yes you do. normally you would wear your underwear, then the stockings then the leotard, but if the judges can see your underwear underneath the stockings, eg the line of them or the actual pattern you will lose marks... it's one of those stupid old rules about decency or something...
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yes you wear your under wear with your skating tights over them and your skating dress over your tights (actually - no, most people don't).
the dress wont really make you cold its the skating tights that are cold especialy if yyour standinh
if you are a figure skater, then yes, but only when you compete unless you have a practice dress. at practices just wear a skate skirt, or yoga oants and sweater