Una, I still wear my Da Nang cargo skirts when no one is looking! Circa 2003. So comfy. In fact I think I will come up with a challenge for myself. Take a dated item and make it look now through styling individuality.

The ladies of Real Housewives of Orange County still wear those velour track suits, as well as the fitted tops, so I think there is some regionality.

I do think it depends a lot on context as said above. To me Natalie's skirt does look dated because of the way the hem sort of curls. Not terrible, but if you have a lot of better options why bother. The faded jeans with tight waist and taper don't just look dated, they look bad. I am sometimes attracted to bitsy flower prints and mentally do the would Elaine wear this test - I love Elaine and adored her style but it is time to move on. Fun topic!

Thanks everyone! This has been an eye opening and incredibly fun read! Honestly the last time I was "trendy" or interested in fashion was back in the 1980's in junior high, so like DonnaF I spent the last two decades in a fashion black hole. I mean I really was not paying attention to what was in during the 90's and 2000's. So that's why I had no idea that these bias cut skirts and mock turtlenecks were dated, because I've just been wearing them forever!

These lists are super funny. I definitely remember acid wash denim and scrunchies and feathered and crimped hair (and even those tapestry vests, LOL), but a lot of these trends just passed me by. Which I guess is a good thing. But what things am I wearing now that are going to be dated in 5-10 years? Hopefully not my whole closet! I just got it to where I'm happy with it!

Denise, you have an incredible sense of fashion history if you can remember all those details of when everything was in for one or two years! And that sounds like a great challenge to update a dated item. I'm going to post a thread about that and open up the challenge to the rest of the YLF group! I can't wait to see the results!

Anything worn by Kelly Bundy.

I try to avoid anything that has exaggerated details (such as really big shoulder pads or extremely pointy-toed shoes) that would link me to a certain point in time. I think the styles that have staying power are the ones that are versatile enough that you can make them look "fresh" (aka not dated) by mixing them with newer items in your wardrobe. Same goes with hairstyles and makeup colors/application.