How to Wear a Hat

Want to give your wardrobe a major boost? Take the plunge and buy yourself a hat. A well-chosen hat can add a strong statement to any outfit. If you want to punch up your wardrobe with a bold accessory, follow these tips to wear any hat with panache.

Method 1
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For Women: Great Hats for Spring and Summer

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    Wear a cloche hat. Cloche hats, or "flapper hats," are made either with or without brims.[1]
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    Try out a newsboy hat. Also called "paperboy hats," these hipster hats look great with both casual and professional wear. They are suitable for round and oval faces.[2]
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    Put on a giant sun hat. These hats have floppy brims and are great to wear during the daylight hours.[3] If you're wearing this type of hat in winter, choose a sun hat made of felt.
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For Women: Hat Choices for Fall and Winter

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    Wear a Victorian top hat. These hats are great with any outfit and are a great touch for a steampunk ensemble. Just keep the outfit simple since these hats are pretty elaborate.
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    Don a pork pie hat. Pork pie hats were invented in the Victorian period. Although they were traditionally worn by men, they look great on women as well.[4]
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    Deck yourself out in a beret. Knit and wool berets are great for the cooler seasons.[5]
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    Flaunt a fedora. These hats were also originally designed for men, but they look great with a woman's suit or even with girly dresses.
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For Men: Great Hat Ideas

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    Wear a flat cap. These hats look great with a suit or when you're wearing a large overcoat or trench coat.[6]
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    Put on a fedora. Humphrey Bogart and Frank Sinatra will have nothing on you when you put on your own fedora with either formal wear or business suits. However, fedoras are so versatile that you can also wear them with a polo shirt or T-shirt.
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    Try out a homburg. You've seen this hat in the Godfather movies, and lately you've seen it resurrected by Tupac and Snoop Dogg. Whether you're going for gangster or don, you'll look great in your homburg hat.[7]
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    Put on a pork pie hat. These hats were invented in the Victorian era for men and were named for their resemblance to a pork pie dish. Think Gene Hackman in The French Connection.
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    Go with a bowler hat. Think of Charlie Chaplin or an old 19th century New York City gangster. This hat looks great with a suit or with a nice shirt and a vest.[8]
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General Guidelines for Wearing a Hat

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    Pick a hat that matches your proportions. If you're petite, a huge wide-brimmed hat could totally overwhelm you. Instead of using size to make a visual statement, choose a hat with bold colors or vibrant trim instead.
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    Select a hat that flatters your hairstyle. You can wear a small hat to one side and twist a chignon on the opposite side. This effect also makes your neck appear longer.
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    Wear a hat that complements the shape of your face.[9]
    • If your face is round, choose a hat that has a broad brim to balance out the fullness of your face.
    • If your face is long, choose a softer design or something with movement, like feathers.
    • For a square-shaped face, choose an asymmetrical hat to balance the angle of your jawline.
    • People with heart-shaped faces are the luckiest. They can carry off almost any type of hat.[10]
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    Choose colors that flatter your skin tone. If you have a bold hat, tone down your makeup so that you don't look clownish.[11]
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    Connect your hat to your outfit. If you're wearing a dress with a peacock pattern, then try a hat with a jaunty peacock feather to unify the outfit. However, if your hat is bold, tone down accessories like jewelry so that you don't look garish.[12]
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    Secure your hat to your head. This advice may sound obvious, but the last thing you want to do is to spend your entire day clutching your hat against your head. Use thin elastic bands, ribbons or combs to make sure that your hat stays in place.
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Expert Q&A

  • Question
    What is the best hat for my face shape?
    Neepa Sikdar
    Neepa Sikdar
    Personal Stylist
    Neepa Sikdar is a Personal Stylist and the Founder of Accessible Style. With 18 years of fashion experience, she specializes in working with female leaders to develop their style through personal styling, brand styling, and online styling. She also coaches women on personal style through her membership program. Neepa has worked with brands such as Nordstrom and J. Crew and has been featured in publications such as Business Insider. She holds a BS in Economics and English from Rutgers University and trained in styling through Fashion Institute of Technology.
    Neepa Sikdar
    Neepa Sikdar
    Personal Stylist
    Expert Answer
    Fedoras look good on round or square faces; newsboy hats look good on round or oval faces; baseball hats look good on oval and round faces; cowboy hats look good square faces; and floppy hats look really good on oblong faces.
  • Question
    What face shape works well with a floppy hat?
    Neepa Sikdar
    Neepa Sikdar
    Personal Stylist
    Neepa Sikdar is a Personal Stylist and the Founder of Accessible Style. With 18 years of fashion experience, she specializes in working with female leaders to develop their style through personal styling, brand styling, and online styling. She also coaches women on personal style through her membership program. Neepa has worked with brands such as Nordstrom and J. Crew and has been featured in publications such as Business Insider. She holds a BS in Economics and English from Rutgers University and trained in styling through Fashion Institute of Technology.
    Neepa Sikdar
    Neepa Sikdar
    Personal Stylist
    Expert Answer
    Pretty much anyone can pull off a floppy hat! However, they look especially good on individuals with an oblong face shape.
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Warnings

  • Be courteous if you're wearing a hat to an outdoor event in a stadium. Make sure that your hat isn't so large that you obstruct the view of someone sitting behind you.
    ⧼thumbs_response⧽
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References

  1. ↑ https://vintagedancer.com/1920s/1920s-hats-styles/
  2. ↑ Neepa Sikdar. Personal Stylist. Expert Interview. 11 February 2022.
  3. ↑ https://www.harpersbazaar.com/uk/fashion/fashion-news/a22497329/how-the-oversized-straw-hat-became-summers-key-accessory/
  4. ↑ https://www.hatsinthebelfry.com/blog/how-to-wear-a-pork-pie-hat.html
  5. ↑ https://www.glamour.com/story/how-to-wear-a-beret
  6. ↑ https://www.gentlemansgazette.com/flat-cap-newsboy-hat/
  7. ↑ https://www.gentlemansgazette.com/homburg-hat-history-style/
  8. ↑ http://artofmanliness.com/2008/03/01/bringing-back-the-hat/
  9. ↑ https://40plusstyle.com/how-to-choose-hat-for-your-face-shape/
  1. ↑ http://www.dailymail.co.uk/femail/article-1194180/How--wear-hat.html
  2. ↑ Neepa Sikdar. Personal Stylist. Expert Interview. 11 February 2022.
  3. ↑ Neepa Sikdar. Personal Stylist. Expert Interview. 11 February 2022.

About This Article

Neepa Sikdar
Co-authored by:
Neepa Sikdar
Personal Stylist
This article was co-authored by Neepa Sikdar. Neepa Sikdar is a Personal Stylist and the Founder of Accessible Style. With 18 years of fashion experience, she specializes in working with female leaders to develop their style through personal styling, brand styling, and online styling. She also coaches women on personal style through her membership program. Neepa has worked with brands such as Nordstrom and J. Crew and has been featured in publications such as Business Insider. She holds a BS in Economics and English from Rutgers University and trained in styling through Fashion Institute of Technology. This article has been viewed 103,858 times.
3 votes - 100%
Co-authors: 31
Updated: March 14, 2023
Views: 103,858
Categories: Hats
Article SummaryX

To wear a hat, try to choose one that matches your proportions. For example, if you're petite, an over-sized or wide-brimmed hat may take over your entire look. Similarly, pick a hat style that flatters the shape of your face and skin tone. Also, evaluate what you're wearing and select a hat that unifies the outfit and complements the overall style you're going for. For tips on wearing specific types of hats, read on!

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