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Yeah, absolutely! Let's see. I experienced the same thing with paradox of choice. Unfortunately the solution was just to spend a lot of time on it, trying different things and researching options by asking people and doing internet searches and browsing malls and outlets. Going from "no good clothes" to "all good clothes" took me a full year of off-and-on effort. Most important thing is finding things that fit. I did…
A TL;DR of OPs post: start simple. Visit /r/malefashionadvise and follow the basic starter guide, i.e. chinos, white oxford shirt, and leather shoes. You DO NOT need to spend 2.5k to look good: aim for 100-200 from ASOS.com and you'll look fabulous! You can order multiple sizes of the same product and return those that don't fit. Fit is key! Check eBay for good quality shoes if cost is an issue (e.g. Meermin, etc) as…
That amount is what I spent, but in the end now that I know what works I could burn it all and repurchase for probably $1200.