Quick map of what’s ahead:
- Why I tried icon looks
- The icons I copied (and the exact gear I wore)
- What fit me, what flopped, and why
- Easy care notes and a few cheap swaps
I spent a year wearing outfits from men’s fashion icons. Not costumes. Real life looks. I wore them to school pick-ups, coffee runs, meetings, and one wedding that ran late and had weird shrimp. You know what? Some looks made me feel brave. Some made me sweat like a hot pretzel. Here’s what happened, piece by piece. If you want a running list of where to track down these pieces (and the affordable dupes), I keep it updated at Sharpman. For an even deeper, photo-packed play-by-play, check out the full road-test report I published on Sharpman.
Steve McQueen: Clean, fast, no fuss
Looking for a deeper dive on how the King of Cool actually dressed? Check out this concise breakdown of Steve McQueen’s style for context.
I chased the McQueen thing with three pieces I actually wore hard:
- Baracuta G9 Harrington Jacket (mine is used, tan, UK 40)
- Persol 714 folding sunglasses (tortoise, polarized)
- Clarks Desert Boots (sand suede, crepe sole)
How it felt
- That G9 fits a little short, which looks sharp with jeans. The collar snaps make me grin. It’s light but blocks wind on cool mornings.
- Persol 714s fold into my pocket. Wildly handy. They’re weighty but don’t pinch my nose.
- Desert boots are comfy out of the box. But in rain? The crepe sole slides like a dog on tile.
Wins
- Timeless. Easy. I could meet a client or my kid’s teacher and not feel loud.
Gripes
- G9 needs a sweater under it once temps drop. Dry cleaning is a thing.
- Desert boots stain fast. I sprayed mine with suede protector, which helped a bit.
Sizing tip
- My jacket: true to size. Desert boots: I go down half a size. Persol: medium fit; I have a round face and they balance well.
James Dean: White tee, jeans, leather—simple and bold
For a playbook on getting that rebel look just right, this primer on James Dean’s style lays out the key moves.
My kit:
- Hanes Beefy-T (white, size M) and Uniqlo U Crew Neck (white, size M)
- Levi’s 501 (rigid, 32×30)
- Schott Perfecto 618 (black, size 38)
How it felt
- The first time I wore the Schott, I stood taller. It’s heavy, like a hug with zippers.
- The Uniqlo tee has a cleaner neck and thicker cotton. Hanes is softer but can show a bit.
Wins
- The 501 rise sits right. The leg has a clean line. Roll the hem and you’re done.
Gripes
- The leather gets hot indoors. I took it off at a dinner and felt like I shed armor.
- 501 rigid denim is stiff for a week. I wore mine damp around the house. I wore mine damp around the house. It helped.
Fit notes
- If you’re bigger up top, the Perfecto can feel tight in the shoulders. Size up one.
David Beckham: Sporty luxe with a street touch
My mix:
- Adidas Samba OG (black/white)
- J.Crew wool topcoat (Crosby fit, navy, 38R)
- Plain beanie (charcoal)
How it felt
- Sambas are low and quick. Great for walking my dog and getting a flat white.
- The topcoat over a hoodie feels like a cheat code. Warm. Polished. Not too stiff.
Wins
- I felt put-together but not try-hard.
Gripes
- Sambas are narrow. My pinky toe had comments on day one. Broke in by day three.
- The coat collects lint. I carry a small roller in my glovebox now.
Pharrell: Color, play, and a wink
What I wore:
- Bright varsity jacket (green, thrifted)
- Pearl strand from Miansai (short, subtle)
- Loose shorts with white socks and loafers (G.H. Bass Weejuns)
How it felt
- Fun. Like I let the kid in me out for air.
- Pearls with a sweatshirt? People smiled at me. That was nice.
Wins
- Low effort, high mood. Great for weekend markets.
Gripes
- In a quiet office, it felt loud. I kept the pearls and swapped the jacket for navy.
