Having just returned from a long weekend tip to Chicago, I must say I had pretty positive reactions and was kilted all weekend. Headed out Saturday night in my X-Marks and "Real Men Wear Kilts" black T and I think that helped break the ice a bit. Saw many a folks catch the saying on the shirt, then look down and had a good smile. Was in the X-Marks again on Michigan Ave on Monday and pretty similar. Only negative comments heard were from unknowing/uneducated kids not understanding what a kilt was.
All in all I felt very comfortable in the windy city.
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