Top It Off: A Guide to the Best Hat for Your Face Shape

From heart-shaped to squared jaws, we’ll match the right hat to your features

Styling your hat isn’t just about color or logo, it’s also about how it enhances your face shape. Whether you have a round, square, heart, oval, or diamond-shaped face, certain hats can make your features pop.

Luckily, our Pro Shops are stocked with a wide range of performance and lifestyle hats from Imperial, the official hat sponsor of CityPickle, who have been crafting premium headwear since 1916.

Let’s break down the best CityPickle hats for your face shape, including one for the kiddos too!

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Performance Dad Hat Blue with Vintage Logo

Director of Retail, Alexis Karetzky

Best for: Oval Faces
Low-profile and lightweight, this performance hat is a natural match for the symmetry of oval face shapes. The soft structure and curved visor complement your balanced features without overpowering them.

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Dad Hat Green with Pink Horizontal Logo

Coach Extraordinaire, Kaitlin McCabe

Best for: Heart-Shaped Faces
We HEART this classic dad hat! It’s made with soft cotton and has a low slope, which balances out a broader forehead and narrower chin. It’s laid-back, flattering, and super breathable for summer days.

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White Hat with Green Vintage Logo

Head Facilitator, Victor Hernandez

Best for: Round Faces
A medium-structured crown and balanced depth give this hat a bit of height, perfect for adding some angles to rounder face shapes. Plus, the breathable fabric keeps you cool on and off the court. It also happens to be the favorite style of the world’s No.1 player, Federico Staksrud.

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Green Trucker Hat with Triple Logo (Pro Shop only)

Assistant Manager, Avery Hootstein

Best for: Square Faces
Structured and sleek, this mid-crown trucker hat softens strong jawlines and complements the bold features of square face shapes. Wear it when you're ready to make a statement.

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Performance Dad Hat Gold with Smiley Face

Assistant Manager, Brandon Roldan

Best for: Diamond-Shaped Faces
Don’t let your hat turn you into a diamond in the rough! The gentle slope and curved visor balance out the angles of a diamond-shaped face. This hat is both sporty and expressive, a perfect match for your standout look.

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Grey Beanie with Blue Horizontal Logo

Best for: Oval Faces
No visor, no problem. This cozy cuffed beanie pairs perfectly with oval faces and adds just the right amount of edge to your style, especially when temperatures drop.

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Kid's Performance Hat White with Smiley Face

Best for: Small Faces
Okay, this one isn’t about geometry, it’s just for our littlest players with smaller faces. This junior fit performance hat wicks sweat, dries fast, and spreads nothing but good vibes!

Upgrade Your Hat Game

Next time you swing by a CityPickle Pro Shop, don’t just grab the first hat you see – our helpful staff and coaches can help you find the one that fits your face and your style. Already know what you're looking for?

Browse all our styles online at shop.city-pickle.com.

Look good. Feel great. Play smart.