I found when I first started wearing a kilt that the thing that got me the most comfortable with it was wearing it to the mall. Basically any semi-anonymous space where there are people but you don't know them. I will note that I wear kilts very casually, so I'm not too far outside of normal attire in a space like this. You learn very quickly that while a kilt does draw attention, there are an awful lot of other guys out there who have a kilt and never wear it. And if you don't run into one of those, you'll hear from girlfriends/wives/etc. who want their significant other to wear a kilt but don't know how to get him to. You get the occasional joke - just have a few witty responses planned for stuff like "nice skirt" (see other threads on the forum for some great and hilarious stock responses) or "you wearing underwear?", but these are less common than people who either own or are genuinely interested in kilts. The great thing about a semi-anonymous place is that you can get comfortable with it around total strangers who you never have to worry about seeing again. And if you feel like you're giving off a bad first impression and you think you need to change something, it's not like you're out much.
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