Depends on how much you figure your needs in clothes - if you go for a full wardrobe (even minimal) there is a significant investment, if you go gradually, you will find that you spend a lot on junk - bad shoes, bad suits, bad etc. Audit your wardrobe in parallel with your spending habits and plan it throughly - on a 5 year base. Start with a suit - full bespoke - and one MTM (or entry level bespoke, as offered by Kilgour for example). For me going bespoke with shirts is not a priority, so phase that for the end. Shoes the same, go that in the middle. My grandmother had a saying - I am too poor to buy anything else than english fabrics. Buy quality and it will last - MBA speak, it will cost you less per wearing than a glued RTW garment. If your planning is good, you will end with a decent wardrobe - my count is 5 city suits, 2 sports, 6 sports jackets, 10 dressed slacks, plus 2 dozens of good quality shirts in 5 years with the same financial effort that buying off the rack will do (given the junk we buy because it is on sale, etc). Even in the high end bespoke you find a part of the price to be paid for the "label" - saw that when I've compared a friend's Kiton cashmere OTR sports jacket with one of mine, custom made by a local tailor - my fit was better, the fabric was comparable (bought by me) - price advantage for the large, mine. Good luck!