I’m always on the hunt for new hats, so that usually means I come across the latest trends whether I like it or not. Well, wandering through the accessories page of Shopbop the other day, I came across this: a bucket hat styled with a chic red lip and a striped top. The message was clear; it intended to lure me into the illusion that this is a trend I won’t regret.

But the bucket hat goes too far back for me, and is a trend I already regret! From my middle school love of butterfly clips, faux hair and quirky dELiA*s catalogs, the style is just something I associate with my awkward youth and embarrassed blushes when looking through old photos. I’ve been watching in slow motion as 90’s styles have come back in vogue and it’s been a weird and wonderful thing. I’m pretty nostalgic about the music from that time, but whenever I see the Matrix glasses on Bella Hadid, I am just not feeling it. (I do like that movie, so for that, it works).

The bucket hat, however, brings up just too many things. From the Wheatus video for Teenage Dirtbag to N*Sync’s Justin Timberlake, and the album cover of the one-hit-wonder band New Radicals (with the N reversed, of course!), I associate a lot of the look with music. I also have a vivid memory of a bucket hat Jon would wear on vacations when we first started dating. It was often paired with high socks and sneakers at the beach, and it’s an image that will forever be associated with those kinds of hats.

Speak to me again in five months, and see if I’ve cracked. I doubt it though…

Would you wear a bucket hat? Share with me in the comments below! And to see more hats that are a better fit for a timeless style, click here! Image courtesy of Shopbop.