Well, if nothing else, the concepts of “traditional” and “conservative” are applicable to the horseshoe.
I might offer the advice to figure out what your bald clients do to keep their heads warm. After all, they’re the membership of the club you’re looking to join.
Absolutely don’t wear any kind of classic or formal hat.
Personally I would wear a beanie with a suit (outdoors and during cold weather, preferably with overcoat).
I say try a beret. Classic, with a hint of artsy chic.
Plus, when you’re telling all the chicks about your Special Forces days…
Seriously, tho, a beret will serve you well.
Best wishes,
hh
I wear on occasion fedoras, straw hats, Western style hats, Australian style hats, and berets. They all have their benefits and I love them all.
I can say with confidence that the OP does not want to wear a beret.
No, the beret is a bad idea. In all seriousness: my vote is with the flat cap/driving cap/golf cap/gatsby cap/newsboy cap/Great Depression cap/whatever the hell else you want to call it. This is definitely the best hat if you’re seeking to both be dressy/classy and also unobtrusive. A solid-color one would go well with a dark suit and coat. It hasn’t been appropriated by hipsters yet, so it doesn’t have the same “look-at-me” vibe as the fedoras, trilbys and other brimmed hats like that. Old guys at my Masonic Lodge wear flat caps (accompanying formal dress and overcoats) without any ostentatiousness whatsoever.
ETA: the key with this type of hat is that it has to fit properly. One that’s too big will look goofy and floppy.
You could let your hair grow.
You could read the thread.
An important part of wearing a hat with a suit is getting a good hat, something like a Borsalino or Christy’s.
With your bald look and your self-consciousness, I suggest something like this: Borsalino 8/4 Style Wool/Cashmere Cap - Black.
Cold climate lady Doper here.
My take is that, when it’s cold out, nothing that you wear outdoors to keep you warm counts against you until after you have come indoors and had a few minutes to prepare to present yourself.
So I’d go with the (easily squashable) knit hat, taken off (stash it in the briefcase or something) as soon as you are indoors.
Then hipsters would stop wearing hats and start wearing cummerbunds or spats, just to stay ahead of the curve.
