What Should Guys Wear With Newsboy Caps?

Pairing your newsboy cap with a vest gives you an outfit with plenty of vintage flair.
Pairing your newsboy cap with a vest gives you an outfit with plenty of vintage flair. (Image: Jupiterimages/Goodshoot/Getty Images)

While the newsboy cap may have originally become popular with England's newsboys and working class men, the modern incarnation can be a stylish accessory for every man. As with any hat, finding the right outfit to pair it with is key -- and the newsboy cap is one of the easier hats to style because you can wear it with everyday pieces in your wardrobe or dress it up for more formal occasions. Due to its charm and versatility, there's bound to be at least a few items in your closet that can work well with a newsboy cap.

Go Casual

Because it was a hat traditionally worn by working-class men, the newsboy cap makes an ideal accessory for a casual outfit. You can wear it with your favorite cargo pants or khakis – or even a pair of shorts when the weather warms up. When it comes to shirts, wear your newsboy hat with a basic tee shirt or go for a slightly more polished look with a collared polo shirt. To make sure that your casual look is stylish and put together, try to match your hat with at least one element in your outfit. For example, if your newsboy cap is a light tan color, pair it with light tan cargo shorts to create a matching look.

Wear Jeans

Jeans definitely have a casual feel, but they also work well for an evening out – and they’re an ideal piece to pair with your newsboy cap. If you want your outfit to have a dressed-up feel, opt for jeans in a dark wash. For a relaxed look, choose a lighter wash. When it comes to fit, newsboy hats tend to work best with slim-cut jeans as the close fit of the pants help to balance out the added volume on top. You can wear almost any shirt with your jeans and hat, but an oxford shirt, whether dress or casual style, will give you the most polished look.

Add a Vest

A newsboy cap can have a vintage feel, so you may want to go all out and pair yours with another item that has old-fashioned flair – a vest. While vests are often worn as part of more formal outfits, you can pair one with your favorite jeans and hat to give them a more sophisticated look. Under the vest, wear a button-down shirt or go more casual with a tee or a Henley shirt. A newsboy cap-and-vest combination typically looks best if the two pieces match or are similar, so choose a vest as close to your hat in material and color as possible.

Dress It Up

If you’re the kind of guy who likes to look a little more put together, dress up a newsboy hat by pairing it with a more formal outfit. Wear your newsboy hat with a suit and tie – just make sure that it matches the suit to keep your look polished. You can also skip the suit jacket and pair the hat with dress pants, a button-down shirt, a tie and a cardigan. A newsboy cap also works well when you wear a sweater over your shirt and tie.

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