I Road-Tested Men’s Fashion Icons: What Actually Works On A Real Body

Posted bysarymervyn

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