In the last 6 months I've mustered up the courage to incorporate the ascot into my repertoire. For someone that has crossed that fine line into "costume" so many time in my past, the ascot was daunting to me, but a few attributes made it an essential addition to my wardrobe.
An ascot commands attention. Fabric leaping from the chest of the wearer says, "I'm making a sartorial choice that most won't, and for that reason, you should listen to what I have to say, for I am obviously confident and unpredictable".
I have a bigger frame than a lot of guys, but like a slimmer fitting shirt, so rarely does a shirt collar fit around my neck unless I've had a larger shirt tailored to fit me. The ascot allows me the opportunity to buy some smaller shirts that fit my torso perfectly with a few buttons undone, and still accessorize it.
An ascot can invoke several different era's of fashion and can add a level of playfulness that you can't get with a tie. I find myself in a rut sometimes, with my suit, vest and ties, the ascot breaks me out of that rut immediately.
Chuck Bass wears ascots. That's usually reason enough to wear something.
Right now I own 3 ascots, and they honestly don't get as much attention as the bow ties do, and I think it's because they don't clash as much as a bow tie, they are fluid. Unless you have drastically contrasting colors, they are purely an enhancing accessory. With the exception of the Timberlake pic, in which he is wearing black against all light colors, and the Colin Farrell pic, where, he is wearing the ascot more like a loose tie, the ascot is...well...just there. But it's that nonchalance that can have it be fancy and casual at the same time.
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