Back to School: The Kicks

One of the most important things a man can do to up his style game is to get a decent pair of shoes and today I’m going to outline some good, casual shoe options for the young guy heading back to school. This post is going to have a lot of different options so you can find something regardless of what your personal taste is. At the same time, we’ll stick with classics within those options so you don’t look back and regret buying something too trendy Let’s start more casual and work our way up from there.


You don’t get much more classic than Vans. These things have been around forever and there are plenty of options to choose from. There’s been a revitalization with the classic styles instead of just the skate/BMX shoes they were pushing so hard a few years ago. I can recommend these for guys who are still in high school, or college men who find themselves in the most casual of situations. These are what you want to wear when everyone else rolls into class in flip-flops and sweatpants. You won’t be overdressed, but you’ll still be a step above everyone else.

Chuck Taylors

You saw the Sandlot right? These were ubiquitous in the 50’s and 60’s. They were the original athletic shoe and are still worn by style-conscious athletes today. Just like the Vans above, Chucks come in multiple colors. However, I recommend you stick with white or grey. Anything else is going to look too Hot Topic.


Jack Purcells

A bit more dressed up than the Chuck Tailors, these are the classic white sneaker that will look good on almost any guy during any time frame. They are the wayfarer’s of shoes in that they are never extremely catchy or fashionable, but they are never out of style either. Going with the all-white option is a bit prohibitive in that you really shouldn’t wear them after the weather starts to turn, but through most of the US you can wear these from March through October with no real problems. Wear them sockless with shorts while you’re getting back into the swing of things, or even with wool trousers to get the High/Low effect in class.

Chukkas/Desert Boots

This is where we start to get a bit dressier. Desert boots are acceptable wear on casual Fridays in a business environment, but they still fall into the casual side of things. Aesthetically speaking, there isn’t a shoe more autumn appropriate than a pair of chukkas. The other benefit to these is they’ll wear a lot further into winter than the other shoes on this list because they’re actual boots. Chukkas come in both suede and traditional leathers but the suede looks much more casual therefore, for anyone going back to school, I’d recommend sticking with suede.


There are few articles of clothing that get to be High/Low in and of themselves, but bucks are one of them. These are dress shoes that look better the more beat up they are. You can go with tan, white, blue (my preference), or really any other color. The key to making these look good is to wear them like you would wear the Vans or Chucks above. Throw them on and embrace the fact that they’re going to get dirty and used. If they start to see major gunking up, just run a suede brush over them a few times and you’re good to go again.



Loafers are the only thing on this list I won’t recommend to high-school kids. Even the saddle shoes below are affected enough that a young guy can wear them but loafers are too grown up. In fact, I’d venture to say these are for seniors and grad students only. However, if you do find yourself in that age group, loafers are awesome. They’re honestly as comfortable as a pair of slip-on Vans but you can wear them to a job fair and still look better than everyone else there. I’ve broken in my loafers so much that they’re my go-to-shoes when I’m doing things like making a run to the post office or the grocery store.

Saddle Shoes



These will be the dressiest on the list. In fact, to many of you, these wouldn’t be considered casual shoes at all. I have a pair like those pictured above except they’re white and a cream suede and I love the things. The thing about saddle shoes is that they are the epitome of High/Low. You have to have the right attitude to be able to wear these and that attitude is more difficult to attain the younger you are. I have yet to wear these without getting a couple of compliments from people I bump into. If you’re debating them, know that darker colors will stand out less and also look more casual. The lighter they are, the more you have to be able to wear them without any sense of self-consciousness. Those burgundy and grey guys above would be a perfect first pair of saddle shoes.

A quick note about the shoes listed: I am an affiliate for the companies I have referred to above. That means if you decide to click on the links and buy any of the shoes here, I get a cut of the price. Yes I would love it if you would do that. No that doesn’t mean that’s why I’ve recommended these products. I’ve chosen to work as an affiliate with companies whose products I am already familiar with and was recommending before I started getting a kick back. I own both the bucks and the saddle shoes above and am happy to recommend them because they’ve been such great shoes.


PS. Don’t forget I’m running a deal on Basic Consultations all month this month as a back-to-school special.