Hat fashion is really the slowest-evolving and least experimental limb on the ever-changing style tree.(Mixed metaphor or what?) I get it though–BOY, DO I GET IT. In my mind, hats are like cigarettes that will probably never kill you: wear them right and you are balls deep in je ne sais quoi from je ne sais quere! Wear them wrong, though, and it is nothing but misery and awkward fumbling with that cross-body bag for you, mister.
As someone who has been there and done that, I can say it is mainly about practice with hats. It has taken me years to become the competent hat-wearer I am known
in elite circles, only to be spoken about in reverent, hushed tones to be today. Strap in for tips!
The bane of any brimmed-hat-wearer’s existence. It is in times like these that I turn to the only person who can help, Diane Keaton. According to this one photo I once saw of D-Keats, it is proper to remove said brimmed-head-kite-from-hell and carry it. *The preferred method is to perch it atop one hand, outstretched at shoulder height as if a short, invisible friend is wearing it.
Option 2 involves Elmer’s glue…
SWEATSHIRTS AND/OR BAGS
Yeah just take off the hat for a sec. This move will get cooler over time, when you get real one-two about it!
The best way to handle a mouth handshake in a hat is to remember that the other person has purportedly seen you in the hat and is still up for the adventure, so the pressure’s off! (If they can’t see the hat, just yell out, “I AM WEARING A HAT.”) Go in for the kill with the confidence that has likely been imbued by the hat in question and if it falls off in the process, look at it as a test of the kisser’s affections; if they don’t chase after your precious head-topper are they really worth your saliva?
This is the scientific term for what happens when your hat is too g-dang big and it sinks down over your eyebrows until you look positively turtleicious. So far the only solution I have come up with it to wear a sturdy pair of sunglasses and not take them off for the entirety of your hat time. It’ll be ok, I bet.
As to a more experimental venture in hat fashion, what about wearing old-timey Jackie-O hats with jeans and a t-shirt? HMMM?! (No seriously, I’ll wait for an opinion.)