Valentine's Day Outfits Worthy of Bettie Grable, Marilyn Monroe, Dita Von Teese, and Your Own Cute Self

Holidays are one of the few excuses we have, as a society, to whole-heartedly embrace the cliché. Sparkles on New Year's Eve? A witch costume on Halloween? You're not a lemming, you're just adorably caught up in the spirit of things.

As we plan our Valentine's Day outfits, whether for our annual Love is Dark Like My Black Black Heart anti-Valentine's bash, or for an over-the-top, oysters-and-champagne dinner for two that'll have onlookers rolling their eyes, this is one day when channeling a pinup girl — whether you're a Bettie, a Marilyn, or a thoroughly modern Dita — is wholeheartedly okay.

A wiggle dress

It’s called a wiggle dress, but how you move in it is up to you.

Masuimi Dress in Deep Plum, $98, pinupcouture.com

Tattoo-inspired earrings

Kitschy, plasticine, and weirdly reminiscent of those tacky-but-romantic tattoos sailors used to get on their massive biceps.

Red True Love Stud Earrings, $6, unique-vintage.com

High-waisted red jeans

The better to shimmy in, my dear.

Gotta Jet Set Jeans in Red, $59.99, modcloth.com

A cropped sweater

It’s all so casual until you wear a bullet bra underneath.

Kimchi Blue Shaker Cropped Sweater, $29, urbanoutfitters.com

Tight top, low neckline

Optional: Scarlett O’Hara’s 17-inch waist.

Peasant Top in Red, $56, pinupcouture.com

A pastel romper

Like something Dita Von Teese might wear during her off hours — does she even have off hours?

Rachel Pally Zenobia Romper, $211, shopbop.com

A crinoline

Instantly make any skirt more pinup-worthy — and about 50 percent bigger — with a cloud-like petticoat underneath.

Va Va Voluminous Petticoat in Cotton Candy, $59.99, modcloth.com

Lolita sunglasses

Lolita wasn’t exactly a pin-up girl, but she sure knew how to work her charms. Ew.

Wildfox Couture Lolita Sunglasses, $189.00, urbanoutfitters.com

A modernized wiggle skirt

Denim and leather make this skirt as city-slicker as they come.

Denim and Leather Look Wiggle Midi Skirt, $41.67, asos.com

A demure-ish dress

You don’t have to show a lot of skin to join the pin-up club.

Full Steam Ahead Dress, $109, shabbyapple.com

A comfy top

Spanx and heels not your thing? Channel the spirit of the day in a cozy sweatshirt that lets Marilyn do most of the talking.

Worn By Pin Up Crew Neck Sweatshirt, $46.30, asos.com