First off, you should know that I nearly always wear some form of head cover in the winter. Sometimes it's a fedorra for ivy cap, but usually it's a bonnet or beret.
I often wear a TOS (government issue) for knocking around. ACtually, i have several with different badges. I have the older, larger ones and the newer, smaller ones. The look like this:

I also wear a couple of bonnets in blue/black, with red and black toories when I am a little more dressed up. Note: the little bear that appears to be on my bonnet is actually on the mantel behind; looks like a kiddie party, no?


You can see the white cockade on both. I also have a dark green balmoral, but for some reason, I don't opt for it very often.
I sometimes wear a beret for knocking around as well, mostly military styles. I have a carload since I purchased a large lot of ex-military berets quite a while back. I have red ones (which I never wear if someone wants a good buy), a couple of green ones, and a navy blue, all with various badges in place.
You can see me here that the last St. Patrick's parade wearing a green beret with on outdated Royal Irish REgiment badge attached:

I don't wear glengarrys often nor for winter warmth, but I throw in this additional photo just to show that chicks really do go for a man in a kilt.
Jim Killman
Writer, Philosopher, Teacher of English and Math, Soldier of Fortune, Bon Vivant, Heart Transplant Recipient, Knight of St. Andrew (among other knighthoods)
Freedom is not free, but the US Marine Corps will pay most of your share.
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