Wearing a uniform and sticking to it is the high-step-count, asleep-by-9.30-pm version of you. Personality dressing, on the other hand, involves a slightly more chaotic approach, one where, instead of cultivating a definitive look, silhouette or colour palette, you keep changing things up.
On his recent promo tour for sci-fi thriller Disclosure Day, Josh O’Connor has been exhibiting all the signs of a personality dresser, emerging in a stream of looks that, instead of subscribing to a single mood or theme, identify as preppy one minute and debonair the next (the unifying factors are that all the looks are fabulous and often designed by Dior). The crucial takeaway, however, is that whilst his outfits have evoked several characters—millennial dad, for example—they’ve stayed true to his personal style: a scruffy kind of suave, masterminded by stylist Jason Bolden.
This is also true of someone like Zoë Kravitz, whose off-duty wardrobe is usually The Row, but who manages to bring her own personality (or personalities) to bear on those very polished, very rich basics. Dressing like this is an art, but one you can nurture so that your clothes, whilst hinting at different personalities, always look like you. Keep scrolling to see and shop the various personas of three A-listers that can inspire your own experimentation.
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Celebrities Defining ‘Personality Dressing’ in 2026: Josh O’Connor
(Image credit: Who What Wear UK)
1. Renaissance Prep
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Style Notes: Kicking off with the Renaissance prepster, someone who used to be partial to Polo Ralph Lauren (which, by the way, is very much having its own renaissance) and was never not wearing boat shoes. The 2026 version, according to O’Connor’s stylist, Jason Bolden? A collar-popped shirt in canary yellow by Dior, pressed black trousers and “fancy” loafers (a statement buckle, jazzy shade or elaborate 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
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Style Notes: The “millennial dad” look—whether or not you’re actually a parent—has several tenets: retro tracksuit bottoms, technical trainers (Salomon or Mizuno) and, last but not least, a practical blouson jacket, all in the kind of saturated hues that say, “I can no longer wear cream”. The millennial dad also loves functional accessories with fashion credentials: a slogan baseball cap, a branded coffee-shop tote bag and a reusable travel mug (usually 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
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Style Notes: A CEO with personal style as smooth as their presentation skills? That’s hot, and most definitely does not include polyester tailoring. OConnor’s take was custom-made Dior, plus an archival pin by Tiffany & Co (swoon!), which translated as the tuxedo 2.0: a cream jacket and a white dress shirt with its collar upturned, finished with a powder-blue tie at the base of the throat. Fresh doesn’t even begin to cover 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
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1. Thrift-Store Hottie
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Style Notes: Zoë Kravitz’s default setting is head-to-toe The Row. Right? Kind of, because sometimes she does a brisk trade in Saint Laurent. I like to call this particular look “thrift-store hottie”: a vintage fur-trimmed cardigan with new-season knife-point court heels. It’s a combination that you can easily translate into real life, mixing “cutesy” twinsets with lace slip skirts, stilettos and curvaceous 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
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Style Notes: Even Kravitz isn’t immune to the draw of Carolyn Bessette Kennedy’s brand of minimalism. This simple outfit: a white shirt, black, kick-flare trousers, a fluid trench coat and chisel-toe boots, is as subtle a homage as it gets; an everyday look that doesn’t need a hard tortoiseshell headband to look on point.
Shop the Trend:
M&S
Pure Cotton Girlfriend Shirt
Ninetypercent
Kick Flare Pants
Khaite
Nevada Leather Ankle Boots
3. Final Boss
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Style Notes: The actor-director relies on one label and one label only for after-dark dressing: Saint Laurent. Glam but grounded, this tonal brown look features a second-skin turtleneck, high-waisted, pleat-front trousers and flat shoes (all the better for putting your foot down when it matters the most).
Shop the Trend:
Saint Laurent
Turtleneck Top in Stretch Jersey
The White Company
Fluid Trousers With Darted Cuff
Le Monde Béryl
Stella Slipper
Naomi Ackie
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1. Dressy Surfer
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Style Notes: Bermuda shorts and pointed-toe slingbacks? That’s already veering into dressy-surfer-girl territory. Naomi Ackie took it one step further, however, mixing in primary-colour knitwear, wrap-around shield-style shades (perfect for catching waves and commuting alike) and, last but not least, the bag everyone wants to carry and be seen carrying: Loewe’s Amazona 180.
Shop the Trend
MATTEAU
Pleated Organic Cotton-Blend Twill Shorts
JIL SANDER
Ribbed-Knit Wool Sweater
2. FTSE Fashionista
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Style Notes: Here we have an FT-subscriber who also knows how to work a whip-smart pencil skirt. This polished—and provocative—two-piece by Schiaparelli creates an after-hours persona easily tapped into with suiting that’s sculpted to perfection and a pair of ladylike pumps.
Shop the Trend:
Schiaparelli
Oversized Pleated Pants
Anonymous Copenhagen
Trini 40 Stiletto Shiny Lamb Black
3. Prada Architect
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Style Notes: The Prada architect is a way of dressing that says, “I designed this year’s Serpentine Pavilion.” Ackie’s look is actually Prada—a salmon button-down, tangerine bloomer shorts and a sheer, drop-waist pinafore—but you could mimic its mood with grandad-collar shirts, tapered-fit trousers and flat, square-toe sandals.
Levi Strauss & Co.
Elaine Utility Lightweight Shirt
Prada
Cigaline midi-skirt with suspender straps
