Compared with him, my collection is pretty tight – I’ve got just three watches in the rotation. An everyday watch (Rolex Explorer ref. 1016 from the ’80s), a crossover watch (a Tudor Prince from the 1960s with a handmade camel suede strap), and a dressy watch (an early ’70s gold Zenith, usually with a navy NATO strap.) So it’s kind of a spartan selection but covers a lot of ground. In the bullpen, I have a couple of old Heuer Chronos, an Omega, and a Zenith pocket watch. But between the first three, I can go almost everywhere.

I’m sure some guys pull their outfit together around their watch – especially the kinds of guys cruising HODINKEE – but for me, my watch is the last thing I put on before I walk out the door every morning. It’s definitely a part of the look though. In fact, we design our shirt cuffs with the buttons kicked back just a hair so that a wristwatch can fit more easily underneath. It’s a small thing – figuratively and literally; it’s like a quarter-inch, and it’s not gonna feel weird on the other wrist or anything – but it goes to show you that the watch is not an afterthought.

Ultimately, I think of a watch as the final lever to pull, style-wise. You can pull it to give a touch of formality to what you’re wearing, to chill your look out a little bit, or just to play into the color story. Here’s how I approach it.

First off, I looooooove a high-low mix. When I first started my business in 2007, it was really important to me to have a fairly broad spectrum of menswear. I wanted suits and shirts handmade in Italy as well as blue jeans and swim trunks … all in fairly close proximity. In the same way, I think a Timex looks super cool with a navy suit, and a Rolex Explorer can be great at the beach.

Word of warning here: Don’t take extreme contrast too far. For example, I might do my Zenith – my most formal wristwatch – with jeans and a poplin spread collar dress shirt, to give the rest of the look a bit of a lift. But that same watch with jeans and a polo would be one toke over the line … not quite right. The outfit’s just too casual for a watch like that. So I guess Rule No. 1 is that the rules are looser than you think, but there are rules. It gets easier the more you do it.

Rule No. 2: Whether it’s watches or clothing (or rock ’n’ roll), I’m big on the philosophy that your outfit should only have one lead singer. Maybe that’s a blazer with a strong glen plaid pattern, or a pair of colorful garment-dyed jeans, but not both. In the same way, a statement watch looks its best when everything else is fairly quiet … so the watch can sing lead. Consider maybe wearing a JLC Polaris Memovox with a graph-check shirt and a pair of blue jeans. That’d be good. But you don’t want a colorful strap AND a bright cashmere sweater AND a bold stripe shirt … unless you’re David Hockney, in which case, go on with your bad self. For most of us, though, too much is too much.

Rule No. 3: Your watch doesn’t need to match everything, but I like it when it hooks back to something. Just a small tie-in. Like today, I’m in a tan and brown tweed jacket, sky blue pencil-stripe shirt, and I’ve got a Prince of Wales wool tie with a bit of orange and navy in it. The Explorer would have been great … a layup. Instead, I grabbed the Tudor Prince because I liked the hookup of the cream dial and the suede strap with the kind of caramel-y, wheat-y color situation I’ve got going on.

Again, I made this decision 15 seconds before heading out this morning. It was a small thing, and I’m sure hardly anyone notices it, but it makes me feel good and a bit tighter.

I think that’s the deal with watches, in general. No one really needs them to tell time – we’ve all got our phones and our computers and the dashboards in our cars – but we love them. I wear mine more because it looks cool, which makes me feel cool, too. Which, hey, is exactly what clothes do! At least for me.

Sid Mashburn is a designer and the namesake proprietor of five menswear shops, located in Atlanta, Washington D.C., Dallas, Houston, Los Angeles, and online.