I'm a big nerd, and created an extensive Excel spreadsheet of my wardrobe to deal with a similar situation. It helped me to get a concrete sense of what I had, what I needed, and where I could trim the existing wardrobe. One of my largest concerns was that I could cover the seasons, which in New York violently fluctuate. I created columns for each month, then marked which months would be suitable for every item. I found that I was way too light in summer clothes, and needed a good fall sportcoat, so over about six months I ordered a Spring/Summer navy-blue windowpane suit, a beige linen summer suit, and a yellowish-green herringbone tweed jacket for fall/winter. I'm a big fan of custom here because it allows you to have exactly what you're looking for, without compromises. My budget doesn't stretch much either though, so I've had to be creative (see the current experiment with Vaish) All told those three were under $1000. It also lent me some discipline with purchases. I forced myself to pass up some beautiful shoes at the PS sale because I really need black shoes. My guide is to only buy it if it fills a hole or replaces a dying garment. At the same time, I try to plan ahead for clothing purchases. For example, if the budget stretches, I'll try to get some more summer trousers in July, maybe even a new sportcoat or suit. I also need to get some more grey flannels for the fall, and perhaps another suit or jacket. I also track my daily wear, and run the numbers to see how often I use items (suits, shirts, ties, & shoes). I'm finding that variety is great and something to shoot for, but how much you like an item is MUCH more important. I wear my favorite ties two or three times as frequently as the others, which are practically painful to wear. Only buy it if you really LOVE it. Forgot about the deal. You won't care if it's a deal when you're sleepy and need to put together an outfit that is both appropriate and brightens your day. Combined with the rules above, it works well. This also helps clarify hits and misses. The mtm beige shirt and brown flannel trousers, regardless of how well they fit (very) or the deal (also excellent in one sense, at about $150 for both), were a huge mistake. They don't look good on me. I never wear them. Now I will avoid brown for suits, and lean back towards grey and navy, which look much better, and I revert to with frequency. A lot of this is common sense, but for me, the on-screen presentation helps reinforce it.