Buy or construct extra closet space. Abundant supply is the foundation upon which a surprising outfit may be regularly built. Plan your outfit for the day around that accessory. Be it stockings or neckties, hats or suspenders, make that accessory your fashion trademark. My own choice, of course, has been neckties .
Clothing is made to be fashionable in a season.
Do not entirely scorn the Salvation Army stores and such, but travel on occasion to wealthy suburbs and you will be richly rewarded in fine clothing at reasonable prices. I know a man who used to go to England every year and buy a used Rolls Royce for a couple of thousand dollars, then ship it back to the U.S., drive it for a year and then sell it to finance his next trip and buy another. He always had money left over and by the time I met him often bought two or more cars. It worked for years, and so I incorporated his insight into my theory. Remember to have a fashionable outfit.