Grown Man Shxt: Walk It Out (Part 1)

“Good Shoes Take You Good Places.”

Okay guys we are finally here. This is the first installment in my series concerning fashion. We’ll be working from the bottom up to get your wardrobe out of 2008 and into the modern era. I could’ve started with pants, tops, accessories, headwear, or even cologne, but that’s not what detail-oriented people notice most about a guy. The thing that is going to really separate the guy from the pack is the shoes on his feet. Shoes are the understated foundation of any good fashion ensemble.

You should NOT be looking like a Dipset extra in 2022

Rule #1 of fashion: Everything ain’t for everybody. The biggest mistake most people make is seeing what some celebrity, athlete, or entertainer is wearing and looking to replicate that look. Fun Fact: Most of the people you see on a red carpet have a stylist. They have a fashion expert whose paid role is to pick clothes for that person based on their requested criteria. Beyond this, you may not have the same body type, same demeanor, same social circle, or be the same fashion stalwart that many of those people are. Just because you see someone famous doing it does it mean it will work for you. This doesn’t necessarily just apply to celebrities either. Just because you saw your homeboy rocking a certain look and he was getting the eye of a bunch of the womenfolk doesn’t mean you can clone it and it will work. Fashion is about SELF expression not necessarily what’s trending within a certain group.

You aren’t everyone else. Fashion should be and expression of yourself

We are going to start more formal and get casual for part 1 and get more casual from there. There isn’t a need to start with sneakers. Most of us have been wearing and desiring sneakers since we were little kids. There are all sorts of commercials and endorsements from pro athletes for sneakers. Hype beasts and the manufacturers have fully invested in sneaker culture in the form of limited edition colorways and hip hop artists having their own brands. More formal shoes are less talked about and, to be honest, don’t get worn as much by most men. That fact is another reason that properly integrating more formal shoes into your more casual wardrobe will help you stand out and is another way to express yourself.

Shoes follow the same rule that applies to most of fashion, you get what you pay for. Shoes run the gamut. There are $30 oxfords and $2500 loafers. What works best for you is about your wallet and the look you want. I personally don’t skimp when it comes to shoes and that area more than almost any other part of the wardrobe is the place that I’m the least willing to cheap out. This is because I look at shoes as an investment. I wear a size 14 so it’s not like my size exactly grows on trees. Here’s the other interesting fact that makes shoes a worth investment. Higher-end dress shoes have a much longer shelf life because of the materials used. Now that may seem like common sense but it’s a little bit deeper than that. Most high-end dress shoes have leather soles as opposed to plastic or rubber soles. With plastic or rubber soles when the shoe wears out, it’s basically dead. You’re going to need to buy a new pair. With leather soles when they start to wear out you can take them to a cobbler for a resole that will basically make the shoes like new. You can buy the same cheaper dress shoes for $70-$100 dollars every time or you can keep those comfortable leather-soled shoes for 15+ years and keep them looking like new!

High Quality Dress shoes allow for a Cobbler to make them look brand new relatively inexpensively.

Shoes are a bit weird in that it’s definitely one of those “if you know, you know” type of situations. High end shoe guys will know immediately if you have on a pair of Berluti’s vs a pair of Stacy’s. That doesn’t mean that you can’t shop within your price range and go for the types of shoes that work for you. But before we get into ways to pair shoes let’s talk about the main categories of dress shoes.

Oxfords

These are the most common dress shoe on the market and the most common ones you’ll see people wearing with business suits. They are tried and true and always a safe bet when comes to non-denim attire (slacks suits etc).

Loafers

Loafers are your go-to no laces dress shoe. They can be a bit riskier for someone with a conservative fashion sense, but you don’t have to be daring for them to work. It’s important they fit well as they have no lacing.

Derbys

At first glance, Derbys appear to be a variation of Oxfords. But upon closer look, they are a different shoe. The primary difference is in the open flaps around the lacing for Derbys as opposed to the closed lacing for Oxfords. Derbys are considered less formal than Oxfords which plays positively in its own way. I believe universally (not necessarily for my personal style) Derbys are the most versatile dress shoe for me. As a dress shoe, you can pair them with a more casual look but they still fit many suit styles as well.

Monk Strap

Monk Strap shoes have been rising in popularity in the last ten years and most shoemakers make some variation of them now. Monk straps are my personal favorite and the most versatile shoe in my arsenal as they pair well with almost everything I have in my closet.

Note: This is not a full detailing of the different types of dress shoes as there are many more than this (like enough to write a book about). Many formal shoes have multiple subtypes and variations as well such as broguing. Boots including dress boots aren’t covered here as they will have their place in another entry.

So we’ve got a basic understanding of the 4 major dress shoe types. How do we integrate them?

My personal style is a bit more formal and understated so I actually wear more formal shoes (loafers and derbys) with my casual fits. When wearing jeans and a T-shirt I’ll usually pair them with some derbys in the fall/winter and loafers (no show socks) in the Spring/Summer.

Adding Dress shoes to a casual fit can make it more refined.

It seems basic but it’s a game-changer for your wardrobe. I believe there aren’t any don’ts in fashion but there are 2 major “you probably shouldn’t try that” things when it comes to pairing dress shoes.

1. Shorts

Shorts and oxfords don’t mix. Loafers and Shorts don’t mix. We’re talking about formal shoes and formal loafers don’t belong with shorts, as shorts are the ultimate Casual clothing. Derbys? Maybe. Derbys are a bit more casual. They can make an ensemble a bit more snazzy. Monk Strap? If you’re daring they can be pulled off, but you’re likely already a fashion risk-taker.

I want to be clear. If you're wearing “around the house” shorts (running shorts, cargo shorts, hoop shorts, etc.) you do not have any business wearing formal shoes.

2. Sweatshirts/Hoodies

If you’re wearing a sweatshirt or a hoodie then that is way too casual for formal shoes. The exception to the rule might be derbys, they are just casual enough to pull off for sweatshirts, especially those designer types. Hoodies and formal don’t mix. Wear a cardigan, a bomber, hell even a down jacket, but not a hoodie.

We’ve covered formal shoes. There are a bunch of different sub-types for formal shoes and many different ways to wear them that can change the look of your whole fit. It’s something I’ve had to discover for myself over time what works for me based on the look I was going for and what i’m into. I wear formal shoes way more often than I wear sneakers these days, but It’s all about you and your self-expression!

I want your feedback, let me know your thoughts! Leave a comment or hit me up on IG and FB.

- Rob Immortal