No One Does Rom-Com Dressing Better Than Cameron Diaz

Amanda Woods may be out of her element when she's slipping around the snowy English countryside, but she soon finds her footing—and a handsome English beau—with the help of some charmingly cozy fits. For a romantic outing in the middle of winter (who decided to put V-Day in February, anyway?) you can't go wrong channeling her style with a long shearling coat and matching white knits.

But for what she thinks is a romantic dinner for two, she taps into that boss-babe confidence in a glam black-and-white ensemble, featuring a plunging sheer top, white pencil skirt and glitzy statement belt.

Although I'm using an admittedly loose definition of "rom-com" when referring to 1994's The Mask, there's no denying the fact that Diaz's looks in the film were s-s-s-s-smokin'. For her first-ever movie debut, she sauntered onto the screen in a skin-tight red dress—somewhat softened by a slouchy jacket adorned with florals. If you ask me, it's the ultimate V-Day ensemble, especially if you swap out the rosettes for a red heart pattern.

While it's hard to compete with Julia Roberts at her wild-haired prime, Diaz proved to be a worthy opponent in the battle for Dermot Mulroney's heart. As the pearl-donning Kimberly Wallace, Diaz brought a playful bubbliness to her old-money aesthetic that her betrothed—and I, for that matter—couldn't help but fall in love with. Cue the sunny shift dresses, playfully patterned silk scarves and subtle heart-accented accessories.

Everybody remembers that cringe-worthy "hair gel" scene, but if there's anything about Mary in There's Something About Mary, it's how well she does cute and casual girl-next-door style. Her wardrobe was full of simple separates that said, "I don't have to try too hard to look adorable." Think: easy, minimalist and effortless. All it requires is the perfect cardigan.

As a party girl who could give Carrie Bradshaw a run for her money, Diaz's character in The Sweetest Thing had a lineup of dance floor looks worthy of the VIP list. Fun, flirty, free-spirited—we're talking one-shoulder tops, sky-high stilettos and one very low-rise pair of red pants. While you don't have to go as skin-baring as she does, it's definitely not a bad formula if you're hoping to turn heads (and possibly meet the love of your life) on a night out.