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

News Flash: Karlie Kloss' Latest Victoria's Secret Ads Are Red Hot—Literally

We see the supermodel sporting a super-blonde 'do and an assortment of festive red, coral and pink lingerie. Happy Friday, indeed.

Five New Curling Irons That Make It Easy To Create Perfect Waves Every Time

These waving wands do all the work for you.

Ridiculously Good Riding Boots At Every Price

Whatever your budget may be, we've found a great riding boot to fit it. Click through to shop our picks now!

From Cheetos To Pegacorns: 27 Of 2014's Wildest, Most Extravagant Celebrity Halloween Costumes

From Taylor Swift's "pegacorn" to Katy Perry's Flamin' Hot Cheeto, celebrities are on their A-game this Halloween. Click to see our favorite costumes…

The Lucky Style Collective: Happy Halloweekend!

Our favorite style bloggers teach us a thing or two on how to gear up for an epic Halloween weekend!