Bonus: Bullseye's 'Put You On' with Derek Guy

**SPEAKER_1** (0:00)
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**Jesse Thorn** (0:15)
Hey gang, it's Jesse. I just wanted to share something that is a little bit cool this weekend. It's a taste of our new Bullseye bonus show, which is called Put You On. What is Put You On? It is a show that is like Bullseye in that it is about what's good, but on Put You On, we are here to help you. We take questions from our audience members on just about anything, books, movies, cooking, and then a guest and I share our recommendations. Now, the show is usually only available for direct supporters of Bullseye. If you aren't already a supporter, you can support the show by going to maximumfund.org/joinbullseye.
This month, our guest is Derek Guy, my very longtime friend and collaborator on my Menswear website, Put This On. He's also the famous Menswear Guy from social media. He joined me for a special all-Menswear edition of Put You On. Here's a little bit of our conversation.
What is our first question, Kevin? Because I'm grateful to have, whenever I have a Menswear question that I can't answer, I always end up asking Derek. So, I'm glad to have some backstop here.

**Kevin** (1:28)
We have a cornucopia of Menswear questions too. Let's start with Southrow3506 who writes, any general tips for matching a watch band to an outfit? I just started wearing a watch and I've already been through several bands because I feel like none of them ever look good with my outfit.
Any tips or should I just stop overthinking it?

**Derek Guy** (1:51)
Yeah, I think when it comes to matching watch with outfit, I will say I also think that watches are very personal objects. And to me, especially if you wear long sleeves or jackets, they mostly remain hidden under a cuff. So I personally don't think you have to get too hung up on rules or whatever. But I do think that if you're wearing a suit, there is something very nice about a time only dress watch and a leather strap. And then if you're wearing a casual outfit, it's nice to have a sports watch. So to me, it's more about the design of the watch working with the outfit, assuming that you want to make it coherent.
And then to me, the watch strap is designed around the watch. I don't think you have to match watch strap color to your belt and your shoes unless you happen to have a ton of watches. And that day you want to wear whatever, like a black strap with your black shoes. I think that's fine, but watches can be kind of expensive. So unless you have a ton of money, I sort of think it's fine to have the watch strap work with the watch dial and the general design, and then the watch dial and design generally work with your outfit. So you have a dress watch and you have a casual watch.

**Jesse Thorn** (3:07)
Yeah, I think that like, rather than obsessing over the band, I would say there is a sort of band of levels of formality where it is appropriate to wear a digital watch with a rubber band.
And that is like very casual. Like I have these, I have a khaki colored G-Shock digital watch that I will wear when I'm putzing around in shorts. You know what I mean? Right. And then I also have this, I have this gold watch that belonged to my grandfather that's on a, that's on a black band. And I will wear that generally when I am genuinely formally dressed, whether it's, you know, a suit or black tie. I mean, traditionally with black tie, you don't wear a watch, I guess, but like if it's, if it's a serious business situation, I'll wear that like gold dress watch, black band, like serious watch. In between, I mean, think about how many like dudes are out there wearing suits with like a Rolex diving watch and nobody's ever like, oh, that's a sports watch. You were supposed to be swimming in that.

**Derek Guy** (4:20)
Yeah.

**Jesse Thorn** (4:21)
So I think in general, like free yourself of the tyranny. And you know, like the standard things apply, like a metal bracelet, I think, aesthetically is a little more flexible, but is traditionally a little more casual than a leather band.
Black is usually a little more formal than brown. I don't think your matching needs to be perfect.