Some of us just aren’t “hat people,” but for those of us that like to don some headwear, there are so many choices to make. Are beanies in? How do I pull off a bucket hat?  What the hell is a docker hat?

There is an entire world of hats beyond the simple snapbacks, fitted caps and dad hats. We’re going to break down a few types of hats, how to wear them and what to avoid.

Snapbacks vs Dad Hats

Adjustable caps are the safest bet with headwear. Unless you’re rocking some dreads or got a big head, you probably own an adjustable hat or two. The biggest difference between dad hats and snapbacks is the brims and adjustable back. Snapbacks mostly have a flat brim, as opposed to the curve brim of a dad hat. Additionally, dad hats come with a strap in the back, typically with a buckle. 

Do’s: Keep your dad hats simple and your snapbacks graphic-heavy. Stick to snapbacks if you have a bigger head.

Don’ts: Don’t match your sneakers to your hat when it comes to color. Unless it’s   small accents that match, we advise against matching your red Retros to your red Bulls snapback.

Bucket Hats

Not to be confused with the farmer-style hat your dad wears to weed the backyard, bucket hats are crossroad where functionality meets trend. Unlike the last category, these hats are a little trickier to pull off because they require that you find the right size and pattern (if any). 

The bottom line is, bucket hats aren’t as popular or common as other hats which make them the perfect piece to upgrade your style to something more fashion-forward if that’s what you’re going for. 

Do’s: Go into a shop wearing a fit you’d pair with a 

bucket hat to see how it would look all together before taking the dive. 

Don’ts: Don’t top a dressy outfit off with a bucket hat, because they’re best paired with athleisure and streetwear fits. Also, avoid heavy patterns unless that’s your vibe and you can pull it off. 

Docker Hats

You might have thought, “there is nothing more fashion-forward than a bucket hat.” Well step aside all headwear, the docker hats are in. A docker hat is a brimless canvas cap with folded edges. The newer styles also have a strap in the front similar to a regular strapback/dad hat. 

Dockers used to be exclusively worn by bearded warehouse workers who smoke out on the pier during breaks, but have since secured a spot in the streetwear game. They are typically used in minimalist fits with next to no graphics or patterns. 

Do’s: Slip a docker hat into your fall/winter rotation. They are a much better option for your overcoat fits compared to any other hats unless maybe a beanie which we’ll get into.

Don’ts: Opt out of any docker hats with patterns or heavy branding as it destroys the purpose of the aesthetic. Don’t pair one with only a t-shirt or tank, because these are meant to be styled with coats and/or button-ups.


What hasn’t been said about beanies? Despite their long history, beanies are still a hit or miss for most people. There are all these guides online with conflicting advice, so we’re going to try to keep it simple. 

Do’s: Stick to muted colors that won’t distract from the rest of your outfit. Get a beanie with ribs which will help fit your face’s shape instead of contrast it. If applicable, style your hair so that it’s showing and complementing your overall look versus using a beanie to cover it all up on a lazy hair day.

Don’ts: Do not wear beanies in summer. Never go for a pom beanie. Keep your favorite teams on your snapbacks, not your beanies. Avoid the oversized hipster beanies.