The First Step

Revamping your wardrobe is a daunting task. It takes a lot of guys a good, long time just to convince themselves it does need to be changed; and once they’re willing to do so, it’s easy to get overwhelmed by all that they have to buy and how they’re going to find it. Most don’t even know where to start and,while there’s no right or wrong answer to that particular conundrum, I recommend starting from the bottom – a man’s shoes.

Most shoes are situation appropriate. Investment bankers shouldn’t wear Vibrams to work any more than an NBA player should wear driving shoes on the court. For the most part, the appropriateness of a given shoe is relatively cut and dry until you get into casual wear.

The casual shoe is arguably the most difficult to wear. Casual meaning going to the movies, grocery shopping, a walk, a fight, the bar, class, the bank or wherever else a man isn’t required to dress up or down. Because there are so many options and because there isn’t a fast rule about what is and isn’t appropriate, it’s easy to make mistakes or just go with what’s easiest.

If you want to start updating your wardrobe to stand out from all the AFC’s out there, start with your shoes. Here’s what you should avoid wearing in most casual situations.

Flip-flops: These are appropriate for the beach, the pool or the spa. That’s pretty much it. I know they’re comfortable and your feet feel liberated but these are not every-day shoes. They look sloppy and lazy and that’s the impression you’ll give off if you’re wearing them anywhere that isn’t close to water. Yes girls can wear them beyond that. No it’s not fair.

Crocs: I hesitate to say that there is ever a time when these are appropriate. However, I know there are certain jobs like working at a hospital or in a kitchen that require a man to be on his feet all day. Don’t ever, ever wear these out in public.


Running shoes/basketball shoes/gym shoes: Jerry Seinfeld was never an icon of style so it’s a shame that this particular look of his has permeated as much of society as it has. Other than flip-flops, this is the most common offender. I’ve seen guys wear these to weddings, church and on dates. They don’t look good on anyone and they won’t look good on you.


Skate shoes: Don’t get me wrong, I have a pair of these that I wear whenever I take my bike out to the skatepark or when I’m going camping. Aesthetically these aren’t nearly as offensive as others on the list. The big problem with skate shoes is they make you look young, and a woman’s hypergamy is going to turn her off to a man who looks like a teenager.

If you look at all of these shoes, the lowest common denominator appears to be two-fold – comfort and affordability. While I can’t make the argument that the more-stylish options will be more affordable, I can tell you they are equally, if not more comfortable.

None of the following options is any more or any less appropriate than the others. Alter them for the time of year and for what it is you plan on doing, but choosing any of these will set you apart from all the other guys in the room.

Chuck Taylors: These are the most casual of the good options. Chucks can be worn by almost anyone in any situation. Because of that, they aren’t going to make you stand out as much, but they will make it look like you have an idea of what you’re doing.

Boat Shoes: Boat shoes are becoming more and more popular lately. They’re perfect in the summer but the darker versions seem to transition well in the fall and spring as well. I recommend more-muted colors in the fall and brighter versions in the spring and summer.

Desert Boots: I just got a pair of these and they’re the perfect balance between formal and casual. They both dress down a suit and dress up a pair of jeans equally well. These are my go-to shoes if I have to wear something to both formal and casual events. As always, darker is a bit more dressy than light.

Loafers: Most loafers look better sockless so these are a warm-weather option. As far as comfort goes, these are going to be your best bet. They’ll fit and feel like your slip-on Vans without making you look like you’re in junior high.

Driving Shoes: I don’t personally own a pair of these but I’ve seen men who do and they wear them quite well. They’re thinner and lighter so you can feel the clutch and pedals beneath your feet when you’re driving, this also makes them great shoes for running to the grocery store or going in to cash a check at the bank. Easy on, easy off.

Bucks: Bucks are where you start to get a bit more out of the ordinary in footwear. At least that’s the case for now. I’ve seen more of these this year than in years previous. They serve the same function as desert boots in that they help dress down formal and dress up casual. The only time I don’t recommend bucks is in the snow. They can be worn with or without socks and come in a variety of colors for both the material of the shoe and the sole.

Brogues: Don’t own a pair of these yet but I’m hoping to. These are perfect for autumn and winter. What sets these apart is how substantial they are. These are the shoes you wear when you’re going to the state fair or traipsing across campus in the fall.

I would say that 99% of men can wear any of the shoes above and make them look good. It’s hard to get these staples wrong and all of them will look good with almost any clothing choice. However, there are some other, more advanced options for those who want to peacock a bit more.

Slippers: I’m not talking about bunny slippers. Slippers means the real deal, the kind of shoes you can only find second-hand or pay top dollar for. Given how thin and delicate they are, these are best worn in good weather and in circumstances that don’t require any real physical effort on your part. These are as dandy as it gets.

Espadrilles: The most common version of these are Toms. If worn wrong, you look like a try-hard hipster and/or completely effeminate. If worn right, these are a great casual shoe for summer that looks more exotic than a pair of Chucks or loafers.

Vintage Sneakers: Again you run the risk of falling into hipster territory with these. I’m personally not a fan, but it is possible to pull off a pair of vintage shoes without looking like you’ve never eaten a steak.

Sandals: I’m planning on trying these out next summer. These are more dressed up and catch more attention than a pair of flip-flops and are also appropriate in more places. It seems to me that the biggest risks are not looking like an Aztec or that you stole them for your woman.