21 Best Vintage-Inspired Updos

Playful Drive-In Girl

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A twisted front roll hairstyle paired with a side ponytail is fun, flirty, and perfect for a rockabilly-inspired summer look.

a) Twisted front roll for a structured, stylish updo
b) Fitted crop top and high-waisted shorts for a playful pin-up aesthetic
c) Holding roller skates at an old-school drive-in for a nostalgic setting

Hollywood Rockabilly Glam

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A deep side part with smooth sculpted waves creates a glamorous, red-carpet-ready rockabilly style.

a) Smooth, sculpted waves for a sleek and polished look
b) Floor-length satin gown for maximum Hollywood elegance
c) Vintage red carpet setting to enhance the old-school glamour

Fierce Rockabilly Biker Chick

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For those who love an edgy and rebellious vibe, a voluminous quiff paired with a leather jacket and high-waisted pants creates a fierce rockabilly biker aesthetic.

a) Voluminous hair swept up into a retro quiff for a bold statement
b) Leather jacket and combat boots for a tough, vintage-inspired look
c) Sitting on a vintage Harley-Davidson to complete the biker aesthetic

1940s-Inspired Faux Bob

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A faux bob styled with large curls is a perfect way to create a vintage 1940s look with elegance and charm.

a) Faux bob with soft, structured curls for a polished finish
b) Vintage polka-dot dress for a classic old-school appeal
c) Pearl necklace and a tea-sipping moment at an old-fashioned café

Pin-Up Camera Starlet

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A cherry-print playsuit, high victory roll, and curled ponytail create a playful and flirty rockabilly style, perfect for capturing vintage nostalgia.

a) High victory roll for a structured, retro-inspired updo
b) Curled ponytail to add a fun and lively touch
c) Posing playfully with a vintage camera in a classic American diner