So this is actually in response to a question I got from a viewer that’s asking about what kind of shoes to wear with dress pants. He said that in his job, he wears dress trousers 90% of the time and isn’t sure that he’s always making the right shoe choice. He’s also not a tie or a sports jacket guy and that’s not required for his work. He also mentioned that most of his dress pants consist of light grey, dark grey, navy blue, light blue and tan. OK then, let’s get into it.
Consider the occasion
The first thing to consider is the occasion. Now, in this case, it’s work attire so we have to figure out what’s appropriate for work and if there’s a specific dress code. Is it a more casual setting, business casual, or something a little more formal? Maybe you’re going to a wedding, or a casual dinner party, or an awards banquet of some sort. Dress trousers can work in all of these settings, but the shoe choice will vary depending on the occasion.
So let’s chat briefly about the formality levels of different shoe types. We’re not gonna get into sneakers because obviously that’s a very casual shoe. Let’s start with slip on loafers as the most casual, and move up from there. Consider the loafer as the most casual shoe you can wear with dress trousers. I don’t own any Brown loafers which surprised me, so these blue ones from Paul Evans will have to do for the purpose of this video.
One level up from loafers would be something like a double monk strap or a single monk strap shoe. Even though these look really nice, it’s just a unconventional shoe design and that makes it further down on the formality scale. Still a very fantastic shoe choice, but it is going to be more casual then what’s coming up.
The next shoe would be a Wingtip Derby or an Oxford with a lot of broguing detail. The Derby will always be more casual than an Oxford, but for the sake of this video I put them both in the same category because of the brogue detail. The more medallion’s, wing tips and brogue detail the shoe has, the more casual it is. Now because both of these shoes have a lot of broguing work, I’d put them in the same category, although, the Oxford would be one step up from the Derby.
Moving on from there, we have a few cap-toe shoes. Now as you can tell, these are very clean and minimal shoe designs with not a lot of attention-grabbing elements like wing tips and medallions. You can easily go with black, dark brown, and burgundy (or oxblood). All of these would be acceptable for something that’s more on the formal side.
Moving on from there, we have the whole cut. As you can see, this is a very clean shoe with no detail whatsoever. The whole cut, or one cut shoe as you can see is made from one piece of leather with only one seem in the back. The leather is typically of a lot higher quality because there’s nowhere to hide any imperfections. The entire section of leather needs to be relatively flawless in order to make a shoe like this.
One step up from that would be a tuxedo shoe with a very high shine like patent leather. Now, that’s not something you’re gonna wear to the office, because that type of shoe is reserved primarily for black tie events. Now, I don’t have any tan dress trousers, but make sure you watch the video and let’s get into pairing these shoes with some different dress trousers that I do have and see what we can do.