Today’s question comes from Andrew. He asks:

“You never mention belts? Shoes and belts, should they match?”

There are two old school rules when it comes to belts and matching:

  1. Your leather belt color should match the leather of your shoes.
  2. The metal of your belt buckle should match the metal of your watch.

Rule No. 1 only applies to dressy shoes, like oxfords, loafers, and boots. Don’t try to match your sneakers, it’ll look stupid. (My go-to sneakers are white Adidas Stan Smiths. Can you imagine wearing a white belt?)

When it comes to why you should match your belt and dress shoes, it’s simple. When you don’t, it clashes and looks strange.

As for Rule No. 2, you can ignore it altogether.

It’s outdated. No one is going to notice or deduct style points from you just because your gold buckle doesn’t match your silver watch band. 

Now, some new school thoughts on belts.

NEW SCHOOL RULE #1: WHEN IT COMES TO A TAILORED SUIT, GO BELTLESS

beltless-suits800px
PHOTO VIA NICOLASRICCI AND SEEALAN

A trend I’ve noticed lately are men in suits going beltless. It might have to do with the fact that belts don’t make any sense. 

Consider: Belts are designed to help hold up your pants. Except if you follow the number one rule of style, make sure your clothes fit, you shouldn’t need a belt!

(Fun fact: Braces, or suspenders, do a better job of holding up your pants.)

Belts are also a big pain in the ass when you REALLY need to use the restroom. 

Going beltless in a tailored suit achieves a few things. It shows off the tailoring and fit of your suit. It also looks clean and elegant, and helps you avoid looking like a generic guy at the office with a Kenneth Cole belt. You know, this guy:

black-suit-bad

Jokes aside, I’ve been going beltless with my tailored suits lately. If you often wear proper tailored suits, I recommend trying out this look. It won’t cost you anything extra, and is a good exercise on “less is more”.

NEW SCHOOL RULE #2: ALWAYS WEAR A BELT WITH CASUAL LOOKS

belted-casual-looks1000px
PHOTOS VIA MARK CHO, PRESTON KONRAD, AND STEVEN ONOJA

When it comes to casual looks, I always prefer wearing a belt.

While I think belts are useless for holding up your pants, the best reason to wear a belt is to emphasize pieces in your outfit, thanks to an amazing psychological trick.

In a suit, where the jacket and pants match, a belt interrupts “the flow” of the suit. The bold line that’s the belt makes our eyes pause.

When it comes to casual outfits made up of separates, we can use that pause to our advantage.

Try this out. 

Scroll back up to the beltless men in suits. Notice how your eye looks at their suits up and down without interruption. This uninterrupted flow feels a lot more elegant. Think of it like a sushi master slicing fish with a sharp knife in one motion. That’s the feeling you want when you’re wearing a suit. Elegance.

Now look at the belted men in casual outfits. There’s so much visually going on, the belts tells our eyes to stop and look at all the interesting elements.

(In case you’re wondering: The term “separates” just means your clothes aren’t part of a matching set outfit like a suit is. An example of a separates outfit would be a Linen blazer and denim.)

Now that you have two new rules to consider, let me show you how to properly stock your wardrobe with the right belts, and give you some pointers on getting the perfect size.

THE 4 ESSENTIAL BELTS YOU SHOULD OWN

The four essential belts you should own are:

  • 1 Black casual belt
  • 1 Brown casual belt
  • 1 Black dress belt
  • 1 Brown dress belts

You can get away with less. If you only own black dress shoes, you don’t need a brown dress belt. 

But to be safe, I recommend stocking these four belts in your wardrobe. 

What’s the difference between a casual belt and a dress belt? 

casbelt-vs-dressbelt
CLICK IMAGE TO ENLARGE

How wide should I buy my belt?

The width of the belt depends on your pants. You want it to fit in your belt loops without bulging out. For casual belts, it’s a matter of preference on how wide you want it to be. 

If you’re wearing dress pants as a separate (without the matching jacket), always wear a thinner dress belt. A wider casual belt will look out-of-place and can also ruin the belt loops. 

How do I figure out what length to get?

belt-length
PHOTO VIA Business Insider

When it comes to the length:

  • Buy 2 sizes higher than your waist size. If you’re a size 34 pant, get a size 36 belt.
  • The belt should buckle on hole #3. This leaves 2 holes over, and just the perfect length tab to tuck into a loop. 

BRAIDED BELTS, FABRIC BELTS, AND ALL THE FANCY STUFF

BELTS VIA MR.PORTER
BELTS VIA MR.PORTER

Non-classic belt styles like braided belts, fabric/ribbon belts, and colored, I treat it the same way I treat colored and patterned socks. It’s a pop of color/interest, and should be used sparingly.

I recommend is using The Swap Trick to help you figure out the best way to incorporate these more interesting belts into your wardrobe. 

Going for a colored belt, like the blue suede one above, cancels out Rule No. 1. (Your belt and shoes should match) In this specific case, I recommend you do not match your colored belt with your shoes. It’s overkill.

Got a style question? 

Leave a comment and let me know! 

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peter@theessentialman.com'
Author

Hi, I'm Peter. I spent 11 years as a menswear designer here in NYC. Now, I help some of the most successful men look really good as a Private Personal Stylist and writer of The Essential Man. You can learn more about what I do by clicking here