There’s an insurance company that advertises heavily in Seattle, using caricatures of local stereotypes. One of those is “Sandals With Socks Guy.” Yes, the city where I live has enough guys walking around wearing Tevas with white tube socks that an insurance company feels comfortable making fun of it. And a quick survey of the casual neighborhood watering holes shows that in warmer weather, your average twenty-to-thirty-something does feel that sandals (even flip-flops) are acceptable to wear out. (Maybe if we were a beach town and they were blending in with the surfers, but we’re not and they can’t.)

Paging Huggy Bear.
Paging Huggy Bear.

Many of these guys are single, and will likely remain so.

Here’s a secret: on occasion, you can get away with jeans, a t-shirt or even a polo, but women actually seem to care about your footwear. I’ve seen this with my own eyes: a guy sits down next to a gorgeous woman and begins chatting her up. She’s smiling, she’s tossing her hair, she’s leaning in…and then she finally gets a glimpse below his knees and immediately begins closing up her body language. Suddenly she remembers she has a boyfriend and moves away. But hey, dude’s feet are comfy!

Even your Air Jordans are problematic – besides their date-inhibiting nature, most clubs impose a strict no-sneakers dress code, designed to keep out the gangsta wannabes and people who can’t afford the drinks. So save ’em for the court.

The good news is that there is a whole world of options that offer both style and comfort. (Don’t worry, you can still wear your Tevas around the house or at the park. But please, not with socks.) Ideally, you should have three or four pairs of shoes for different occasions, but you can get away with as little as one if you shop carefully.

Simple kicks

For a basic walking-around-town shoe you can wear with jeans or chinos, casual footwear companies like Skechers and Converse make a huge line of items that aren’t really sneakers yet aren’t dress shoes. They make both standard lace-up “oxfords” and slip-ons, from loafers to pseudo-sneakers, all with comfort in mind.

As far as color, you can wear just about any color shoes with good blue jeans. Just make sure that if you wear a belt with black or brown shoes, the color matches. If you’re going to go more bold with something like a red or blue shoe or a pair of Eddie Van Halen-designed Vans, a black belt will suffice.

Club feet

Sometimes even red suede dress sneaks are going to challenge the dress code at a lot of clubs. Also, if you plan to be dancing you don’t want shoes designed to stick tenaciously to the ground. If you’re going for comfort, the baseline would be driving shoes (“moccasins”) or loafers.

However, if you’re going to stand out in that club crowd an even better choice is a boot. There are some awesome boots out there that will go with jeans, chinos and dressier pants. I pretty much go exclusively with boots when I’m dressing for a night out – I’ve got several pairs, including a pair of natural snakeskin slip-ons and another pair made from cowhide with the cow’s hair still on it.

The most versatile shoe is probably the loafer – you can wear it to work and then out on the town. There are versions with tassels and others with buckles, suede and patent leather. And if you buy something like this Rockport Dureau, it’s also going to be super-comfortable: Rockport specializes in shoes that look dressy and feel incredible.

Shoe basics

In fact, guys are really lucky: no doubt you’ve heard women complain about how their feet go numb by the end of the night in their $300 shoes. Men simply refuse to wear shoes that aren’t comfy, and the manufacturers listen. My most expensive pairs of shoes also happen to be my most comfortable.

You’ll likely notice a more significant difference between a well-made (and usually more expensive) shoe and a cheap one than in any other article of clothing. Cheaper shoes will also wear out much faster than good shoes: stitching and stress points get more attention from a good shoemaker. So does the footbed where the arch support and heel padding live.

Often you need to see, feel and wear the shoe to really tell how it will fit and wear, so I strongly recommend making a field trip to some local shoe stores so that you can see the differences between brands and styles. You can buy online, but make sure the store has a solid return policy – sometimes shoes run larger or smaller than the size on the box. And wear the kind of pants you’ll primarily wear with the shoes, so you get a better idea of how they fit in your wardrobe.

I hope this gives you some direction. Experiment and try on various types of shoes, and as always have fun with it. In another post I’ll show you some of my kicks.

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