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Stepping Up My Style... Where to start?
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I think the move from boy's clothes to man's clothes needs to be faster and bolder. At this point it doesn't help you just to buy more expensive casual stuff. You're ready for shoes that are NOT sneakers, pants that are NOT jeans, and a jacket you can wear with a tie.
The other suggestions people have given are a good path to follow--get some clothes you can wear in a professional office setting like a sport coat, dress shirt, (slim) chinos, and oxfords. In Europe you can use Massimo Dutti as a starting point--their dressy stuff is low quality, but at least it mimics a quality look.
I think Chelsea boots are a joke--really, elastic boots??--but I may be alone on that.