you'd look sweet upon the seat of a bicycle built for two
November 6, 2009 12:57 PM   Subscribe

My boyfriend and I really want to win Most Stylish Couple at The Sadie Hawkins Style Ride in one week. Any suggestions? (previously)

There is no way on earth we are winning Fastest Couple; normally I wouldn’t even participate in a ride since I’m the speed-racing equivalent of a child riding on the sidewalk or a pedicab, but it’s a short ride (~3 miles), you can skip checkpoints and hop to the bar if you’re not concerned with winning Fastest Couple, the money goes to a good cause, there’s beer at the end, and I really want that pair of Seagull Bags.

I have a teal&orange little boy’s bike from the late sixties or early seventies; it’s a Schwinn Stingray knockoff. My boyfriend has a yellow Schwinn Varsity.

So, how do we dress? I’m a girl with most of my somewhat eccentric wardrobe obsessively cataloged online, if you know where to look for it. My boyfriend’s most distinctive features are a blonde handlebar mustache and a collection of brightly colored skinny jeans. We’re riding at night in Chicago’s November, so all-black clothing is probably not genius, and moderate warmth is a must (it’s not snowing or anything and I generally heat up on my bike, but it’s definitely tights&hoodie weather).

The best idea I’ve had is my boyfriend dressing like an olde timey admiral with a captain’s hat and me dressing like a pirate with a pirate’s hat,with my eyepatched sock monkey riding in my jolly-roger-outfitted bike basket. This really isn’t that costumey for us (I’ve worn both those hats to shows and he wears that captain’s hat everyday to work) but given the timing I worry it’ll look like we just reused our Halloween costumes.

I have access to two bright and colorful wardrobes, a million accessories including a backpack shaped like an owl and a sombrero, and pretty much every store in Chicago proper including craft stores and a bunch of resale shops in Boy’s Town. So, what other themes could we go for to look like a super-stylish matched cycling couple?
posted by Juliet Banana to Clothing, Beauty, & Fashion (9 answers total)
You could go hard on the "stylish" aspect, ala matching ruffled pastel-colored suits and top hats like in Dumb & Dumber. Or tuxes. Or old-timey tuxes. If I were judging at the checkpoints, stylish =/= wacky. A throwback to a 70's Sadie Hawkins Dance might also be appropriate.
posted by craven_morhead at 1:12 PM on November 6, 2009

You might want to consider a different bike. An adult on a child's bike is going to appear more NAMBLA than stylish, especially if you appear with a grown man with a big mustache.

Something that would get everyone's attention is if you guys did something really simple and stark, like showing up completely white. White hair, white bodysuits, white capes, white face paint, white bikes. You'd look like white blurs in the night.
posted by ignignokt at 1:17 PM on November 6, 2009 [2 favorites]

This seems like as good a time as any to go full steampunk.
posted by oinopaponton at 1:24 PM on November 6, 2009

(since full skirts sound terrible for biking, you'd probably want to do steampunk with bloomers. Biking is what bloomers were made for, anyway)
posted by oinopaponton at 1:29 PM on November 6, 2009

Yeah, "handlebar mustache" screams out for a steampunky thing.
posted by Sidhedevil at 1:36 PM on November 6, 2009

You really need to do this and there is still time! As a tandem captain and matching outfit guy I say here is permission to go all non-matching, let him look like a tweed ride guy.
posted by fixedgear at 1:43 PM on November 6, 2009

You need to be steampunk AND you need to have CRAZY banners for out-of-date political parties and movements.

"TEMPERANCE FOR TREES!" or some such. Go as a Lady Suffigette and a bomb-throwing anarchist.
posted by The Whelk at 4:21 PM on November 6, 2009 [1 favorite]

The Captain and Tenille?
posted by benzenedream at 6:09 PM on November 7, 2009

One more: An old-timey B&W villain (with monocle and waxed moustache) and a damsel tied to the railroad tracks? Not sure how you could rig the railroad tracks so as to be bike-friendly.
posted by benzenedream at 6:13 PM on November 7, 2009

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