An important part of building a wardrobe is building a "capsule wardrobe." The idea is to have the minimum amount of pieces that create the maximum amount of outfits. What items you use are entirely dependent on your style, but looking through MFA and even Pinterest can help you develop what you're looking for. It will help simplify your clothing hunt and once you've built a foundation, make it easier to keep up and cycle through over the years. As well, a good tailor is your best friend. It doesn't matter a lick how expensive a shirt is if it doesn't fit you properly, and fit makes a WORLD of difference. Here's a good place to start. Finally, I always ask myself, "Do I actually see myself wearing this?" Far too many people buy clothes because that's what they think they need or because it looks "okay." Love what you're wearing and you will put far more value into what you pay and the upkeep. Clothes will do nothing for you if you don't have confidence in them, and you'll save yourself a lot of money if you don't buy things you'll only wear once and then leave in the bottom of the closet.