If nothing else @MirandaBerman, pay attention to fit. It's a one-way ticket to: DAMN I look good. For the expanded version, see below! I hope this helps?
  1. 1) Fit. Fit. Fit. Fit. Fit. Focus on the fit.
    Everyone has a couple of silhouettes that are (very) flattering. You know: the ones that look good in photos AND make you feel like a million bucks. Focus on these silhouettes because they fit your body best. Also remember: a tailor can work miracles, so if you LOVE something, take it to your tailor and see what they think.
  2. 2) Does it pass the TWO TESTS rule?
    #1: Could you wear it to work, to cocktails, and on the weekend? Okay that's hard, but if you can say YES to two of the, that's good! #2: Can you create three different looks by pairing it with pieces you already own? (Like: with a leather moto jacket & heels//flat boots + tights + jean jacket//sandals + army jacket//different jewelry/belts/bags) Okay fine, TWO ways? That's good!
  3. 3) Is it made from a versatile fabric?
    Lightweight cotton feels very summery and daytime, thick wool is wintery, and some materials can be very "evening," (like most black lace, for example) but there are lots of "seasonless" "all-hours" fabrics that are in between. These are the ones you want for maximum year-round wear.
  4. 4) Does it fit your lifestyle?
    Are you hard on your clothes? Don't buy something super fussy and delicate. Hate the dry cleaner? Look for low-maintenance fabrics or pieces you can wash at home. You're never gonna want to wear something all the time if taking care of it annoys you, so be honest with yourself.
  5. 5) Figure out which brands/designers make things that you like AND fit you well, and then stalk them.
    There is a full-skirted, off-the-shoulder midi dress at ASOS called the Bardot. I love it and now own it in like 7 colors/fabrics. Erdem stretch-twill and cotton-blend dresses fit me really well, so I always seek them out each season. The cuts/fit tends to remain the same/stay similar, which in turn helps me find more dresses I love.
  6. 6) When in doubt, try on lots of things and then walk away.
    If you're still thinking about a dress a day or two later, there's probably a reason. It's like the opposite of buyer's remorse, and usually a sign that you will love said piece and wear it all the time.