What His Shoes Say About Him

Whether they're scruffy, trendy, or practical, what a guy wears on his feet speaks volumes about what's on his mind. To decipher what shoes reveal about a man's personality, we assembled a panel of men's shoe whisperers:  Lloyd Boston, author of "The Style Checklist," and fashion bloggers Sean Santiago (This Fruit Blogs), Thomás Lei (My Belonging), and Brian Sacawa (He Spoke Style). Here's a window into his sole. —By Elise Solé

Slip-on dress shoes

LB: If they're simple and stately, he's a worldly dude. If they're bold and flashy, he may be a player. 
SS: A grown man should be able to tie his own shoes. That's all I'm saying.

Loafers

LB: He knows how to do business and pleasure—sometimes all at once. 
SS: Vintage penny loafers are charmingly bookish; their tasseled cousins say you prefer the weather in Connecticut. 
BS: He either has grown-up tastes or is too lazy to tie his shoes. If you start at his feet and look up, it's easy to tell the difference.

Flip-flops
LB: If you're in a hurry, just know that he's not. Good if you’re into the casual type.
TL: He’s a free spirit who prioritizes comfort. 
BS: Worn poolside with short-cropped swim trunks, he's a man of the world; paired with dirty, frayed jeans, he’s probably still in college. 

Trendy sneakers

LB: Beware of this guy. The trendier the sneaker, the sneakier the man. 
BS: Don't expect gifts from this guy—all his resources go toward making his feet look fabulous. 
TL: He's your go-to guy for the hottest spots in town.

Converse sneakers

LB: Skip him, unless you want Fat Albert's entire gang showing up too. 
BS: In classic black or white, a pair of Chucks says that he was cool before his time. In red, purple, or green, well, that's a different story. 
SS: Four words: He's with the band.


Lace-up dress shoes 
LB: This is the leveling device of all shoes, but they could indicate low levels of desire in a guy.
BS: In the words of ZZ Top, "Every girl's crazy 'bout a sharp dressed man." A guy who rocks a great pair of lace-ups likes to look good and usually does.

Sandals

LB: He's a nice guy but he resists modernity. And if he pairs them with socks, run (don't walk) to the nearest exit. 
BS: Sandals walk a fine line between nonchalance and indifference. Though if he's wearing them with socks, it's likely the latter. 

Running sneakers

LB: If they're worn with running clothes, cool. If he's wearing them with jeans, even cooler. 
TL: A guy who lives for casual Fridays. Proceed with caution. 
BS: Worn at the gym, he's a practical guy. Worn with a suit, he's getting passed over for that promotion (again).