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Many suit retailers offer tailoring with a purchase, which can be a good way to start. Always test a new or unfamiliar tailor with one suit, so that if he / she doesn't work to your liking; they haven't affected your entire wardrobe!
Once you have your 3 or 4 basic suits, you can slowly add other suits to round out your business and entertaining wardrobe. Remember to keep your suit colors classic, and use what you know about your personal coloring (cool or warm) to choose shades and variations that will suit you best.
The best rule of thumb for Menswear: wear what is comfortable for you, remembering that classic tailoring and the right colors for you will best stand the test of time.
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