I know a lot of guys go sockless in summer, but I assume there are some rules involved. What are they?

ANSWER:

The sockless look says you’re confident, bold and boyish. It’s a cooler, younger look that’s appropriate practically anywhere except a business setting where a suit is required. Here are a few guidelines for success without socks:

• Let your environment dictate whether or not you wear them. If you’re going to a “serious” event, you should put socks on. It’s possible to get away without them when wearing loafers and pants, but if you’re not sure, err on the side of socks.
• Stick with shoes that are meant to be worn without socks, such as casual shoes without laces, boating shoes and loafers (check out Tod’s for some really classy footwear). You could also go sockless with sneakers in the summer.
• Be conscious of your feet. While you should definitely go sockless with sandals, flip-flops and any other sort of toeless shoe, it can be hard to pull it off if you’re not vigilant about the way your feet look -- so take that into consideration. Also, save sandals for the beach or pool or for weekends when you’re hanging out with friends. Sandals are completely inappropriate for work, and for many other situations as well. Know the dress code before you slip them on.
• Consider your outfit. If you’re wearing linen, denim or khaki pants with a blazer, go ahead and wear a pair of loafers or bucks without the socks. Generally, you shouldn’t wear socks with shorts unless you’re doing sports or going to the gym.

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