I have had my high top black converse for around 4 yrs and they have in recent days gone from perfectly worn in and my favorite shoes to pretty grungy and less in the rotation. There is a fine line for me between the right amount of scuffs and wear and tear and being able to wear something to work without offending a client (although as a designer you can get away with a little more because you are one of those "creative types"). But the dilemma is which shoe will be brought in as replacements...i LOVE the idea of gray high tops (has to be a high top) but i always come back to photos of the all black pair like this photo (ill take the whole outfit too!). But i never wear black so they just seem SO BLACK. I just wish they didn't take sooo long to get the perfect point...NEW tennis shoes are so squeaky clean and goofy looking. At least for converse. I had bought a red pair before (was very into The Strokes at the time and Nick rocked the red) and had to give them away because they were so new they looked like clown shoes and i would always put them on for five minutes and then retire them back to the closet.