The Most Fashionable It Girls (and It Boys) Are Now Adopting "Personality Dressing" Rather Than a Uniform Style.

      Wearing a uniform and adhering to it represents the high-step-count, asleep-by-9:30 PM version of yourself. In contrast, personality dressing takes on a more eclectic approach, where rather than establishing a distinct look, silhouette, or color palette, you continuously mix things up. During his recent promotional tour for the sci-fi thriller Disclosure Day, Josh O’Connor has showcased all the traits of a personality dresser, appearing in a variety of outfits that don’t conform to one mood or theme, but alternate between preppy and sophisticated (the common thread being that all outfits are stunning and often designed by Dior). The key takeaway is that while his outfits have channeled various characters—such as the millennial dad—they have remained true to his personal style: a scruffy yet suave aesthetic, curated by stylist Jason Bolden. This also applies to someone like Zoë Kravitz, whose casual wardrobe typically includes The Row, yet she infuses her unique personality (or personalities) into those refined, luxurious basics. This form of dressing is an art, one that you can cultivate so that your clothing, while suggesting different facets of your personality, consistently reflects who you are. Keep scrolling to see and shop the various personas of three A-listers that can ignite your own experimentation. Celebrities Defining 'Personality Dressing' in 2026: Josh O'Connor

      1. Renaissance Prep

      Style Notes: Starting with the Renaissance prepster, who was once fond of Polo Ralph Lauren (which is currently experiencing its own revival) and was never seen without boat shoes. The 2026 version, as described by O’Connor's stylist, Jason Bolden, includes a collar-popped canary yellow shirt by Dior, tailored black trousers, and "fancy" loafers (featuring a statement buckle, vibrant color, or intricate fabric). Shop the Trend:

      Polo Ralph Lauren

      Cable Knit Cotton Quarter Zip Jumper

      

      JAMIE HALLER

      Essential Cotton and Silk-Blend Shirt

      Free People

      Yachting Day Boat Shoes

      2. Millennial Dad

      Style Notes: The "millennial dad" attire—regardless of actual parenting status—consists of several key elements: retro tracksuit bottoms, technical trainers (think Salomon or Mizuno), and a practical blouson jacket, all in bold colors that suggest a move away from cream tones. The millennial dad favors functional yet stylish accessories: a slogan baseball cap, a branded tote bag from a coffee shop, and a reusable travel mug (typically from Chilly’s or Yeti). Shop the Trend:

      Lululemon

      License to Train Textured Nylon Mid-Rise Pant

      Veronica Beard

      Circe Bubble Jacket

      Salomon

      Xt-6 Unisex Trainers

      3. Smooth CEO

      Style Notes: A CEO with a personal style to match their charisma? That’s appealing, and it certainly excludes polyester tailoring. O’Connor's interpretation was a custom-made Dior suit, complemented by a vintage pin from Tiffany & Co (swoon!), presenting a modern tuxedo look: a cream jacket paired with a white dress shirt, collar turned up, and a powder-blue tie. Fresh is an understatement. Shop the Trend:

      Tiffany & Co

      Elsa Peretti® High Tide Brooch in Sterling Silver

      With Nothing Underneath

      White Poplin Dress Shirt

      Bustle and Bow

      Silk Ribbonette

      Zoë Kravitz

      1. Thrift-Store Hottie

      Style Notes: Zoë Kravitz’s usual ensemble is head-to-toe The Row. However, she sometimes delves into Saint Laurent. I like to call this particular style "thrift-store hottie": pairing a vintage fur-trimmed cardigan with contemporary knife-point court shoes. It’s an easily adaptable look for real life, blending "cutesy" twinsets with lace slip skirts, stilettos, and oval-shaped sunglasses. Shop the Trend:

      Saint Laurent

      Amalia 110 Patent Leather Slingback Pumps

      MANGO

      Cross-Over Lingerie Skirt With Slit

      Jimmy Fairly

      The Cinnamon

      2. 2026 CBK

      Style Notes: Even Kravitz can't resist Carolyn Bessette Kennedy's minimalist allure. Her outfit—a white shirt, black kick-flare trousers, a fluid trench coat, and chisel-toe boots—is a subtle homage; an everyday look that maintains a polished aesthetic without requiring a heavy tortoiseshell headband. Shop the Trend:

      M&S

      Pure Cotton Girlfriend Shirt

      Ninetypercent

      Kick Flare Pants

      Khaite

      Nevada Leather Ankle Boots

      3. Final Boss

      Style Notes: The actor-director turns to just one label for evening attire: Saint Laurent. This glamorous yet grounded tonal brown outfit features a second-skin turtleneck, high-waisted pleat-front trousers, and flat shoes (ideal for