Start with a solid foundation of basics, some of which you probably already have. So what are basics? Well, think of them as the men's casual clothing equivalent of the basic food groups: jeans/pants, T-shirts, polo/knit shirts, and shorts.  Also, don't forget your basic accessories from belts, underwear, socks, and comfortable footwear. Resolve to keep your wardrobe of basics up to date. Once you've established a solid foundation, maintaining your basics should be relatively easy. You'll only need to buy a few items each year to stay in step.