stylish guy in chuck tailors

These Three Pairs of Shoes Should Be The Foundation of Your Wardobe!

Let’s start with the bottom and work our way up. Since we are new at this and all, and by we, I mean me. Shoes are a very important element to any style.  It really does not matter what you do daily, your shoes are something you should give a bit more thought to. I promise I will not promote dressing up in fancy shoes everyday. However, shoes can make an outfit, and in some occasions add a bit of playfulness to your style.

I think every man is best served by a foundation when it comes to shoes. Three good pairs of shoes is really what every modern gentleman should have in his closet. Think of these as the base. The staple items if you will. There are many different styles of shoes for many different occasions and situations. For this essay, however, I am sticking to just three of the basics. Black semi-dress shoes, brown semi-dress shoes and sneakers/trainers.

Black Semi-dress Shoes

Sealed in the foundation of wardrobes across the world. Black semi-dress shoes are good for almost any suit or outfit. I say semi-dress because this does not have to be something that you only wear with a suit. They are the easiest shoe to pair with different outfits either casual or more formal. Because black shoes are so versatile, you will find that there are ALL KINDS of black shoes. The choices in styles can be really staggering. My recommendation is to stay away from the more casual looks, like say, Sketchers. Any black shoe that looks like it may be a sneaker should be overlooked for something more stylish. I mean c’mon. You are better than that! And stay far FAR away from patent leather. Unless you own your own tux or have super spy capabilities. Then stay the hell away from them. You really want to look for shoe with a little personality. Nice leather upper with a thin sole and hard heal. Something sharp to augment, not only your style, but to show that you take more into consideration than just your comfort.


As for pairing black shoes with colors and outfits—that’s easy because they go with just about everything. I personally never wear them with navy blue, but I have seem some guys pull it off. Specifically, I wear them with grey slacks, black belt and white button-down shirts. They also go fantastic with brown/beige chinos and a light blue polo. Casually I can be found wearing them with well fit jeans, a white v-neck tee, and fitted leather motorcycle jacket. It’s great for that casual night out with my girl.

Brown Semi-dress Shoe

You can go with wingtips, captoes or just plain oxfords but the brown semi-dress shoe is a versatile style element. Brown shoes look great with jeans as well as that three piece you have in your closet. They pair best with blue and gray slacks and can even look great in the summer with a pair of khaki chinos and a simple white button down shirt.

When looking for brown shoes it is about the shade of brown. You will find that there are many different shades ranging from very pale, almost sand colored, to dark chestnut. That is fine, the color choice depends on other elements in your wardrobe but I can tell you that medium to light brown shoes are the most versatile.  Go too dark and they get harder to pair with certain things.  Too light and they look bad with khakis and light colored chinos. I also recommend shoes with polished leather uppers, thin soles and hard heals.  Nubuck is too casual for my taste and not as compatible with my professional lifestyle. As for suede, well…that is a gamble.  Some suede brown shoes are very sharp, however wearing suede shoes requires you to consider weather and environment conditions before you choose to wear them; as they are hard to clean and should not get wet too often.

Stick to the all leather upper and lets start from there. You will not go wrong.  Trust me!

Casual trainers, sneaker, tennis shoe, whatever…

I have lived in a few places and this form of footwear is called many different things.  Here in Philadelphia we call them sneakers.  This is my blog, and I am in Philadelphia, so let’s just call them that for now.  Okay?

Now that is out of the way, this may be one of the toughest in terms of style. Most people do not think about sneakers as stylish, however we do care very much how they look. Sneakers can serve many purposes they can be used to train at the gym, or just to slip on to get to the coffee shop on Saturday morning. Since a sneaker can serve two functions, one for performance, and one for style, I think we should stick to one track. For this article I am going to focus on the function of style. If you want to be stylish at the gym, then I praise you, for now let’s stick to subjects outside of our workout.

A sneaker is effectively used for comfort but can be used for both style and activity. If you are the type to wear the same sneaker everyday; that is most likely going to be one beat up shoe. If you do wear them every day, I will venture to say that you probably do not clean them very often either. So, you are basically wearing a shoe that is comfortable and easy, but not going to impress anyone. This is totally fine, but would you wear that same sneaker to, let’s say a date?

If you said, “yes”, there is an upcoming post on dating I suggest you read.

If you said “no” then good on you but you should still read on.

Being comfortable does not mean you have to wear something beat-up. A nice pair of Puma’s, Adidas, or even Chucks can be purchased and used for those occasions where you want to be very casual but still look put together.  Sometimes a well chosen pair of trainers gives an outfit a bit of cheek.  Red sneakers seem to be the most popular for this, as well as light blue and also white. Depending on what you are wearing of course.
I have a pair of red suede Converse One-Stars that I love to pair with light gray slacks, white button down shirt, purple tie, green v-neck and a sport jacket. It looks super sharp but playful. Normally I am just slipping on my pair of Puma’s to run out to grab some take-out or when I am doing things around the house on the weekends.

Where Do You Find Them

Did you think I would leave you with just a rant about why you should own these three shoes.  How about we go shopping for some.  I have had friends ask me, where I get my shoes and this should be no different.  I make no money from adding these links and I have no affiliation with MyHabit or Amazon, but if you want a great deal on some fantastic shoes, here is the list of the examples above and where you can find them for an affordable price.

Black Semi-Dress shoes on MyHabit:

Brown Semi-dress shoes on MyHabit:

Sneakers/ Trainers on MyHabit and Zappos: