You Can Leave Your Hat On…


Hats! There is no article of clothing more expressive than a hat. When a person dons a hat, it is the first thing you notice when you see her/him. Whether practical or decorative, a hat is an extension of one’s self. You can tell a lot about a person by his or her hat.

To say that I have a passion for hats would be an understatement. I own dozens of hats from fashionable vintages to practical knits, and I will never own as many as I would like to! I even live in Connecticut’s Hat City. It saddens me that the days when a person didn’t leave his/her house without a hat have long passed. Once a fashion necessity for women, the hat has fallen into obscurity like stockings with seams, or is simply used for warmth. For men, hats have become a means of hiding receding hairlines whilst simultaneously expressing their devotion to a particular sports team. So sad. I have hope for the hat, though. Events such as the Royal Wedding and the Kentucky Derby remind us that hats are fun!

A lot of people say, “I don’t look good in hats.” To that, I say, “You just need to find the type of hat that is right for you.” You can’t all be as lucky as me and look good in pretty much any hat (part genetics, part personality). But don’t dismiss the possibility of finding a hat that suits you. There so are many styles to choose from that it can be dizzying.

Things to consider when selecting a hat.

Choose a hat that:

1).  You feel confident and comfortable wearing

2).  Suits your personality and style

3).  Frames and complements your face

Some Types of Hats

Men, please ditch the baseball caps once in a while and bring out your inner Sinatra. Take a tip from the characters on shows like Mad Men. So, you can’t all look like Donald Draper, but you can come a little closer if you wear a fedora or trilby hat. It exudes confidence and sophistication. Baseball caps, on the other hand, lump you together with UCONN students and the countless undistinguishable men people meet on a daily basis. I once asked out a guy because he looked so freakin’ hot in his fedora!

Baker Boy Caps, a.k.a. Newsboy Hats: They are timeless, ageless, and sexless. My grandfather, my uncle, and my brother all look handsome in their newsboy hats. Three generations of men, same hat. The newsboy hat also tends to be my personal go-to hat. They are adorable on women and get many compliments.

Cowboy Hats: Guys, unless you are in Texas, you should not wear a cowboy hat. Even then, it’s debatable. Women, it is possible to look cute in a cowboy hat, but difficult to pull off. It’s 70% style and 30% attitude when it comes to this hat. You need to be confident and know you look cute.

Some more traditionally “male” hats: Bucket Hat (Gilligan), Fedora/Trilby (Sinatra, Depp, Michael Jackson), Porkpie Hat (jazz musicians), Panama Hat (popularized by Teddy Roosevelt), Fedora (Bogart, Indiana Jones), Bowler/Derby Hat (Chaplin, Princes William and Harry), Boonie (Bill Murray in Caddy Shack), Cuban Revolution Hats (Che Guevara, Fidel Castro, and Bruce Wingate), Hunting Hat (Holden Caulfield; a.k.a. ‘people shooting hat’).


Now that you know a few of the many hats that were originally designed for men, you can imagine there are a plethora of options for women; it’s overwhelming.

Go Vintage! My favorite hats are those that I’ve found at tag sales, art shows, clothing swaps, vintage clothing stores, and my grandmother’s closet. From 1920s cloche hats to 1950s pill-box hats, the varieties seem endless. Buy a hat that you will actually wear (or give to me). It’s a sin to let a good hat sit in your closet.

Faux Vintage: If previously loved clothing is not your thing, there are many stores that sell hats that resemble looks from the past. One of my favorite cloche hats came from Target. My newsboy cap came from the dollar store (It’s my favorite, and I’ve owned it for 7 years).

Sun Hats: I cannot stress enough the necessity for a sun hat. Not only does it shield your precious eyes from the sun’s harmful rays, but it also protects your beautiful face from premature aging while you get your essential vitamin D. People always think I’m far younger than I look, and I intend to keep it that way!

Most women look cute and sexy when we wear a man’s hat. It’s like wearing a man’s dress shirt with nothing else but your panties and knee socks – Risky Business-style. However, do not go over the top and combine your pin-striped gangster-style hat with a matching pin-striped jacket. Unless it’s your usual look or Halloween, it looks tarty and contrived. Highlight your personality, don’t drown it with pretension.

Make yourself memorable. Show off your awesomeness. Wear a hat! Happy shopping!!


All photos by Christine Molnar.


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  2. Wow, I was unaware that hats can be expressive. I think I will buy my husband a country music cowboy hat online because he feels confident wearing one. Since he’s from Texas, I’m sure that he’ll pull it off.

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