Wool Flat Cap... a no-no with a kilt?

[Lime]

Maybe it's because I grew up in the city, but I really can't remember ever seeing a young or even middle aged guy wearing one.
I'll have to keep an eye out next time I'm home and driving through some culchie areas.

I asked my wife about this last night and she rolled her eyes and gave me to understand that "yes... I really am that bad"!

I think it is a combination of being "follically challenged", a spectacles wearer (I really don't have that much going for me do i?) and living somewhere where there is plenty of rain and wind so the old flat cap has become a trusty friend. Oddly enough I've never thought about wearing it with the kilt; I have a sort of fore and aft foldable tweed hat (I don't know what the technical term is) and a balmoral... which is warm and comfortable but not very good at keeping rain of the specs.

[LitTrog]

I think it is a combination of being "follically challenged", a spectacles wearer (I really don't have that much going for me do i?)

Hey, I think your description sounds quite fetching, if only because I'm close to that as well. My hairline seems quite frightened of my eyebrows--it's been backing away slowly for years, and I finally realized that a Clint Eastwood-style squint only looks good on Clint Eastwood. Makes me look constipated.

Daily flatcap wearer here, too. Great for driving to work.

[Peter Crowe]

I asked my wife about this last night and she rolled her eyes and gave me to understand that "yes... I really am that bad"!

I think it is a combination of being "follically challenged", a spectacles wearer (I really don't have that much going for me do i?) and living somewhere where there is plenty of rain and wind so the old flat cap has become a trusty friend. Oddly enough I've never thought about wearing it with the kilt; I have a sort of fore and aft foldable tweed hat (I don't know what the technical term is) and a balmoral... which is warm and comfortable but not very good at keeping rain of the specs.

My wife doesn't mind me in a flat cap, but otherwise what you say is also true of me (receding hairline and glasses). Generally I prefer to be bare-headed, but in damp or cold weather I wear a flat cap in the cooler months of the year because I really dislike wearing baseball caps, and that is a hang up from living in Glasgow and never wanting to look like a Ned.

Like you I never wear a flat cap with the kilt. A balmoral yes, a deer-stalker perhaps, and a tilley style sun hat in the heat of summer, but not a flat-cap.