[zyxley]

Being conscious about your clothes really helps if you don't like dealing with fashion, paradoxically enough, since it means you can make your choices ahead of time. Try different things until you find one brand you really like, and then direct order different variations in that brand in the sizes that you already know fit you well.

To go a bit further, I have several completely identical pairs of wrinkle-free all-weather slacks in neutral colors that match with everything. They fit me well and look good on me - and now for most outfits I just don't have to think about what pants to wear.

Similarly, I've got a pair of waterproofed leather Oxfords that are nice enough for formal wear, low-key enough for casual wear, and sturdy (and grippy) enough for everything up to light hiking, so for most things I just can just wear the same pair of (very comfortably broken in) shoes.