750 - ToJ Leather (grey collared moto because Black is too easy) Outerwear TOTAL: 750 500 - CP Training Boots 600 - Paul Smith/Marc Jacobs/F+B boots in brown 300 - RMW Black French Veal Chelseas 100 - Grey suede Nike Blazers (or GATs if you prefer) Shoes TOTAL: 1500 50 - Uniqlo Chinos in khaki 50 - Uniqlo T-000 white colored denim 50 - Levis 511 (cheap beaters) 250 - Random denim brand (Ande Whall? ) Bottoms TOTAL: 400 450 - Thick as Thieves Suit (navy) 250 - Uniqlo J+ Suit (grey) Formal TOTAL: 700 300 - NdG Sweater 150 - All Saints knit 150 - All Saints knit Knits TOTAL: 600 200 - Uniqlo Shirts X5 (~ 40 apiece right?) 150 - All Saints shirt 20 - Hanes V-Neck (2x three pack) Basics Total: 370 Ok so that's 3920, give or take 4K with tax and some approximating of prices. That builds a pretty good wardrobe and not filling it with cheap junk like Desert boots either. The last 1K can be dumped into some awesome grail pieces (expensive knits, more leathers) or whatever. The only thing else I would add is some lightweight jacket, maybe like a trench either on the cheap end (Uniqlo like 150?) or grab it in a cooler brand. And of course this is all retail pricing, so slash this to 60% if we're counting sales.