Everybody knows that guy. Hopefully you aren’t that guy, but it feels like there’s one guy in every group of friends who never has the right thing to wear. He shows up to weddings in a polo shirt, tries to go hiking in old skating shoes, and wears white tube socks no matter where he’s going.
It’s not always that he’s a slob. A lot of the time he’s just never had anyone walk him through what to buy so he can have the right clothes for each occasion. It can be intimidating walking into a store with no idea what to buy, especially if it’s a high-end store.
As intimidating as buying new shirts or socks can be, it’s probably even more intimidating for a guy to figure out which shoes to buy once he graduates college and realizes he needs to leave his days of wearing nothing but flip-flops and athletic shoes behind him.
There’s no need to fear, though. Buying adult shoes isn’t as bad as it may feel. You just have to buy a new pair here and there until you’re prepared for any situation.
First, though, while it’s time to stop wearing athletic shoes everywhere, they’re still important for working out and playing sports. A good pair of cross trainers will be fine for going to the gym, the occasional jog, a little weekend basketball, and some recreational hiking. If you end up getting seriously into running or CrossFit, you’ll need to buy more specialized shoes, but as long as you aren’t doing anything too hardcore, one pair should be fine.
You’ll also want some good looking shoes for walking around and wearing on regular basis. Boat shoes have been a popular choice with guys for this purpose lately, but I actually recommend a pair of drivers instead. You can wear them in all kinds of situations like you can boat shoes, but they’re a little bit more stylish, which means you won’t look like just another guy wearing Sperrys like his dad.
It’s also a good idea to pick up a pair of penny loafers. They’re classic, versatile, and will class up what any guy is wearing. You can wear your loafers in a lot of situations you could still wear your drivers, but they’re also a good way to look a little bit dressier on a special occasion.
Loafers will also work with a casual suit, but if you work in a professional environment, you’ll want to pick up a pair of oxfords. They’re too formal to wear with jeans, but you’ll look great wearing them with your suit whether you’re at work or at dinner for a special occasion.
As long as you stay in the city, those four pairs of shoes should keep you prepared for the vast majority of situations. You may end up needing a pair of tuxedo shoes, but as rare as tuxedos are becoming these days, it’s doubtful. This list is also not exhaustive, and as you decide to expand your collection, there are quite a few other options to choose from that aren’t included.
Unless you plan on never leaving the city or doing any yard work or manual labor, I do, however, recommend filling out your collection with a good pair of work boots. You don’t need to buy anything too fancy, but keeping some Wellington boots on hand will be great for those times you need to get some real work done. They’re more sturdy than athletic shoes, so while you may not wear them to mow your lawn, they’re perfect for any time you’re landscaping your yard, hauling brush, camping, fishing, etc.
Looking at all the different kinds of shoes for sale in a store can definitely be intimidating if you don’t know exactly what you’re looking for, but if you break it down and head out looking for one of these five shoes, it’s a lot easier to narrow your options down. Pretty quickly, you’ll have a small collection going and will be ready to wear the right shoes no matter what the occasion.