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I'm pretty sure that springtime (when it finally arrives), is the best. Also, getting vintage 1940's dresses tailored so that they fit your body and your style, is a pretty close second. Everyone should get things tailored all the time.
I am excited to pick up my wedding dress from the tailor today. I will be getting married in it in less than 3 days (everyone pray for nice weather for me, I think I'm going to need it)!