You can dress superbly without shelling out $20K a year. You might have to spend $15K to initially build the wardrobe, but unless it is a hobby (believe it or not, I like looking and trying on more than actually buying) once you hit a threshold (10 suits, 20 shirts, 50 ties, 7 or 8 pairs of shoes) it isn't necessary to continue to build your business wardrobe. It is more an exercise in gradual replacement. You could easily buy 10 superb OTR suits for $10,000 total (including tailoring), 20 MTM shirts from WW Chan for $1800, 50 first class ties bought on Ebay for $1500, and 8 pairs of CJ handgrades from Plal.com for $3200. That's $16,500, and that would be getting really superb stuff at nice prices, but not tremendous prices. That's really not that much money for a first year lawyer at a big firm. Now, knock that total number of suits from 10 to 8, and all of the sudden you can get possibly two true bespoke suits (depeding on where you live) instead of 4 OTR and spend the same amount of money. I would not recommend doing this, however, unless and until you appreciate the garment. Unless you are filthy rich, I don't believe you should purchase something just because it's the best. You should purchase it because you appreciate why it's the best. If you can't avoid spilling alcohol on yourself after work, then I think it is likely you wouldn't appreciate a bespoke suit as much as you probably should before you get one. So, my answer would be: No bespoke suits until you decide that a life spent spilling alcohol after work is not the one for you.