How To Choose The Right Belt Size (Your Most Asked Men’s Belt Questions, Answered!)

If you’re unsure about things like how to choose your belt size, how long your belt should be, or which belt to wear with jeans… well, you’re not alone! Read on for the answers to some of your most asked men’s belt-related questions.

Men’s belts are a funny thing. We don’t think about them much until we need to… like when we don’t have one that matches, or when it doesn’t fit right.

I want you to have the right answers to your belt questions once and for all. It’s easy to overthink most things with men’s style, but I assure you this won’t be nearly as complicated as you might think.

Common men’s belt questions

First off, most of the belts you’ll see in this article are from Anson Belt. I’ve been wearing them exclusively since 2016. I just haven’t come across anything that looks as good and is as easy to use for the price.

The biggest problem with traditional belts are the holes. When you only have 5-6 options, you have to make sure you’re picking the exact right size. And gaining / losing weight? Don’t even think about it.

Plus, when using the same belt hole over and over again, for years, the leather looks old and worn.

Anson makes belts without holes. With Anson’s holeless belt system, you get 30 size options, spread ¼“ apart. The traditional belt? 5 holes, about 1” apart.

So this system, plus never having to worry about an old-looking, worn-out holey belt… those two things are reason enough to try out Anson Belts if you haven’t already.

By the way, I always suggest the box set. It’s a great deal! $99 gets you 6 different belt/buckle combinations. Learn more and buy a set here.

Thanks to Anson Belt for being a sponsor, and thanks to you, dear reader, for supporting the brands that support us.

“How do I choose the right belt size?”

When buying a traditional belt, you should choose a belt one size up from your pants size.

You don’t have to measure your belt, you don’t have to bring in old belts to the department store to compare sizes, just buy one size up.

I’m honestly not sure why the sizing system works this way. You’d think if you were a size 32” waist, you’d buy a 32” belt. I’ve made that mistake before, and the belt didn’t fit. I’m pretty sure I could only use the last hole at the very bottom of the belt.

So if you wear a size 32 in pants, buy a size 34 belt. If you wear a size 38 pant, buy a size 40 belt, and so on.

To be honest, I haven’t dealt with belt sizing and belt holes for years because of my Anson belts. I suggest just switching over to them now 😉

When you buy an Anson belt, you get one extra-long 56” leather strap you trim down to size. You could have a 50” waist and these belts will fit you just fine. And of course, they will fit whatever size you are.

So if you don’t want to worry about sizing at all, go with Anson.

“How many belts do I need?”

If you’re going for a truly minimalist closet, you really only need two belts. Heck, I could even say one belt, if you only wear one shoe color.

Here’s my definitive answer: You should have at least one medium brown belt, and one black belt.

If you had to choose only one belt, I’d go with a medium brown leather and matte white metal buckle. It can go well with most other shades of brown shoes, plus your sneakers.

The only thing a brown belt doesn’t go with is a pair of black shoes. So if you wear lots of black leather shoes or sneakers, you’d obviously need a black belt as well.

I should also mention that when it comes to matching your belt and shoes, getting close is good enough.

If your belt is a medium brown color but your shoes are slightly darker, no one’s really gonna notice, and no one expects you to have a perfectly matched belt for every pair of leather shoes you own. 

“Should a belt stick out?” “Is it OK to have my belt hanging down?”

You may be wondering how a belt should fit, or the proper belt length.

A bit of extra length is OK, but you don’t want it to be so long that your leather strap extends past your belt loop, or your canvas / woven belts are hanging down all flaccid and limp.

By the way, you may see this worn on the street—an extra long canvas belt that hangs down is a trend. But trends come and go, so if you’re going for a classic look, stick with a length that doesn’t hang down.

So what is the proper belt length?

Typically, the belt strap should end between your first and second belt loop. If you have enough extra material to loop it through the second belt loop, it’s too long.

If your belt doesn’t extend through the first belt loop, it’s too short.

So make sure you’re wearing a size that’s long enough to be worn properly, and ends somewhere in the middle, between the first and second belt loop.

“What’s a good casual men’s belt for jeans?”

While you may think all belts are the same, there are in fact dress belts and casual belts, and they’re very different!

Dress belts—the ones you wear with suiting trousers or dressier chinos—are generally slimmer (1.25”), and in a dark brown or black leather. They have an even finish with a slight sheen or polish, very minimal or invisible stitching, and a slim polished or matte buckle.

Casual belts, on the other hand, can be wider (1.5”+). They may feature distressed leather and / or metal on the buckle, and usually have visible stitching. Additionally, you’ll find casual belts in all colors. Casual leather belts can be natural and undyed, all the way to black leather.

So for jeans, you want to go with a good casual men’s belt with the above characteristics. Anson has a ton of casual belt options.

A dress belt with jeans wouldn’t make sense. There are a few exceptions, but in most cases, you’d be safe with a casual belt.

“What’s a good belt if you’re dressing up jeans?”

If you’re wearing jeans with a dress shirt, sportcoat, and dark brown brogues, for example, go with a casual belt that has minimal distressing. The more distressed the leather and buckle is, the more casual it is.

So you could have a casual belt in a dark brown, non-distressed leather, with a matte buckle. That belt would work well with this kind of “business casual” outfit.

“Should I wear a black or brown belt with jeans?”

This is an “it depends” answer. You’ll want to think about two things.

1.) “Am I wearing black or brown shoes?”

This is the easiest way to answer your question about which belt to wear with jeans. If you’re wearing brown shoes, wear a brown belt. If you’re wearing black shoes, a black belt.

And if I’m wearing sneakers, I wear a saddle tan leather belt with my jeans 95% of the time. I usually wear white leather sneakers or grey suede trainers (they look like luxe running shoes).

Saddle tan is my favorite leather color, but of course, a medium brown belt will be your safest, easiest, and most widely used leather color choice for jeans.

2.) “What color are my jeans?”

Let’s say you haven’t decided on shoes yet. I’d consider how dark my jeans are, and go with something low contrast.

So if you’re wearing dark wash jeans, go with a dark brown or black belt. If you’re wearing medium / light denim, you can wear a medium brown or saddle tan leather belt. And then choose the appropriate, matching shoes for those belts.

I suggest not wearing a dark brown or black leather belt with light jeans, or light saddle tan leather belts with dark jeans. It’s not “wrong”, and it can be done well, but if you’re going for a classic, easy-to-pull-off style, stick with low-contrast combinations.

Does this help?

I hope this article helped answer your most-asked men’s belt questions! Make sure to check out Anson Belt’s box set. I swear by their belts (I say this even when they’re not sponsoring the article, as many of my long-time readers know)

The box set is a great value. $99 and you’re getting 6 belt combos. If you break it down, that’s like $16.50 per belt, and you’re getting good quality leather that’s gonna last.

I’m still wearing my original straps and buckles from 2016, so I say this with confidence. Check out Anson Belts here →

And if you have any questions about belts in general, feel free to tweet me, or DM me on Instagram.