I definitely think I have enough clothing, and I'm the same way -- I hate shopping because nothing seems to ever fit me properly, and I usually don't like current styles. I'd have no problem wearing jeans or kahkis and plain t-shirts or polo shirts every day.
Where I run into problems is when it comes to work or special occasions -- I tend to dress down more than I should at work (though I have a fairly active job, needing to move around a lot, so it's important I be comfortable), and for special occasions I never seem to have anything appropriate that I like, so I end up buying something the day-of on impulse that afterward I realize I don't like so much.
no subject
Where I run into problems is when it comes to work or special occasions -- I tend to dress down more than I should at work (though I have a fairly active job, needing to move around a lot, so it's important I be comfortable), and for special occasions I never seem to have anything appropriate that I like, so I end up buying something the day-of on impulse that afterward I realize I don't like so much.