The Best Hats

Buying Guide

Is there any item of clothing as hard to pin down as a hat? Socks may come in wacky colors or designs, but they really only have one job, and you can only wear them one way. The word “hat,” on the other hand, contains multitudes. You might have a favorite hat that you never wash and depend on for nothing more than sunburn protection. On the other side of the spectrum are the elaborate pieces of architecture that you might see decorating moneyed ladies at the Kentucky Derby.

We could spend days talking about the storied military history of the beret or the evolution of the cowboy’s signature 10-gallon hat, but let’s assume you’re buying something on the more functional end of the spectrum. When it comes to utility, the questions on your hat-buying checklist will mostly be easy. Are you wearing it for shade? Buy a beach hat with a wide brim. Need something warm that will travel well? Try a stocking cap.

Fashion-wise, you should strive to fit the hat to your outfit. Practically speaking, the hat needs to suit your environment. Beach hats that have a woven straw look are very much in demand, but you may want to make sure they’re made of actual straw (or raffia, which is a more common fiber that’s just as durable). Cheaper beach hats will more likely be made of braided and treated paper that won’t hold up as well to the elements.

On cold days, go for a hat knitted with wool or cotton. Cotton has the advantage of being naturally hypoallergenic, while wool is more breathable and better at wicking moisture away from your brow. In the summer, polyester caps are affordable and can stay dry even in heavy sweat. Mesh baseball caps are always a good bet, though they won’t provide much protection from the sun’s rays.

Browsing different styles is half the fun of buying a hat online but you’ll soon need to answer the most important question: Will it fit?

If all you wear are baseball caps and other hats with an adjustable band, you might go your entire life without needing to know your hat size. If you’re ready to level up to something a bit more fashionable, though, it’s easy to find out your hat size. Wrap a tape measure around your head at the widest part of the temple and take down the width in inches; Stick a finger under the tape as you measure to allow for some wiggle room.

Men’s sizes vary slightly from women’s and you should be able to find an exact conversion chart online, but in general: “Small” hats will fit a head up to 7 inches. “Medium” sizes cover 7 to 7 1/4 inches. “Large” hats are for those with measurements from 7 1/4 to 7 1/2 inches and “X-large” are for 7 1/2 to 7 3/4 inches.