The Pebble Beach Concours d’Elegance is somehow even more pretentious than its name suggests, with a vibe that’s post-The Fall brought on by original sin but pre-The Fall of Rome (brought on by a whole bunch of sins that were way more original). It’s Hieronymus Bosch with Bugattis and if you go you’ll definitely want to dress the part.

I’ve long contemplated donning a punk rock aesthetic to protest the almost offensive opulence on display, but I’m about as punk rock as a fax machine and if you spend enough time walking around the greens you’ll realize most people are in on the joke. Also, I drove here in a McLaren, so how offended am I, really?


Pebble is perverse in many ways, but perversity can be fun. Embrace it. Own it. Pretend like you drive around in a torpedo-bodied Benz and say nonsensical things like “Hispano-Suiza never made a good car after the Labourdette Skiff!”

Most importantly, though, is to pick the right outfit. Here’s a brief guide to looks you can pull off, ranked from easy to ambitious.

Easy: The Preppy Dandy Or Dandette

Slightly more twee than preppy, with a few accessories you can turn normal clothing you can find at any store into an outfit that suggests you summer in San Tropez and winter in a Whit Stillman movie.


  • HEADWEAR: Panama Hat
  • NECKWEAR: Foppish Bowtie
  • SHIRT: Vineyard Vines or Ben Sherman
  • JACKET: Something in a fun color or with stripes, perhaps seersucker or linen
  • BELT: Something that’ll hold your pants up.
  • PANTS: Stripes, white, or a fun color
  • SHOES: Boat shoes, loafers
  • ACCESSORIES: Pocket square, Alfa Romeo


  • HEADWEAR: Bigass hat with bigass bow or feather/flower
  • NECKWEAR: Pearls
  • DRESS: Conservative, mid-length
  • SHOES: Pumps or strappy sandals
  • ACCESSORIES: Giant Sunglasses, small clutch

Ambitious: The Period Sophisticate

If you’re not content to fit in with everyone else you can attempt to look as though your family never got over the war (in this case, the Second Boer War). Think Downton Abbey without the humor or necessary self-loathing.


  • HEADWEAR: Giant hats with giant scarves
  • NECKWEAR: A locket with a picture of Wilhelmina
  • DRESS: Every inch covered by multiple layers, all the way to the floor
  • SHOES: I can’t see them under your dress but flat
  • ACCESSORIES: A small child in a vintage carriage


  • HEADWEAR: Driving cap and goggles
  • NECKWEAR: Vintage tie as wide as a Packard
  • SHIRT: Saville Row-inspired white
  • JACKET: Long coat or driving leathers
  • BELT: Off a Packard’s supercharger
  • PANTS: If God wanted you to wear long pants why’d he give you those magnificent calves?
  • SHOES: Driving boots
  • ACCESSORIES: Driving gloves, Isotta Fraschini

The only wrong way to dress for Pebble is to not try. Even the smallest effort will make you feel like you belong, which is good, because if you’re like me you definitely do not.

Illustrations by Sam Woolley

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