I woulda lost a bet: not ONE of you went for the Austin Powers angle when presented with Richard Simmons in an outfit he stole from my mother in one of her manic periods. But we had some good entries, and now we have a winnah!

Richard Simmons as Austin Powers

Natalie Anne Lanoville
November 12, 2011 at 12:44 am
After putting so much work into his e-Harmony profile, Richard was crushed to find out that Elton John was already married.

Awww, isn’t that always the way: the best ones are either married or gay! Or both! And now for the ceremonial presentation of the imaginary hypothetical prize. In this case, it has to be something just as fabulous as little Richard here, which narrows it down considerably. To second-time champ Natalie we virtually present this swinging Alberto Gozzi Optical Sky Blue Hobo Bag to rock the flower power.

It’s time for a roundup! Next time I remember to tag my posts correctly so I can find them again. A triple-header of captions:

Truly Truman

Salome Valentine
October 7, 2011 at 10:47 pm

I can see clearly now

igirl99 October 28, 2011 at 7:33 pm

Sarah felt a little self-conscious in her budget WallE costume.

Chloe Richardson

Since everyone was struck speechless except iGirl99, and she won the previous one, we’re going to call this Foul, and I’m sure that’s something on which we can all agree.

Now, imaginary prizes for our champs Salome Valentine and iGirl99: First, for Salome, something highly Capoteable: a sterling silver cocktail straw from Tiffany & Co. featuring Capote’s favorite accessory: the monkey on his back.

Tiffany Monkey Cocktail Straw

And for iGirl99, we have the hipster-approved Dr Martens Rafi Saddle Shoe for true rockabilly style:

What is this? I can’t even…

Ladies and gentlemen, “actress” Chloe Sevigny dressed as hipstervert photog Terry Richardson. You know what to do.

Chloe Richardson

Say hello to your new favorite blog: HalloweenOrWilliamsburg!

Morpheus of Williamsburg

“You take the blue pill — the story ends, you wake up in your bed and believe whatever you want to believe. You take the red pill — you stay in Wonderland and I show you how deep the rabbit-hole goes.

What? No, I’m not ‘supposed to be Morpheus.’ I’m trying to sell you ecstasy.”

Just when you thought making fun of hipsters was dead, it springs back to life like the unstoppable killer in a slasher flick, only with less interpersonal engagement. Hours of fun for the whole family, starting with your family right here at the Manolosphere. We’ve scoured the far reaches of that week-old blog to bring you the finest in Caption Contest entertainment, so sharpen your claws and get to work in the comments:

I can see clearly now...that I look like an idiot

After our longest layoff ever, here is the winner of our geekiest caption contest ever:

Alexander McQueen: Paris Fashion Week Ready-to-Wear A/W 09

Natalie Anne Lanoville

August 1, 2011 at 2:50 am 

While Spock grudgingly admired the attempt to depict the Tzenkethi Waveform Anomaly in 3 demensions, he questioned the practicality of the ungainly top-mounted Anti-Matter Flare Dampeners.

In the face of a comment like THAT, what else could I do? We hereby virtually present the 100% imaginary prize of hypothetical awesomenosity: Ponn Farr perfume for Her!

It’s time to get back to blogging around here, so let’s start off with an easy one: Caption Spock here, who is Not Impressed with this uh, remarkable, creation by Alexander McQueen.

Alexander McQueen: Paris Fashion Week Ready-to-Wear A/W 09

You know what to do, so do it in the comments, for fabulous, imaginary prizes!

Tom Cruise longhair

It is time to announce our winner in Friday’s caption contest. Who will it be? Well, it sure won’t be the woman who had to wear the damn thing.

Tennis Ball Dress

igirl99
June 18, 2011 at 5:13 pm

Ballsy!

Congratulations and virtual swag to first-time winner, igirl99. For her hypothetical swag, we virtually offer the imaginary Ettika black leather double wrap tennis bracelet: