Ascots are so damned hard to wear. I have a few, but I hardly ever wear them. Truth is, they are the very height of pretension in America in the times in which we live. Wear one with a suit, you're a chump. Wear one with a blazer, you're pushing it. But I like them (I think) so I keep trying. Maybe the answer lies in comfortable casual.
With s striped button down and cotton crew neck sweater, you'd hardly even know it was there, would ya?
Brought down further with dark denim, grey socks and brown shoes. Though it may be to the chagrin of many of you, I think it's time to admit that brown dress shoe/grey sock/dark denim as a combination has reached full "classic" status.
As a side note: those $20 Wranglers that I wash all the time are looking pretty stylish...and they don't have a years worth of filth on them, nor did they cost hundreds of dollars. Imagine that?
So anyway, if you're going to wear an ascot, do yourself a favor and minimize the pretension by keeping it casual. Do yourself an even bigger favor and eliminate the pretension by not even wearing the damned things. Ascots are useless and obnoxious.
But I do like to wear one, from time to time...
