How to Not Look Weird in a Hat: A Guide for Guys

How to Not Look Weird in a Hat: A Guide for Guys

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Hats are amazing. Worn right, they can make you emit confidence, make you stand out in a crowd, and hide your bad hair day. Hats are also a versatile accessory– from skate clothing to formal wear, hats and caps can be incorporated into any men’s fashion for any occasion. They’re even useful. As fall and winter approach, hats can help your body retain precious heat so that you can hustle in spite of the cold.

But pulling a hat off is tricky and can leave the wrong guy looking like a fool. Here are a few basic tips for the optimum cranial style.


  • Know Your Face ShapeA hat, like any other part of your outfit, is supposed to complement your body and highlight your best features. Figuring out whether you have a square or round face, or a long or short face can prevent you from picking something that makes your already-chubby face look like a bowling ball. In general, choose a hat shape that contradicts your head shape. Is your face long? Don’t get a high-sitting beanie. Got an angular face? Pick something with softer curves.


  • Know how it’s Supposed to FitWhile many fashion experts recommend sticking to a simple hat in a common style (baseball hats, beanies, or Panama hats) what style you choose to wear is up to you. However, no matter what style hat suits you, wearing a hat that doesn’t fit properly looks sloppy and, well, stupid. Take some measurements to determine your hat size, and do a little research, so you don’t pick a cap that squeezes your temples or flies off in the wind.


  • Wear the Right OutfitWhile hats can be casual, a hat perched atop a dirty or overly mismatched outfit will make you look ridiculous. Find the right balance between a hat that matches and a hat that matches too well– in general, your cap should stand out, but not so much that it looks out of place. Choose textures, patterns, and colors that stand apart from your outfit, but a style that matches the formality. For example, plain, white supreme baseball caps would make sense with casual, colorful graphic tees and skate clothing.


  • Practice Confidence
    A little boldness goes a long way, and can even impact your life outcomes. After all, people decide if they think you’re trustworthy in a tenth of a second. If you act nervous in your new look or constantly ask others what they think, chances are you’ll make the hat seem more unnatural than it really is. To get more comfortable, try wearing the hat around your house or for shorter periods of time so that your fidgeting doesn’t wreck your style when you finally brave the public.


Whether you’re into suits, athletic wear, or skate clothing, a hat can pull together any look, and make you stand out in a crowd. By following this guide, you can take your hat style from foolish to fine.

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