Ask Lemmy

There are a couple of replies with good advice here. I'm going to add to them. First, remember that you don't have to get everything at one go. It takes time to build style (notice I say that instead of fashion).

Not all body types can get a good fit off the rack, but having your clothes fit is probably the most important thing you can do. It's not expensive to have shirts tailored. I have a long torso and narrow shoulders, so any of my work clothes or going out clothes are purchased a size too large and taken down to this very nice Chinese woman who takes them all in for me. It runs me about $25 per shirt to do it but I get a lot of wear out of them so it's worth it.

Build a capsule wardrobe. A couple of nice plain white T-shirts (I happen to like 3 fit theory because of their range of sizes, but if you can buy off the rack almost any decent T-shirt will work) and a few different colors that you can swap between create a base to build around. Get a couple of dress shirts, one in white (my other go to is blue, but I've really gotten into a pink dress shirt under my sweater for cooler weather). Get some good fitting jeans, charcoal slacks (or a charcoal suit), and some brown, khaki, or olive chinos and have them hemmed. From there you can get casual button up shirts, a cardigan, and a nice sweater. You'll also need casual footwear (I wear skater shoes), dress shoes, and maybe some brown leather boots (I wear Western boots but I don't recommend it unless you are either very comfortable in them or are somewhere that they're common....get some reasonable lace up boots).

Mix and match everything. At this point you'll never look like you're wearing the same outfit twice. You'll look put together and you'll have style. Layer your casual button up over one of the T-shirts. Layer the sweaters over any of your button up shirts. Tuck in if the occasion calls for it. Layer the sweater over a T-shirt.

This advice obviously isn't for everyone, but you'll look good. I get compliments about how put together I always look and honestly I rarely stop to think about what I'm wearing because almost everything in my closet goes with everything else and it all fits. With mixing and matching everything I probably have a ton of ways I can put things together with less than 20 items of clothing, 3 of them being shoes.

On any given day it's easy for me to go from my desk job, to giving a demonstration to executives, to the ranch to ride some horses, then out to any bar in the city. Of course not all of these will apply to you. But if you take your time over the next several months you can get one item on payday and build things up and have something to wear anywhere.