Do Cowboy Boots Go With Martinis?! What To Wear To A Gutsy Affair?

Boys and girls, by now (I friggin’ hope) you know about A Gutsy Affair this Thursday night at Revival.

This open Martini bar event is being held to support the Crohn’s and Colitis Foundation of Canada and is being billed as “the event” for Toronto’s young professionals. And it has become one of the hottest tickets in Toronto so far in 2011.

The question now, 2 days before the party is this: What do you wear to an open Martini bar fundraiser with the biggest and brightest in Toronto?

First of all, let’s get the disclaimer out of the way. I am not a fashionista (fashionisto?) my friends. I am just a dude who picks clothes up and puts them on in the hopes that people don’t point and laugh. With that said, I am here to pass on some of the knowledge that I’ve overheard on the internet in the last few days.

A Gutsy Affair is going to be a dance party with live tunes from The Pigott Brothers and DJ Agile. So you’re going to want to rock something comfortable enough to bust a move in. That means you’re going to want to wear your dancing shoes kids! It also means that I’m not wearing my 6 inch spiked heels. Sorry.

Instead I’m toying with the idea of wearing my beautiful brown cowboy boots. That’s right, the country boy drinks martinis. Because we’re only Tuesday now and the party is Thursday night I have a whole day in the middle to polish them up for the first time this Spring.

What goes with the boots though? I’m thinking some hot jeans by Denver Hayes (Marks Work Warehouse baby!) to keep the country feel alive in the oufit. I know that everyone thinks Wranglers and Brett Favre and George Strait are cowboy jeans. But let’s keep things Canadian shall we.

Up top there are a few options. Because we’re starting to get some warmth in the air I’m seriously considering my vintage (read: was my step-dad’s) navy blue pin striped blazer. Under that I’m still debating. We could go shirt and tie. It seems like a good way to class things up just a little bit. The other option is of course the simple t-shirt look that usually works quite well. I’m leaning towards the shirt and tie – but I’m looking for your thoughts here mes amis.

And remember – we’re fighting a disease that currently has no cure, so donations are encouraged even if you can’t make it to Revival to have a drink with me. Please visit the A Gutsy Affair website right now to learn more and help.

That would make you Awesome!

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Joshua Murray

creator of content, daddy blogger, writer, coffee drinker, fan of the Batman. proud mo bro. prouder dad.