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 NO

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 imho that's generally the large cost in the wardrobe.