R29’s Fall Lookbook: Sir John Sets The Tone With Five Power Looks

Move over, butter skin and blurred lips — fall is upon us, and with it, a new makeup mood to match. The shifting season is on the mind of celebrity makeup artist and Medicube creative director Sir John (known for painting famous faces like Beyoncé, Naomi Campbell, Zendaya, and Serena Williams), who we’ve tapped to dream up five creative interpretations of fall beauty for the R29 Lookbook. 

“People always think that spring is renewal, but I feel like fall is really the ultimate reset and realigning,” he tells us on set. “It's kind of back to basics in a way. And I think it always makes us a bit more present. Sometimes after the summer, we need something that's grounding.” Ahead, you’ll discover five inspirational looks that are defining fall 2025 — and will have you running to recreate them ASAP. To call them “trends” is a veritable understatement; they’re a whole vibe, but made DIY-able. From retro-meets-modern to a 2.0 take on cat eyes, keep scrolling for five makeup moments straight from the Sir John cinematic beauty universe, just for us.

Hollywood silver screen sirens are an endless source of beauty inspiration, and here, Sir John presents them in a moody fall palette. “This is the ‘90s does the ‘40s,” says Sir John of this layered interpretation. “I love the glamour of the Hollywood Regency Era: It was just so ultimate, feminine, and almost exaggerated in the features.” For this look, everything — eyes, cheeks, lips — is subtly dialed up. Think: a face card that pops on camera, but with the effortless ease of an ingénue. 

On set, Sir John used Make Up For Ever’s Artist Color Pencils to softly line and define eyes, before using individual lashes on the bottom for a doll-like effect. “If you don't feel comfortable with individual lashes, use two different mascaras [for the top and bottom],” he says, name-checking L'Oreal Telescopic Mascara. Then, opt for a volumizing formula for both the upper and lower lashes to add falsie-like drama. (“Think of the separating mascara as your primer,” he explains.) A touch of terracotta blush, like Danessa Myricks Yummy Skin Blurring Balm Powder Blush in Jubilee sculpts cheekbones for definition worthy of the big screen.

“These aren't uptown girls — they’re downtown women,” says Sir John of this bold, unapologetically glam moment. Evoking icons like Debbie Harry and Grace Jones, this look is all about sculpted, high-octane color, and skin that has a hint of gleam. (Perhaps from breaking a sweat on the dancefloor?) “I love the juxtaposition between frost and shimmer,” says Sir John. “Bring a little disco into the daytime.” To get the look at home, blend a dark navy shadow in the crease for a smoky effect, and apply a highly-pigmented matte shadow (like Violette_FR’s Yeux Paint in Dieu Bleu) in the center of the lid for a pop of color. Finish with a bold red lip — Sir John used Fenty Beauty’s Stunna Lip Paint in Uncensored — topped with a juicy, clear gloss for can’t-look-away shine.

“These aren't club girl pearls,” says Sir John of this ethereal, luminous look. “I added four on the lid to give a nice little bit of a light reflection, but it's all very elevated.” A soft wash of shimmery champagne-silver on lids, like Charlotte Tilbury’s Eyes to Mesmerize in Champagne, serves as a perfect backdrop for the pearls (Half Magic makes similar ones that are easy to apply and don’t require glue), while glowy skin takes anything but a backseat. (We love Saie’s Glowy Super Gel, either worn alone or mixed with foundation for a lit-from-within effect.) Sir John prepped skin with Medicube’s Medicube Kojic Acid Turmeric Overnight Mask and Collagen Niacinamide Jelly Cream to deliver this glass-skin effect.

Meet the cat eye’s sophisticated sister who’s back from studying abroad in Paris. Feathered out and blended, but still with a lifting, eye-opening winged shape, this liner look is giving us all the feels. An inky, jet-black gel liner is the way to go here — Sir John used Inglot’s AMC Eyeliner Gel, a makeup artist best-kept-secret — to create a smooth shape that won’t budge once it’s set. Keep the focus on your eyes by creating a “baby soft” nude lip. Sir John’s recipe: “We're overlining and then going lighter in the center — it's the ultimate contour,” he explains. Bring lashes to life with generous coats of L’Oréal Voluminous Mascara (the limit does not exist) and add a hint of flush to cheeks with your favorite rosy blush.

Make your own limelight this season by adorning your lids with scintillating sparkle that commands attention. “I always say, beauty is a feeling,” explains Sir John, who combined metallic lids with equally mesmerizing lips for a look that brings a serious dazzle factor. To recreate this look at home, try a burnished metallic shadow like Lisa Eldridge’s Liquid Lurex in Charcoal and layer an ultra-reflective glitter like Makeup By Mario’s Master Crystal Reflector in Citrine and Quartz for multidimensional sparkle. A color-shifting, prismatic lip topper like Rem Beauty’s Plumping Lip Gloss in Fembot seals the deal.