Definitely do-able But I do have to say I'm really feeling the guys in grey like the picture that @mimitrue posted
I'm 5'4", sewed a small, and the length is a little long, I may shorten my next one by a couple of inches
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Often, youre seeing your old high school or college friends, or people you might not see all the time, Choi says
I would advise trying several brands in person, with someone else in tow, or at least at a shop with knowledgeable salespeople
If youve never sewn with stretchy fabrics though, this could be a challenge