Ways to Wear a Vintage Hat

Kastle Waserman
by Kastle Waserman

I long for the days when ladies wore hats with every outfit. Sadly, that hasn't happened since the midcentury era. Now hats are a novelty but they are also an easy way to add a pop of personality to any outfit. Do you need a little encouragement? Here are some fun ways to wear a vintage hat.

I bought this vintage hat on Etsy. It's a 1960's bubble hat designed by renowned milliner Lilly Daché. The style is a little over-the-top (even for me!) with its headful of fabric cutouts that resemble flower petals. But I love that it's exaggerated and has movement. It's definitely a statement piece and gave me a fun styling challenge to figure out ways to wear it without looking comical.

A Vintage Hat with a Little Black Dress

The great thing about the little black dress is it's just a blank canvas to let your accessories shine. It's perfect to pair with a vintage hat in just about any color or style. I chose a classic black shift dress and added a long beaded necklace. The look gives some Audrey Hepburn in "Breakfast at Tiffany's" vibes. This outfit's simplicity could work for a nightclub, a happy hour or out to dinner without worrying that the hat is too much.

A Vintage Hat with Jeans and a T-shirt

The basic jeans and tee could use a refresh. Pair it with a bold hat and you'll have a unique look with a stylish edge that will stand out from the crowd. Go with a playful t-shirt such as a band logo, a graphic print or a design such as stripes to add even more interest. This look would be appropriate for a concert or a casual daytime outing with friends.

A Vintage Hat with Another Vintage Piece

While some vintage enthusiasts have no problem wearing head-to-toe vintage and never feel it looks like a costume. Others may just want to incorporate a piece or two into their modern wardrobe for a bit of spice. If you're in the latter category, try pairing your vintage hat with one other vintage item, such as a top, skirt or handbag.

Since my hat is from the 1960s, I went with a '60s-era top. The floral design ties in with the fabric petals on the hat to create a coordinated look. Then I tied in the black color with a classic black pencil skirt, which makes the silhouette simple and chic. A pop of color in the shoes keeps the fun spirit of the look going. This look could be worn on a date night, to a party or out dancing.

Start With a Hat That Works for You

If you're new to vintage or bold styling, you don't have to start with such a statement hat. Try some simple shapes you feel comfortable with – a wide-brimmed hat for summer or classic fedora. I love vintage hats because they are usually one-of-a-kind since not that many have survived over the decades. Those that have are usually quality pieces. Hats are an easy way to give your wardrobe a little boost of unique styling.

Can you think of some ways to wear a vintage hat? Check out more of my vintage looks on my blog StilettoCity.com and Instagram page.

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