I first fell in love with the circle skirt as a six-year-old watching “The Sound of Music.” Admittedly I have very little in common with Maria Von Trapp, but one look at the cinched waist and volumnious skirt I knew that I met my style twin. Be warned, the circle skirt isn’t for everyone. At five-foot-nine, I have an average figure with a narrow waist. This look is really hard to pull off if you have a thick waist or are exceedingly top heavy. Instead of giving you the look of having an hour-glass figure, it may make you look bigger than you are which is totally unflattering. Here are three ways to wear the totally timeless 50s circle skirt.

1. Vintage Vixen
Your circle skirt paired with a slim top, cropped cardigan, and kitten heels will even make Mad Men’s Don Draper take notice.

2. The Rocker
Paired with a pair of slim flats and a rock star t-shirt, a circle skirts fit the bill for country and city girls alike.

3. Totally Luxe
Don’t be afraid to go totally luxurious in your circle skirt. Think opera gloves, clutch purses, pearls, rhinestones, and a pair of statement heels. It’s your time to see and be seen.

This slideshow requires JavaScript.