If I had to choose between clothes and shoes, I would happily don a burlap sack for the rest of my life. This creates a problem because A) you can never have enough shoes and B) shoes can be expensive. So, I've made a rule that I will only pull out my credit card for truly fantastic shoes.
But, what makes a shoe fantastic? For me, they have to have some element of surprise— a great color, an interesting heel, something that looks different from what every other girl is wearing. They also have to be well-made— leather soles, suede-lined heels, sturdy straps.
I'll admit that I spend more on shoes than the average person, but I really think it's the best way to invest in your wardrobe. For one, your shoe size does not fluctuate like your weight can, so one pair of shoes will fit pretty much forever. Secondly, if the shoes are well-made, they will last for years with the occasional repair. And if they are gorgeous, they will be classic.
(photo © http://thesartorialist.blogspot.com/)
I recently saw the above photo of Anna Dello Russo, Fashion Director of Vogue Nippon on The Sartorialist, wearing these amazing shoes with cherries on them. I assumed they were shoes that had just walked down the runway 5 seconds ago, so I was surprised to find out they were Yves Saint Laurent from 2003. Six years later the shoes were still eye-catching, not because they were trendy, but because they were beautiful.
Another shot of the shoes from Garance Doré.