The Most Stylish It Girls (and It Boys) Are Now Adopting "Personality Dressing" Over a Standard Look.

      Donning a uniform embodies a high-step-count, asleep-by-9:30 pm version of yourself. In contrast, personality dressing adopts a more disorganized style, where instead of developing a consistent look, silhouette, or color scheme, you frequently mix things up. During his latest promotional tour for the sci-fi thriller Disclosure Day, Josh O’Connor has displayed traits of a personality dresser, showcasing a variety of styles that fluctuate from preppy to debonair without adhering to a single mood or theme (the common thread being that all outfits are stunning, often designed by Dior). The key point is that while his clothing has reflected various personas—like a millennial dad—they remain consistent with his own style: a scruffy kind of suave curated by stylist Jason Bolden. This notion is also applicable to individuals like Zoë Kravitz, whose casual wardrobe predominantly features The Row, yet she skillfully infuses her personality (or personalities) into those polished, luxurious staples. Dressing in this manner is an art form, one that you can cultivate so that your outfits, while suggesting different personas, consistently reflect you. Scroll down to explore and shop the various personas of three A-listers that might inspire your own style experimentation.

      **Celebrities Defining 'Personality Dressing' in 2026: Josh O'Connor**

      1. **Renaissance Prep**

       - **Style Notes:** Beginning with the Renaissance prepster, historically fond of Polo Ralph Lauren (which is experiencing its own revival) and always sporting boat shoes. The 2026 version, per O'Connor's stylist, Jason Bolden, includes a collar-popped canary yellow shirt by Dior, tailored black trousers, and "fancy" loafers (with a striking buckle, vibrant color, or intricate fabric).

      **Shop the Trend:**

       - Polo Ralph Lauren: Cable Knit Cotton Quarter Zip Jumper

       - JAMIE HALLER: The Essential Cotton and Silk-Blend Shirt

       - Free People: Yachting Day Boat Shoes

      2. **Millennial Dad**

       - **Style Notes:** The "millennial dad" aesthetic, whether or not you’re a parent, has several key elements: retro track pants, functional trainers (like Salomon or Mizuno), and a practical blouson jacket in vivid colors that assert, "I can no longer wear cream." The millennial dad appreciates functional yet stylish accessories: a slogan baseball cap, a branded coffee tote, and a reusable travel mug (often 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 whose personal style is as polished as their presentation skills? That's appealing, and definitely doesn't involve polyester tailoring. O'Connor's take featured custom-made Dior and a Tiffany & Co. archival pin (swoon!), presenting a tuxedo 2.0: a cream jacket paired with a white dress shirt styled with an upturned collar, finished off with a powder-blue tie. Fresh doesn't even begin to describe it.

      **Shop the Trend:**

       - Tiffany & Co.: Elsa Peretti® High Tide Brooch in Sterling Silver

       - With Nothing Underneath: The Dress Shirt: Poplin, White

       - Bustle and Bow: Silk Ribbonette

      **Zoë Kravitz**

      1. **Thrift-Store Hottie**

       - **Style Notes:** Zoë Kravitz’s standard look is often head-to-toe The Row, but she also frequently sports Saint Laurent. This look can be termed "thrift-store hottie": a vintage fur-trimmed cardigan with modern knife-point court heels. It's an easily translatable combination for real life, pairing "cutesy" twinsets with lace slip skirts, stilettos, and curvy oval 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 the allure of Carolyn Bessette Kennedy's minimalist style. This straightforward outfit—a white shirt, black kick-flare trousers, a flowing trench coat, and chisel-toe boots—offers a subtle homage; an everyday ensemble that doesn’t require a tortoiseshell headband to look chic.

      **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 exclusively relies on one