Last Thursday I threw a party. There was fashion, there were walk-offs, and there were prizes. If you make it to the end of this entry, you can enter to win a prize of your own.

Here’s how it started: several weeks ago I blogged about getting picked for a Brand Enthusiast program for the Gap. Part of being a Brand Enthusiast is reintroducing my friends back to the Gap, specifically the new 1969 denim line for men & for women.

Here’s how that was supposed to work: The Gap was going to send me a bunch of denim and some party supplies to have an in-home party where my guests could check out and try on the jeans.

You know me. I don’t do anything the easy way. And, as an event planner, I like to have events. In-home party? Easy, but not an event. So I called up a few people, told them what I was doing and threw out some ideas, and a couple of hours worth of calls, emails and meetings later, I secured a venue (Thanks 28 Degrees Boston!), got donated food (Thanks Carl!), and sponsored goodie bag items (Thanks Van Gogh Vodka!).

I had to design the guest list and design the event (create and print signage, sketch out the layout of the lounge and come up with activities). Done. Done. Annnnnd done.

Here’s how it all went down: First the set up. The lounge space that was donated was simply gorgeous and needed no help. I just had to set up the jeans.

Clearly after setting up the jeans we had to pose with the signage.

Before the party I had prepared a … presentation … that was to be projected on the large screen on the whole back wall of the lounge and loop for the duration of the party. It talked about the sponsors, and me and … well. How about you just watch?

Click the screenshot to run the presentation. It’s worth it. Bonus points if you “get” the pics …

My guests arrived and mingled. I explained to them the event: Come try on jeans! Enter to win a raffle! Tweet about the party! Sign up for …. THE AMERICA’S NEXT TOP MODEL STYLE FASHION CHALLENGE (oh yeah, you just wait.)

After a couple of hours, everyone had found their fit. And if we’re in full disclosure mode, I feel as if I should disclose this: I have a lot of gay friends. A lot of gay friends who like, apparently, to wear women’s jeans. Honestly? I think more than 50% of the men invited took home women’s jeans. And I had three women take home men’s jeans.

WE BREAK ALL THE MOLDS OVER HERE IN ALL EYES ON JENNY LAND

Then it was time for my FASHION CHALLENGE. Now that everyone had found their pair of jeans, I got a group of runway divas to model them for us. But of course, there’s more to it than that.

I cleared the remaining party guests into a runway path, and sent the contestants up into the fitting room behind the curtain to get ready. I had pre-selected three bitchy but hot judges, and gave them numbers to score each contestant.

You that’s Sarah right there in the middle!

And, of course, I got to be Tyra.

I had purchased a WHOLE LOTTA accessories for this challenge, dumped the accessories on the floor in the middle of all the contestants and gave them their challenge: they had ONE MINUTE to grab whatever accessories they could get their hands on and accessorize the hell out of their new jeans. They would then walk the runway and get JUDGED.

Oh. Hells. Yeah.

In the end two contestants tied. And we had to have a walk off. They wished each other well and gave it their all.

My friend Mike won, and Sarah took the news like a champ and threw her wig on the floor and stormed off.

Mike won a digital camera and Sarah won a $50 gift certificate to the Gap. Good work kids ;)

All in all, the party was a BLAST. We all had SO much fun. And got some awesome new jeans to boot.

Thanks again to …

The venue: 28 Degrees
The goodie bag and prize sponsor: Van Gogh Vodka
and of course
The clothing sponsor: THE GAP!

Check out the whole set of photos here. (There is video to come, but I had over 2 hours worth and it took me a whole weekend just to get through the photographs!)

Congratulations. You made it to the end! You should be rewarded by entering to win my contest!

The Gap was kind enough to give me an extra $50 gift certificate to give out to a reader on my blog! Here’s how you enter to win:

1.) Comment on this blog post to be entered into the contest once!
2.) Twitter linking to this post and using the #GapBornToFit hashtag to be entered twice (don’t forget to get an ‘@alleyesonjenny‘ in there so I can keep track of you! May I suggest something like “Visit the blog of @alleyesonjenny and enter to win a $50 gift certificate to the GAP! http://tinyurl.com/o6dv9g #GapBornToFit“)

You have until 10 pm on Tuesday, August 18th to enter. The winner will be chosen at random and announced Wednesday morning!

Good luck!