How Your Favorite Romantic-Comedy Characters Would Do Their Makeup in 2018

Updated 11/30/18

Sometimes, nothing feels better than a night of chilling at home with a glass of wine, watching your favorite romantic comedies, and swooning after the leading ladies' iconic looks. Consciously and unconsciously, rom-com queens like Meg Ryan and Julia Roberts have influenced so many of our beauty choices. The first time I ever applied pink lip gloss, all I wanted was to look like Elle Woods.

If we could, we'd go on a Sephora shopping spree with Vivian Ward from Pretty Woman and Jennifer Lopez's character Mary Fiore from The Wedding Planner, but since that's not exactly in the cards, we'll settle for this game of make-believe instead. Read on to discover our 2018 interpretations of unforgettable rom-com makeup routines—from classics like Diane Keaton's titular character in Annie Hall and Meg Ryan's Annie Reed in Sleepless in Seattle to 21st-century blockbuster roles like Reese Witherspoon's Elle Woods in Legally Blonde.

If these onscreen icons were to shop for makeup today, this is what we think they'd buy.

Mary Fiore in The Wedding Planner

The Setting: Early-2000s San Francisco. Wedding planner Mary Fiore (Jennifer Lopez) has been nuptial-obsessed since early childhood but has become so focused on her career that romance has completely fallen by the wayside. She spends her nights alone in her apartment eating takeout and watching Antiques Roadshow. Mary is professional and ambitious, hoping to make partner at her firm.

The Vibe: Polished, meticulous, and business-like. Mary is the girl who cleans her apartment and folds her napkins every night, and she treats her brows, lashes, and lip liner with equal precision and poise.

In Her Words: "I am a goddamn professional!"

The Products:

Clinique Even Better Makeup Broad Spectrum SPF 15 $29
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Benefit Cosmetics Precisely, My Brow Pencil Ultra-Fine Shape & Define $24
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Nars Velvet Matte Lip Pencil $27
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Annie Reed in Sleepless in Seattle

The Setting: Early-2000s Baltimore, Seattle, and New York. Hopeless romantic Annie Reed (Meg Ryan), a reporter in Baltimore, is listening to a love-advice radio show when widower Sam Baldwin (Tom Hanks) calls in. Upon simply hearing his voice, Annie falls for him, even though they've never met and she is engaged. So Annie writes Sam a letter asking him to meet her at the Empire State Building on Valentine's Day, hoping it might lead to something.

The Vibe: Romantic, understated, and moody. Anything to make those big eyes and softly downturned lips look even poutier.

In Her Words: "Destiny is something we've invented because we can't stand the fact that everything that happens is accidental."

The Products:

Ciate London Magic Pout Potion Lip Plumping Primer $20
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Charlotte Tilbury Eyes to Mesmerize Cream Eyeshadow $32
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Marc Jacobs Velvet Noir Major Volume Mascara $26
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Vivian Ward in Pretty Woman

The Setting: The late '80s/early '90s in the seedy side of Hollywood and the ritzy side of Beverly Hills. Vivian Ward (Julia Roberts) is a prostitute on Hollywood Boulevard; Edward Lewis (Richard Gere) is a high-powered businessman who picks her up on a lark. The two fall hard for each other, despite all the unlikely odds.

The Vibe: Both before and after Vivian's transformation from hooker to ingenue, her aesthetic is flashy, unapologetic, and free-spirited.

In Her Words: "I wouldn't say I'm a planner. I would say I'm a kinda fly-by-the-seat-of-my-pants gal. You know, moment to moment."

The Products:

E.l.f. Eyeshadow Palette $15
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Nyx Matte Liquid Liner $5
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Maybelline Color Sensational Creamy Matte Lip Color $8
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Anne Hall in Annie Hall

The Setting: Manhattan, New York, in the 1970s. Anne Hall (Diane Keaton) is a struggling nightclub singer with a quirky personality, trying to navigate the dynamics of her relationship with cynical comedian Alvy Singer, her polar opposite. 

The Vibe: Playful and eccentric. Annie Hall's minimalistic makeup aesthetic complements her iconic androgynous menswear-inspired clothes.

In Her Words: "La-dee-da, la-dee-da."

The Products:

Rodin Olio Lusso Luxe Lipstick $38
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Milk Makeup Lip + Cheek $24
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RMS Beauty Eye Polish $28
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Elle Woods in Legally Blonde

The Setting: Early-2000s Los Angeles and Boston. Ditzy but unexpectedly brilliant Elle Woods (Reese Witherspoon) has the perfect Southern California life until her snobbish boyfriend dumps her for a classmate at Harvard Law School. So Elle gets into Harvard herself to win him back. 

The Vibe: Sparklingly positive, frilly, and pretty fancy, though deeper than she appears. She's no doubt a stickler for well-made formulas and beauty-obsessed. Even her résumés are pink and scented.

In Her Words: "Whoever said orange was the new pink was seriously disturbed."

The Products:

Estée Lauder Double Wear Stay in Place Makeup $42
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Too Faced Sweethearts Blush $30
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Dior Addict Ultra-Gloss $30
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Monica Wright in Love & Basketball

The Setting: The late '90s/early 2000s in Los Angeles. Tough girl Monica Wright (Sanaa Lathan) and her childhood friend Quincy McCall (Omar Epps) both aspire to be professional basketball players. Monica is fiercely competitive but sometimes her emotions get the best of her, especially as, over the years, she and Quincy begin to fall for each other, only to have their diverging basketball careers threaten to pull them apart.

The Vibe: Tomboyish. Monica has no time or interest in a cumbersome makeup routine.

In Her Words: "I'd rather wear a jersey than an apron."

The Products:

Aquaphor Lip Repair $4
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Wet n Wild MegaGlo Makeup Stick Conceal and Contour $4
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Essence Lash & Brow Gel Mascara $3
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Princess Buttercup in The Princess Bride

The Setting: The mythical land of Florin, sometime in the Middle Ages. Stunningly beautiful peasant-turned-princess Buttercup (Robin Wright) and her one true love, farm boy Westley (Cary Elwes), are tragically separated. They embark on a dangerous fairytale adventure to reunite and save Buttercup from her unwanted marriage to stick-in-the-mud Prince Humperdinck.

The Vibe: Romantic, delicate, and classic. Buttercup is the fairest maiden in the land and your classic damsel in distress.

In Her Words: "You can't hurt me. Westley and I are joined by the bonds of love. And you cannot track that, not with a thousand bloodhounds, and you cannot break it, not with a thousand swords."

The Products:

Kjaer Weiss Cream Blush Compact $56
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Rosebud Perfume Co. Smith's Rosebud Salve Tube $6
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Glossier Lash Slick $16
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Next: Don't miss nine wise tips from Byrdie readers over 40.

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