Well, this is all going to be relative, depending on one's age, career, geographic location, body shape, and personal style. Â However, here is my list - coming from a 20 year old college student living in an area with COLD winters: 1. Â Pair of slim-fitting jeans with a slight boot-cut, dark wash with minimal fading (best to start out with light fading and let them get beat up over time, naturally). Â Preferably Paper Denim & Cloth. 2. Â Slim-cut suit, high-stance 2 button or 3-button with lapel rolled down to 2nd button, flat-front pants with slight flare at bottom, ventless or double vents. Â Black, for if you are going to be wearing this suit when 'going out', or navy/charcoal if you need to wear this suit for professional meetings. Â Jil Sander, Helmut Lang, or Gucci are all viable choices. 3. Â High-quality white dress shirt, herringbone pattern, possibly with french cuffs and full-spread collar. Â Again, this item must fit well. Â Turnbull & Asser, Barba, Brioni, Jil Sander, etc. are all good options. 4. Â Black or brown (depending on the suit color in #2) monk-strap shoes, with pointed toe. Â Preferrably slightly antiqued. Â I love my Gravati's, so I'm going to suggest this company. 5. Â White or black v-neck t-shirt. Â Cotton, and not too thin so as it's see-through. Â Jockey works just fine, or if you want to go upscale, Gucci or Prada. 6. Â A pair of trainers, for casual days. 7. Wool/cashmere blend 3/4 length coat in charcoal, or maybe black. Should hit right above the knees. Possibly with a ticket pocket. With these items, you should be able to create quite a few outfits for all sorts of occations. Â Wear the suit with the shoes and the white shirt. Â Wear the jeans, suit jacket, and dress shirt. Â Suit pants, v-neck tee, and shoes. Â V-neck, jeans, and trainers.