Get Things Tailored
Been hitting the gym and now your old buttondowns and chinos don't fit anymore? Take 'em to the tailor. If you're buying quality pants, any tailor should be able to take them in or let them out. Fits and styles change constantly, and it will be easier on your wallet if you don't replace everything in your closet every season. Not to mention, clothes that fit you well now won't fit well on you +/- 20 pounds. After all, Thanksgiving is just a few months away.