How to Find a Flattering Hat

It’s time to admit it. Fall is on its way out. Winter is coming, and we need to break out the hats. People tell me all the time, “Hats don’t look good on me.” A couple years ago, I styled a photo shoot with a real woman (as opposed to a model) for the cover of a magazine. She gave me the same line. After sizing her up (very high forehead, wavy hair, petite frame), I borrowed five hats from a department store that looked great on her. She was thrilled and bought all of them. Not every hat will look good on you, but I promise you that there is a hat for every head. Keep reading for my tips on how to find a flattering hat. Let’s start with a hat dictionary.

Beanie (also known as a skull cap): tight-fitting knit hat.

Beret: a knit hat with a flat crown. It is narrower at the band so that the top can be pushed to one side.

Bucket: can be made of straw, felt or a soft knit, this hat has a flat crown and looks like a … bucket.

Bowler: this felt hat has a a round crown and a round brim. It is also known as a derby. Charlie Chaplin wore this type of hat.

Cloche: named after the French word for “bell” because of it’s rounded crown and brim that points downward, the cloche was popular in the 1920s but is regaining popularity.

Fedora: a felt hat or straw with an indented crown and a brim, usually with a hat band. Indiana Jones wore this kind of hat.

Floppy: a felt or straw hat with a rounded crown and a very wide brim.

Newsboy: a soft knit hat with a rounded crown and a bill at the front.

Trilby: same as a fedora, but with a narrower brim (these are on trend and worn by celebs such as Justin Timberlake, Johnny Depp and Brad Pitt).

Check out the great hats below for examples…


White House Black Market cloche wool hat, $48.00

Patrizia Fabri bucket hat, $135.00

Fedora hat, $4.99

Floppy brimmed hat, $39.99

Knit slouch beanie, $30.00

AllSaints knit beanie hat, $40.00

Mango beanie hat, $29.99

French connection trilby hat, $88.00

DKNY wool newsboy hat, $55.00

Scala leather newsboy hat, $65.00

Asos bowler hat, $35

Grey beret, $13


Now it’s time to find a hat that flatters you. Look below for your combination of bone structure, face shape, forehead and hair length to find your ideal hat. If you have a…

Petite frame: a large hat will overwhelm you, so look for a knit cap or one with a small brim (a beanie, beret, newsboy or cloche or a trilby).

Big-boned frame: a small hat will look out of proportion so go for the gusto! You can wear floppy hats, fedoras and bowlers. If you want to wear a beret or beanie, do it in a thicker knit or with a pattern to make a bold statement.

Round face: look for more angular styles, such as a fedora or a newsboy to balance out your features.

Square face: a more rounded hat such as a bowler or cloche will flatter your face.

High forehead: look for a hat with a deeper crown, such as the teal beanie above or a bowler.

Low forehead: a hat with a shorter crown, such as the white beanie or a newsboy, will flatter you.

Short hair: for women, wear something without a brim, such as a beanie, in order to look more feminine. Mens’ style hats on a short-haired woman will look too masculine.

Medium-to-long hair: you will great in hats with a brim, such as a fedora or beanie, or hats without, such as a cloche or a beret or a beanie.

If you are not sure about your features, hunker down in the hat section of a department store with a friend whose opinion you trust, and try on every type of hat they have until you find one (or more) that you like. Even if the store has 30 hats, it won’t take you more than a minute to try each one on. You’ll be so happy when you find the right one. And, everyone will be very impressed with your fashion sense because it’s so hard for most people to find a great hat. If you have any questions, let me know!

Illysia Neumann-Loreck

2 thoughts on “How to Find a Flattering Hat

  1. Is the Fedora hat really $4.99? That’s a deal if it’s not a mistake!

    Thanks for the good advice, I’m generally not a hat person but found your information useful.

    Hope all is well in MI! The children are getting so big and they are so good lookin’!


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