@The Noodles, you want to buy the boring stuff first so that you have it when you need it and can then buy things that are a bit more fun once you have a well rounded wardrobe. As others have said, a bunch of one off pieces you happened to like does not a complete wardrobe make. JRD has good advice about buying a tape measure so that you can actually compare different garments in a more scientific manner. Glad you're finally posting fit pictures with shirts that are tucked in, though. Also, before you buy various fun sport coats, do you own a basic navy blazer?