How to Look Good While Wearing a Hat

In this edition of Help Me Dress Myself, a stylist explains why not all hats are created equal.


Are you one of those guys who wants to look stylish but finds it doesn’t come all that naturally? We feel you. Don’t fret: With some advice from LA-based stylist Rayne Parvis, we’re all going to learn how to dress a little better. In this edition, we’re looking at which hat styles are acceptable and which look downright wacky. Also, find out how to pair a hat with the rest of your outfit.

Step #1: Keep it Simple

Many of us feel a bit silly in a hat, and the combination of self-consciousness and unfamiliarity causes a lot of guys to end up with something that just doesn’t work. Case in point: The unfortunate rise of the trilby hat (which most wearers mistakenly believe is a fedora: It is not). However, If you actually want to look good (and not ridiculous) while wearing a hat, Parvis suggest sticking to these five basic styles:

It’s also important to keep seasons in mind when choosing a hat to avoid looking completely out of place, Rayne explains: “Only wear Panama hats during the spring and summer season, and only wear wool hats—fedoras and heavy-knitted beanies—during autumn and winter.”

Step #2: Know Your Face Shape

Because the hat you wear will accentuate the shape of your face—i.e., a round hat will make your already round face look even more round, or a tall hat will make your already long face look even longer—it’s important that you choose a hat that’s the opposite shape as your face. “If you have a square face, fedoras, buckets hats and beanies are all good options,” Parvis explains. “If you have a round face, I recommend sticking with baseball caps or trucker hats.”

Step #3: Don’t Match Your Hat With Your Outfit

Too often guys look like they just threw on some random hat because they’re having a bad hair day. To avoid this, Parvis suggests choosing a hat that’s a different color and texture from the rest of your outfit—that way, it looks like you purposefully chose to wear said hat to spice up said outfit. Parvis adds that mixing styles may also have the same effect. “Semi-formal flat caps are the most diverse hat, in my opinion,” she says. “You can even dress up a T-shirt and jeans with a flat cap.”

In simple terms, the key to looking good while wearing a hat is choosing one that’s noticeable—but not noticeably silly.

If you have any questions about getting the look you want—fits, cuts, colors or anything else fashion-related—leave it in the comments and we’ll have a stylist answer it in an upcoming post.