Retro Hairstyles With Pillbox Hats

Model Jessica Hart wears the pillbox and updo at a fashion event.

Photo: Matt Roberts/Getty Images Entertainment/Getty Images

One of the most iconic hats of the 1960s, the pillbox was a brimless number that went with many sophisticated hairstyles. Jacqueline Kennedy Onassis was a prolific wearer of the round, flat accessory, coordinating many with her ladylike ensembles and picture-perfect hair. However, the look is not just for old fogies, since this retro style occasionally graces the catwalks. Thus, scour the vintage shop and whip out the curling iron to create these mod looks at home.

Prim Pixie

For sexy 1960s cropped hair, look no further than the slicked-back pixie -- often seen on the likes of iconic model Twiggy. The mod hairstyle is cut with a side-swept bang, for an extra bit of hipster glam. Style the cut by massaging a pea-size amount of holding product through dry tresses. Part the hair along one side and slick the hair down, making sure to swoop the bangs close to the eyebrows. Select a Frisbee-shaped pillbox hat, maybe one with a feather, and situate it on one side of the head, close to the ear.

Sexy Side Roll

Another hairdo with mod roots is a pageboy -- which resembles an overgrown bob that just brushes the shoulders. A sexy side roll is what this Plain Jane haircut needs to get some retro appeal. Get it by massaging a quarter-size amount through your dry locks. Part the hair along one side, smoothing the less full section behind your ear. Then, train your tresses, flipping the hair up with a 1-inch curling iron. Create a large roll alongside your head and secure the barrel shape in place with bobby pins. Then boost the chic factor, placing a glitzy pillbox hat, say one that features a rhinestone pin, close to the opposite ear.

Fabulous Flips

Jacqueline Kennedy wore her pillbox hat with a flipped bouffant — a hairdo that was as integral to her style as her Chanel suits. For an iconic hairdo befitting of the first lady, part the hair along one side and curl the bottom of the tresses upwards with a 3/4-inch barrel, right above the ears. Brush the curls out to produce a softer flip before teasing the hair in the crown area. Delicately settle the soft pink woolen pillbox hat on your crown, about 3 inches away from your hairline, to complete the elegant look.

Elegant Twist

Pillbox hats are also a great accessory for an updo; a satin number with an alluring veil just reek with 1960's sophistication. To accommodate the hat, style your hair into a classic French twist. Gently tease the hair at the crown of the head to create a little bit of lift. Then, gather the hair at the nape of the neck and twist upward so the bulk of the hair is encased in a roll. Pin along the way and tuck the excess hair into the top of the roll for a clean look. Afterward, cover the front hairline with the hat, allowing the netting to fall seductively over the eyes.

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