist, and anything short makes me look like a wannabe hipster.

Illustration by Lauren Friedman

A: The desert boot holds a special, wear-it-with-anything place in my heart: I lived in Italy during a moment when its entire population was consumed with a craze for desert boots. I mean every man, woman and child had a pair, and wore them every day. I once sat down in the middle of a crowded piazza and every direction I looked, a sea of desert boots. Literally I was the only person in the entire piazza un-desert-booted.

Here in America, however, this fall, I think the wild sexiness of the shorts-plus-desert-boot combo overrides any wannabe-hipster aspect. Do it, do it, do it! Short, short, short! It's so sexy. A short skirt or actual shorts are equally good; wear with tights (black, tan, gray, whatever you like, but your legs will look longer the closer the tights' shade is to the boots!). If the weather permits, go bare-legged. Your other option is skinny jeans/pants. They should be short enough—not capri but definitely not so long that they touch the shoe—so it's clear you're featuring the boots.

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