The Hipster Wore a Fedora

… And was oblivious to the fact that it looks ridiculous.

For the love of all things holy, ladies and gentlemen, if you wear a hat please ensure that it matches your outfit. A hat is made to complete an ensemble, not to be the centrepiece of it. If you are wearing a T-shirt, don’t put on a fancy hat such as a fedora. It doesn’t look stylish, it looks like you have no understanding of how to dress properly.

The magical thing about fedoras is that they work very well with suits. If you’re going to wear one, it should be with a suit (or at least a blazer/sports coat)- end of story.

So, here’s what you should wear with certain popular hats:

Baseball cap:

English: Blue Baseball Cap

The most casual hat there is. Looks good with a sports jersey, or a T-shirt and shorts. Not for use with “fancy” clothing.

Driver/Duckbill Hat:

New Cap!

Not necessarily the same thing, but similar enough. These hats are a little more stylish than baseball caps, and so do not belong with a T-shirt and jeans. Wear at least a polo shirt, or other collared shirts- Trousers instead of jeans make the outfit more complete; but a suit is always best.


Bucket hat

Dress in comfortable loose-fitting clothes. You’re clearly on vacation if you’re wearing those.

Cowboy Hat

Felt beige cowboy hat on a white background

Fun the wear, but rarely appropriate. Unless you work on a farm, or are attending the Calgary Stampede, this hat is not for you. Wear it to accompany long-sleeved flannel or denim shirts. Don’t forget the cowboy boots.


Line drawing of a fedora.

One of the more formal hats there is. The fedora was the big style in the 1940’s, at least if gangster movies are to be believed. You’ll notice that people in those movies never wore these hats without a nice suit.