Let's go bottom up and I'll warn you I have fairly preppy style- Shoes - As Brian said can't go wrong with Chuck's. I've got a couple pairs of trainers (Reebok Classics, Gola, New Balance), good quality chelsea boots (brown and black), good quality dress-up shoe (I've got a really sweet pair of pointy slip-ons from Mario Giannini) that you can wear out to dinner or with a suit Pants - Jeans, you want several different washes and styles to add a little variety. I've got everything from a really narrow light denim to heavy fuller cut stuff. I've started to get into cords and love em.' Even if you don't go out or need to dress up a lot you'll still want a good quality pair of dress pants in black or charcoal. I really like slim cut trousers they go well with the pointy shoes... T-Shirts - get lot's of basics is simple colours (white, black, brown, etc) American Apparel and discount retailers like Winner's, Filiene's Basement, etc. are good for these. Always want to throw in some better ones for showing off. I love the fit and designs of RVCA and Lifetime brands. Shirts - can never go wrong with a rumpled dress or camp shirt (that's just a short-sleeve collared shirt). I like Rufus, Ben Sherman, and surprisingly Zara has some good stuff. Love polos too, Lacoste being my favourite for fit and finish, however they don't fit a lot of people well. Sweaters/Hoodies - I love knits, unfortunately before I knew better I purchased a lot of Hugo Boss, still fairly good sweaters, just paid too much for them. Really like hoodies and jackets from Lululemon (it's a yoga company). Have a lot of Mountain Equipment Co-op fleece hoodies and other pieces, great company. Jackets/Blazers - Love blazers, have a few thrift store ones. An unlined Donna Karen Signature cashmere and angora one being my favourite. If you live anywhere with a winter you always need a good overcoat. Try to get a vintage pea coat, and 3/4 length single breasted coat as well. Â I also have a vintage duffel coat (has horn hook and loops instead of buttons) and a snorkel coat (the coat with firm trim around the hood). I also love a good snowboarding jacket. I've got one now from Arson and I just ordered one from Arc'tyrex, sweet company. Accessories - scarfs are amazing, love wearing a big wool sweater and a scarf instead of jacket in the winter. Can never go wrong with vintage belts and a cool watch. Hope this helps (it sure was long enough). A.