First off, if you have lots of tall relatives, but you aren't very tall yet, then you will probably outgrow clothing in a few years. For instance, don't expect to be wearing that $400 pair of oxfords five years from now-even though a good, gently treated pair will still be in good shape by that time. The same goes with clothing, and especially suits. If you buy a high-quality, full-canvassed suit right now that is a size too big, you might be thanking yourself a couple of years down the road once you've grown a little more. But, on the other hand, if you buy expensive and high-quality clothing that is a little large right now (hoping to grow into your wardrobe), but then your fashion tastes change before you grow very much, you will end up getting rid of clothing that never actually fit well; in other words, your economy in purchasing too-large clothing will have been completely pointless. When I was 16, I bought a tux shirt that had too-long sleeves, so that I could grow into it. It looked rediculous, but I was trying to save money. I didn't grow an inch over the next couple of years, and ended up getting rid of the shirt before it actually fit me (oh, and btw I am not much older than you). So, buying big didn't help me. I decided that I didn't like the shirt before I grew into it. A few months ago, I bought a pair of To Boot New York captoe oxfords-dress shoes, which I also wear with jeans a lot. I got them on sale, and spent about $150 on them (vs. $250, I think). Not over-the-top expensive, so I can afford to replace them in a few years if I outgrow them (supposedly, guys continue growing until their mid-20's, so it might happen). Also, since they are a fairly stable article of clothing, I don't have to worry that they will look dated in a couple of years. In summary: if you still have growing potential, take that into account before you drop big bucks. Since you are young, like me, your fashion tastes will change rapidly, so don't drop bucks on casual shirts, jackets, jeans, or anything else trendy (save the money for a couple of high-quality suits and some well-made oxfords or bluchers). Oh, and never spend a lot of money on one brand at one time. Hard experience has taught me that.