I just lost like 100 lbs and now all of my shirts are huge on me. Should I get them tailored or buy new ones?
You should probably buy new ones, for three big reasons:
First off, tailoring huge shirts helps shirts fit, but it does not fix all aesthetic problems. Big shirts tend to be proportionally big, meaning that in some cases the pocket, collar, and sleeves can be bigger in a way that cannot be easily (or feasibly/cheaply) tailored.
Second off, chances are if you have older shirts they will be a little bit worn anyway. In many cases, tailoring older shirts is a waste of time, as the shirts are falling apart, and the cost you put into making them fit is disproportionate to their current worth.
Third off, tailoring is really only economical with fairly used shirts when those shirts are fairly expensive, i.e. over $50-60. While you should get any shirt that you purchase tailored, poorly fitting used shirts are usually best replaced unless they are worth much more than the cost of tailoring. Given that extensive tailoring can cost $10-20, a shirt worthy of tailoring generally needs to be worth more than $50.
So basically, the answer is simple: unless you have a few Brooks or Armani shirts that you had when you were larger, just buy new shirts. Consider it a reward for your weight loss.
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