Thanks for the questions, David. Totally understand how easily belts stack up through the years… and it's not always super clear when to wear them with what, and when to clean 'em out. But I think we've got a solution for you – fewer belts that go with more things.
My ace belt – the one I wear the most, and the one I can wear easily from suits to shorts (and everything in between) – is a one-inch chocolate brown belt, in either pull-up or bridle leather. Both have a one-piece strap that took us a year and a half to get right. They both come with super-simple brass buckles – unlacquered; we dig a patina – that you can easily swap out. So you can really just get one belt and go wild with the buckle based on the occasion, the formality, or your mood. For instance, you could go with the original or a plaque buckle for coat & tie, maybe something a little more playful like an arrowhead or oyster shell for jeans and sport shirts, and something casual for shorts and a polo – a fishhook, perhaps. You could also just get it as-is and literally wear it with any pair of pants or shorts that happen to have loops. My main "other buckle" is the plaque buckle in brass. The silver version is great, too, just pricier - makes a great graduation gift. Or 25th-anniversary gift!
The best thing about both those leathers is they age beautifully – I compare them to a piece of vintage furniture – as long as you take care of them and don't forget to hit them with a little conditioner (the OG, Saphir Renovateur) from time to time. The pull-up starts out fairly pliable, while you've got to wear the bridle a little harder before it softens up, but both leathers will get better and even softer with age. And a quick note about the width on those. I like one inch. I'm six feet tall, and I like the proportion – it doesn't call too much attention to itself. And I think it works well for everyone. But if you're super tall, or a bigger guy, you may like the extra quarter inch on the 1.25" strap. Too much more than that, and you start getting into Gunsmoke territory.
So I'd start there, with the basic leather strap, and add at least one other belt into the mix that's got a little personality to it. This can almost act like a tie…your one decorative piece. This can be as simple as alligator or sharkskin, but I'd also consider something a little more colorful and casual (good for those sneaker days), like a polo belt, a braided belt, a beaded one from Kenya, or a D-ring ribbon belt. Any of those are a great wingman to a pair of chinos or jeans and are an inexpensive way to lift your outfit. My go-to for this is the zebra belt, which may be too wild for some guys, but I love it and probably bring it out once or twice a week. Ann and I both wear it so often that we have to kinda try not to match.
And speaking of matching. Does it need to match your shoes or your shirt? Your shoes, always. But it doesn't mean you need to put your shoes and belts in a lightbox to match them. Think about it – your shoes and belt are roughly 3 feet apart anyway. Sure, you want them to complement each other, but don't be too precious about it. Brownish to brownish works just fine. And if you're wearing, say…a pair of white sneakers, you don't want to go with a white belt. But what else in your outfit can complement that? Maybe a white shirt. Or a navy tie with white dots. Can the ensemble sing in harmony? It doesn't need to be too connected, but you still want to build some continuity.
While you can always go beltless, my rule is if my pants have loops, I'm wearing a belt. And for the record, you don't need 20 of them (so don't be afraid to toss the ones you don't wear,) but a few of the right belts can quietly kick up your outfit. An ace belt – maybe with an extra buckle – and a "personality" belt. Start there. That's a solid foundation that you can build on for a thoughtful collection. And spring cleaning always gives you a little bounce in your step, anyway. A great weekend project. Tighten up!