I think I would be right at home on Glee wearing this little number.
Menswear can look very cool on a woman. I'm partial to fitted vests inspired by menswear. They can be dressy or funky and can help with a larger chest since they act like an outer corset making you look smaller by "locking and loading" your chest (thanks Stacey and Clinton) and defining your waist.
I've taken one of my hubby's lovely silk pocket squares and his Dad's pocket watch for this outfit. The hats are also menswear inspired. In fact the grey poor boy hat is a men's hat that I share with my husband. I liked the outfit better with the bowler hat when I didn't have the jacket on. Hats are an important accessory for me. They leave a lasting impression.
You could definately switch out the jeans for a nice grey or black pencil skirt and switch the boots for some pumps to sex up the outfit.