The Closet Coach

Although I usually focus on women’s clothing, this week my advice is for the gentlemen.

Jonathan F. wants to find some casual men’s shoes that he can wear with jeans so he can keep his running shoes for the athletic pursuits for which they are intended. He tends toward the classic and conservative, so no neon high-tops for him.

Options for Casual Men’s Shoes

Here are some styles that will work for him:

• Lacoste Bateau: A variation on the classic boat shoe, this one comes in several colors and is perfect for the preppier wardrobe. Think chinos and linen pants. $75.
• Converse Jack Purcell CP: Also a variation on a classic style, this time the iconic Converse low-tops. Every man’s wardrobe should have a pair of black Converse, whether Chuck Taylor All-Stars or Jack Purcells (and Levi’s 501s, too). $55.
• PUMA Basket II: From Puma’s archives, this 1971 style still looks modern. The black/white and white/white combinations can be worn with just about anything. $60.
• Onitsuka Tiger by Asics – Mexico 66: Although they’re based on a version that was worn at the 1966 Mexico City Olympics, these Asics come in a wide variety of color combinations that take them from subtle to Hipster Approved. $80.
• Vans – Authentic: Speaking of shoes first seen in the ’60s, these sneakers first gained popularity with surfers and skaters (Jeff Spicoli in “Fast Times,” anyone?) and still look cool today. Show them you haven’t lost your style by getting a checkerboard pair. For ultimate ease, pick up the slip-on version. Best of all, they’re only $42.

As you can see, this list focuses primarily on sneakers, since those are the kind of shoes Jonathan is looking to replace. But equally viable options include the original leather boat shoe, the Top-Sider from Sperry ($65), or a pair of ankle-high chukka boots. To go really high end, might I suggest these Ebono chukkas from Bruno Magli? ($285)

Wearing and Caring for Casual Men’s Shoes

In all cases, here are some tips for selecting and caring for casual men’s shoes:

• Consider your wardrobe. If you favor concert T’s and hipster jeans, boat shoes are probably not the choice for you. Think Vans or even Doc Martens.
• Keep them clean. If they’re leather, keep them polished. If they’re canvas, toss them in the wash from time to time, or give them a surface scrub with soap and water.
• Choose the right socks. If you’re wearing pants, they can match the color of your pants or the color of your shoes, but no white socks with dark shoes ever. And if you’re wearing shorts, please keep them short or folded down. Unless you’re Wilt Chamberlain time traveling from 1977, you should not be wearing knee-high athletic socks with your sneakers and shorts.
• No Crocs. Maybe when gardening or performing surgery, but never at Home Depot.
• Flip flops are for the beach. No-one wants to see your toes unless you are traversing sand or a boardwalk. If you must indulge in mandals (man sandals) for summer wear, make sure they are closed-toed.

Now it’s your turn: What are your favorite casual men’s shoe styles? What are the absolute no-no’s?

[In addition to the styles noted above, About.com also has a good guide to Men's Shoes to Wear With Jeans, which includes some classic tennis shoes, as well as boots and loafers.]

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