I'd say it depends on the item and its quality. I have stuff i've worn for years and stuff that lasts a season. I invest more money in good-quality classics (suits, jackets, coats) that last a few seasons, but but trendier stuff isn't really worth the big splurge, unless I really fall in love with it.
Some classic things (like Chanel suit) I imagine I will be able to wear in a decade from now, same goes for quality leather handbags (I have some vintage pieces from my Grandma and they're still in good form and terribly chic). I clear out a lot of stuff each season and donate to a charity if I haven't really worn it or I decide I won't wear it anymore. Usually I stick by a rule that for each new item in, one thing has to go, so I try to avoid clutter.
Shoes are another matter, it is usually an irrational urge to get a new pair, and the more I have, the less I wear each pair so it automatically lasts longer. I get stuff like winter leather boots each year as they usually start showing wear&tear after a season, but classic evening heels usually last me for years. Same goes for really expensive high-quality shoes.