For one thing, I wore a slightly wider tie with a woven pattern. I was really digging the whole navy/green/blue/pink combo.
And for shoes and belt, I stuck with a buttery orange shade of brown, and split toes instead of wingtips, with light colored socks. Something about grey flannel and orange leather is very British to me.
Chesterfield topcaot from Andover Shop, $9.99 (swear to God)
Top it all off with a Chesterfield topcoat and a floppy cap in Black Watch Tartan.
Voila! The Ivy League style from before the 3/2, button down collar days. I apologize for the gratuitous amount of photos this post, which include my ugly mug, but I was pretty proud of this outfit, and it kept me warm to boot. If only I had attended Yale in 1928, I might not have had to think so hard about this one as I was getting dressed.
Your feedback on what other contexts I might be able to mask those pleats in would be greatly appreciated, dear readers.