I remember the first time I spent over $100 on a pair of pants. They were black stretch from Barneys and made my butt look great! I remember being so hesitant to pull the trigger, to cross that symbolic spending threshold of ‘you spent WHAT on WHAT??!!’
However, those pants became the go-to for every occasion in which I needed to look good. I finally retired them after many years of wear, dry-cleaning, repairs, folding and unfolding, and the natural neglect a 20 year old assigns to her stuff. They were worth every penny and taught me an invaluable style lesson: when you pay more, you get more.
Very often, spending more money will garner a bigger return in the form of longevity. Since the clothing is made of higher quality materials, constructed with more time and attention spent to detail, it will stay a part of your wardrobe for years, not months, amortizing its cost.
Additional returns on your investment come in the way of better silhouettes, a wider variety of colors, enhanced detailing (buttons, clasps, trims, etc) and more originality. So consider upgrading appropriately. Three $20 Target tops equal one from J.Crew and on up the spectrum until you end with a closet full of beautiful items that although cost in the short run, saved in the long.