Gym Clothes

Save or Spend? Spend.
Experts Say: The great thing about gym clothes: Even if you choose to buy the best (instead of sweating in a ratty old T-shirt), you won't burn a hole in your wallet. Gym clothes aren't that expensive, and the pieces will most likely last for years to come. "Invest in something functional," advises Brumbaugh. Be sure that the outfit feels flattering. "When you look good in your workout clothes," says Brumbaugh, "you're more inclined to work out." But don't overdo it: A great pair of pants and a couple of tops will do the trick. (Supplement them with those college tees.)

Trendy Items

Save or Spend? Save.
Experts Say: With all the discount retailers out there, you can avoid overspending on fashions that will feel passé after one season. These stores offer trendy items at fair prices, says Los Angeles–based celebrity stylist and designer Phillip Bloch. But remember: Some trends, like nautical-inspired clothing and tunics, will come around again and again, so go ahead and splurge on an item you feel has staying power.

Black Pants

Save or Spend? Spend.
Experts Say: A high-quality pair of black pants can last for years. "Black pants are timeless," says Andre. "And investing in a good pair is smart, as the wear and tear on them is typically greater than on most wardrobe items." Farr agrees: "Spend more on at least one pair of well-tailored tropical-wool black pants." Better fit and craftsmanship and higher-quality materials cost a bit more, but you'll save in the long run, as you won't be spending twice as much buying a new, cheaper pair every year.

Jacket

Save or Spend? Spend.
Experts Say: "A very good jacket can do a lot for your overall look," says Brumbaugh. "You could wear just a T-shirt and jeans, but an expensive, fabulous jacket upgrades your outfit." Look for a jacket to fit the widest part of your body. If you have a large bust and a small waist, buy a jacket in a size that will close over your bust. Then go to a reputable tailor and have the jacket taken in to fit elsewhere.