I think this is my fifth attempt to write this post. If you’re reading this because it somehow bypassed my neuroses and is now on the public Internet, please know the struggle was real.

For about a year, I’ve been trying to compose my thoughts about ironic modern preppy, preppy vs. Prep, and my complicated feelings about labels like ‘preppy.’ I always feel like the posts fall short. The last thing I want is to come across as snobby or to offend anyone. Sarah at Fewer & Better (a previous Style Profile guest here!) recently wrote an amazing post about irony and the ‘ironic Boat & Tote’ trend and also encouraged me to try again with my own tangential post. So here goes!

All the talk about the latest iteration of ‘preppy is back’ seems to revolve very heavily around irony. Which is fine, if that floats your Chris-Craft. I have a very dry/sarcastic sense of humor in my everyday real life and am no stranger to irony. Liking things ironically is nothing new under the sun of course – the ironic tote trend kept ringing a bell, and I remembered this post from Stuff White People Like in 2008. (A blog name that didn’t age well.)

It’s not just the totes either – I’m thinking of the Rowing Blazers aesthetic and the boat shoes styled to look more like regular sneakers and the new takes on tweed suits. If you genuinely love the urban preppy trend, then enjoy your looks with zero judgment from me.

That said, the thing that rubs me the wrong way about ‘liking things ironically’ is that it seems to be more about making fun of other people’s taste than about liking something. It’s just a way of saying ‘this is lame and worn by undesirable people, yet I’m condescending to wear it, too. But I’m cool and not boring, so my wearing it is a joke.’

Considering that I very unironically have always worn pearls and carried canvas totes like my foremothers, ‘preppy as irony’ is not my favorite sentiment. I can’t say I necessarily care what people think of my clothes or style. I try to dress appropriately for the occasion and take care with my appearance. But beyond that, I’m just happy to enjoy what I (unironically) enjoy.

Being in my thirties is probably a big part of not caring. Back in 2008, when the SWPL post I linked above was written, I was 24. This was when ‘ironic liking’ first (??) came into fashion, and I definitely did worry that my tastes weren’t cool enough. My solution in 2008 was to wear a ‘fcuk in Boston’ T-shirt from the Newbury Street French Connection. High comedy, indeed, young me. At least the Boat & Totes are practical.

Another thing that I find…? Maybe ‘confusing’ is the right word? ‘Preppy’ seems to come back into mainstream fashion as a novel trend once every ten years or so, but the current version making the rounds has been altered to be quite a bit trendier than preppy revivals in the past. This misses the point of preppy, which is a quintessentially timeless style. I suppose it’s like any other trend – people who enjoy trends will wear ‘modern preppy’ and those who’ve always dressed in preppy attire will carry on.

The word ‘preppy’ drives me a little nuts also, but that’s a whole other unpublished blog post (actually, three of them, deleted prior to publishing). I started out the blog and Instagram vowing to never use the term, but wow, #preppy gets a lot of reach. So I caved. The algorithm is hard enough to cut through.

Questions for the crowd – what do you think of the modern preppy and ironic tote trends? Would you like to read a post delving into labels like ‘preppy’? Does anyone know if ironic liking was a thing prior to the mid-2000s? Please let me know!