Harry Styles: Soft shirts, drama pants
My spin:
- Satin shirt from Zara (cream, flowy)
- High waist trousers (slight flare, H&M, black)
- Nail polish (clear; tiny flex)
How it felt
- Date-night gold. The fabric moved when I walked, which felt… fun.
- The flare gave my shoes more stage time.
Wins
- Photos looked great. My partner said “Oh hello.”
Gripes
- Satin holds sweat marks. I layered a thin tank under it. Helped a lot.
- Wrinkles fast. Steam it, don’t iron hot.
One week, I pivoted hard into darker territory and trialed a full gothic capsule; you can see what survived the purge in this breakdown.
Tyler, the Creator: Preppy with a curveball
My picks:
- Pastel cardigan (lavender, Uniqlo)
- G.H. Bass Weejuns (wine, leather)
- White socks, cropped chinos
How it felt
- Cozy and neat. Like a school uniform, but cooler.
Wins
- The color lit up my skin. People notice in the kind way.
Gripes
- Weejuns run stiff. Blisters day one. I used thick socks and a bit of moleskin on my heel. Day four felt fine.
Jeff Goldblum: Smart, odd, and sharp
My go-tos:
- Black acetate frames (Warby Parker, square)
- Patterned camp shirts (Noah, thrift finds)
- Dr. Martens 1461 (black, smooth)
How it felt
- The 1461s are tanks. Good weight. Look better beat up.
Wins
- Camp shirts let air flow. Great for hot days with a blazer tossed over your shoulder.
Gripes
- Doc break-in is real. I wore them to the grocery store only, for a week. Then they became friends.
Timothée Chalamet: Slim, crisp, a touch of fancy
What I wore:
- Cropped suede trucker (brown, Levi’s Made & Crafted, used)
- Slim trousers (no break)
- “Tank” style watch (Seiko SUP880, gold-tone)
How it felt
- Light and sharp. The small watch face felt classy, not flashy.
Wins
- Great for a quiet dinner. Photo-ready without effort.
Gripes
- The short jacket needs a high rise pant. Low-rise looked off on me.
Idris Elba: Cool-tailored, strong without shouting
My set:
- Knit polo (Sunspel Riviera in navy; I also tried Uniqlo’s Airism knit)
- Chelsea boots (Thursday Boot Co. Cavalier, black)
- Dark sport coat (unstructured)
How it felt
- Easy power. I stood in a coffee line and felt calm.
Wins
- Knit polos breathe. No stiff collar fight.
Gripes
- Chelsea boots need a solid pant hem. Too short and they look clownish. I aim for a slight break.
The Meme Uncle: The Rock’s black turtleneck
My fun test:
- Black merino turtleneck (Uniqlo, M)
- Silver chain (thin)
- Old leather belt bag (yes, fine, fanny pack)
How it felt
- Cozy. A little silly. Also kind of cool?
Wins
- Warm, sleek, good for a cold movie night.
Gripes
- Lint magnet. Carry tape or a brush.
What Stayed In My Closet (and What Didn’t)
Kept and worn weekly
- Baracuta G9
- Levi’s 501
- Knit polos
- G.H. Bass Weejuns
- Persol 714
Kept for nights out
- Schott Perfecto 618
- Slim trousers with no break
- Seiko “tank” style watch
Rehomed or rare
- Satin shirt (too fussy)
- Desert boots (rain fail city)
- Loud varsity jacket (great mood, hard to match weekdays)
Fit Tips I Wish I Heard Sooner
- Shorter jacket + higher waist pant = clean line. If the jacket is cropped, raise the rise.
- If shoes chew your heels, thick socks for three short wears. Then switch to thin.
- Narrow sneakers? Pull the insole and try them indoors for five minutes. If your toes still pinch, size up half.
Care Notes That Saved Me Money
- Wool topcoat: hang after wear, brush with a horsehair brush. Lint roll before you walk out, not after.
- Leather jacket: small dab of conditioner