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.

more on luckymag.com

The Perfect: A Statement Watch For Every Style

Elegant but edgy, Hermès’ studded, flip-face design is our favorite way to stay punctual.

15 Celeb Hairstylists, Makeup Artists And Nail Pros To Follow On Instagram

No FOMO here: these glam squads' Instagrams are so good, they'll almost make you feel like you're getting ready for the red carpet with the celebs.

The Fall Shoe Guide: Plaid Low Tops

A little bit punk, a little bit prep—your favorite weekend-ready shoes get the tartan treatment.

Hair How-To: Eight Ways To Upgrade Your Bun

Pretty twists spotted on this year's runway put a couture spin on the go-to bun.

The 15 VMA Nominees That You Need To Follow On Instagram

Long hours on the tour bus and crazy music video costumes means musicians are the best people to follow on Instagram.