These days, wearing a hat can be precarious from a fashion point of view. When do you wear it? When do you take it off? Are you occasion-appropriate? Is the hat dressing “up” your clothes, or dressing “down” a suit? Here are some of the most common classic men’s dress hat styles that you can wear with dressier clothes, and how you should wear them.
Style #1: Top Hats
Great for: Formal occasions and black tie events like horse racing.
The rundown: There’s no callback to dressier fashion days than the top hat, though it still finds plenty of use in modern times at formal events. Typically, you’ll wear a top hat with your finest black-tie suit, usually a tuxedo.
Wear with: A tuxedo.
Style #2: Western/ “Cowboy” Hats
Great for: The outdoors.
The rundown: Depending on your region, these hats may be considered more common headwear rather than an unusual accessory. The wide-brimmed western hat does best when you need coverage from the sun. You may look out of place if you wear it in a cool climate when wide-brimmed hats are a rarity.
Keep in mind that in some regions, a “western hat” might be appropriate for dress occasions like weddings.
Wear with: Casual pants, especially simple khakis like Flat Front Charleston Khakis.
Style #3: Fedoras
Great for: Jacket-wearing occasions and formal occasions.
The rundown: Many would consider the fedora a throwback to when wearing a hat was expected and not the unusual. But, a fedora can make a great “vintage” look at formal occasions, especially at events like weddings when you might spend some of the festivities outdoors.
Wear with: Formal jackets and suits, especially pleated trouser options like Super 100s Gabardine.
Style #4: Ascot Caps or Flat Caps
Great for: Evenings out, golfing, and more casual gatherings.
The rundown: The ascot—or a similar version, the “flat cap”—features a stiff brim in the front, pushing the entire look forward. Though it can be worn with more formal wear, like suits, it tends to have a sportier and more active look than the fedora. This makes it a good choice for outdoor events like golfing.
Wear with: Casual pants like Performance Dress Khakis in any color.
Style #5: Beanies
Great for: Outdoor situations from casual to dress, especially in cool weather.
The rundown: Depending on your climate and the local fashion culture, a beanie might look out of place and casual (in warm weather) or completely appropriate in a wide range of occasions (in cool weather). The beanie is a brimless hat that’s all about temperature control, which gives it a lot of fashion “leeway” as a matter of practicality.
Wear with: Cold-weather clothes. They fit very well with warm clothes like Wool Flannel Trousers. Remember to take them off indoors, where they are no longer practical!
Find the Outfit to Match Your Dress Hat at Berle
Depending on the occasion and the local fashion, a hat may be anything from casual to dress. What matters is how you wear it. Browse our tailored trousers to make sure you have something to fit every occasion, no matter which of these classic men’s dress hat styles you choose to wear!