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Stepping Up My Style... Where to start?
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I would recommend not buying a ton of stuff immediately. Gradualism is huge when it comes to clothes. When I was younger I bought a lot of stuff I ended up never wearing. Still, that's part of the learning process.
I would view it as an experiment where you're constantly trying small new things and analyzing the result.
That said, you're talking about "investing" in dark jeans like, several steps down the road . . I think if you're wearing a t-shirt and jeans every day you can move faster than that.
Personally I don't like Chelsea boots but to each his own. I recommend upgrading from a t-shirt first . . . t-shirts are really underwear. That's how they began.
I recommend getting a collared shirt. The most versatile thing I own is a blue oxford button-down. I have three of them, actually, and wear them out and replace them all the time. You can wear it with jeans, with chinos, with sneakers, with nicer shoes, etc. You can roll up the sleeves in hot weather. You can put a sweater over it in cold weather. It's an all-season item. J. Crew's slim regular-weight oxford is great.
I don't really recommend getting a blazer unless one is appropriate at your workplace. I think blazer says "try-hard," unfortunately. There's just not a lot of call for it in everyday life. There are probably people making it work. You should probably work your way up to that though.
So I say start there and you can still wear your jeans and sneakers, etc., but then upgrade from there. I don't see how Chelsea boots would work with the other stuff you're wearing right now, whereas a nice button-down would.