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The Best Hat for Your Face Shape: 5 Easy Steps to Finding THE ONE


      "Hats just don't look good on me!"

      The HooDoo Haberdasher Debunks 

      This All-Too-Common Headwear Myth

      I hear it all too often when I tell someone I’m a haberdasher. This person recalls browsing a store’s collection of hats looking for something that speaks to them – for many it’s the first time they’ve ever even been in a hat shop. Maybe it’s a sophisticated fedora for him. Or perhaps it’s a ladies’ floppy brimmed hat. Time to try it on and see ….

      “Ugh, no. I took it right off. [Sigh] … hats just don’t look good on me.”

      Then, I explain how some hats actually don’t look good on some people, but there are as many hat styles as there are head and face shapes. A little guidance and some patience goes a long way, and that can’t be found at some novelty store that “just happens” to also sell hats. At the headquarters of HooDoo Headwear in Chicago – as specialists in the field – we’d say so when that floppy brimmed hat doesn’t complement her round face. Or when that Trilby just doesn’t suit the angular nature of his square-shaped face. We’d move on to our collections of alternate choices, maybe Newsboy caps or Fedora Style hats, and explain that there is a cool hat out there for everyone!!

      Because in addition to the materials, color and personality of a hat, you need to know that certain styles of headwear are more flattering to your build or facial shape – and we promise to point you in the right direction.

      The problem is that most online advice is a ridiculous process involving a measuring tape, calipers, a lock of hair, your first born child and other nonsense. Yes, these tools can help, but there is an easier way to get a general idea of your face shape without taking a 3D laser scan of your noggin.

      5 Easy Steps to Finding a Great Hat for your Face Shape

      1.Pull hair back.

      2.Grab a bar of soap.

      3.Stand 2-3 feet away from a mirror.

      4.Trace your face.

      5.Step back and admire your artwork.

      What do you see?


      Round: Your face is symmetrical in width and length, with full, happy cheeks. Lucky you: A round face shape makes you look younger.

      HooDoo You Love: Johnny Depp

      Hat Picks: Soft Shape Fur Fedoras


      Square:Like the round face shape, you’ve also got great symmetry with your face length and width. But you’ll see a bit more angularity from cheek to cheek. You’ve got so many options to flatter your face.

      HooDoo You Love: Kate Middleton

      Hat Picks: Fascinators, PillBox Hats, Dress Chapeaus, Custom Millinery


      Heart Shaped: Your chin is the narrowest part of the face, and your forehead and/or cheekbones may be a little wider. Great news for you, because heart shaped faces draw attention to the eyes.

      HooDoo You Love: Leonardo DiCaprio

      Hat Picks: Stingy Brims, Newsboy Caps, Trilbys


      Oblong: Longer than it is wide, your oblong face highlights similarly sized features – like your forehead, jawline and cheeks. You might also have a higher forehead, prime real estate for an awesome hat.

      HooDoo You Love: Sarah Jessica Parker

      Hat Picks: Cloches, Asymmetrical Toppers, Ladies Fedoras, Mens Newsboy Caps

      But – in spite of all these useful tips – keep in mind that these are guidelines, not rules. Fashion changes all the time, and the best hat is the one that you FEEL the best in. It’s always a good idea to match your headwear to your personality or mood – even the event to which the hat will be worn should be part of the consideration.

      Pigeonholing into the same ole headwear is the last thing we want. Break the rules, be distinctive; the hat itself will actually “tell” you when it is right (or wrong). Remember, a good hat can make a powerful statement and that statement varies with every customer. HooDoo guarantees compliments, so don’t worry: We won’t let you buy a hat that is not flattering to you. We hate to say it, but you are a walking advertisement for our shop! If your hat doesn't look and feel great, we’re advertising ourselves out of business.

      The real takeaway is that your mind is like a parachute: If it’s not “open” you’re gonna crash and burn. HooDoo Headwear wants you to look exceptional, so take a couple of minutes, select a few options and narrow it down to the hat that “speaks” to you. Remember, you wear the hat, the hat doesn’t wear you.

      Now, check the website for some ideas, stop by the store or call if you can. And remember to go clean the mirror!!

      Check out our online gallery of top quality hats for distinguished  ladies and gentlemen. Or visit us at our flagship store, just minutes from Downtown Chicago at 111 N. Marion St. in Oak Park.