Do you ever think about how, in the present moment, everything you like, everything you are, the way you dress and look— all represent something that you could potentially be embarrassed by in future years? In OIAM, I wrote about how I often look back and laugh at my sense of style; how could I have ever thought the fleeting trends/fads I participated in were the exception? Why did I think my Michael Kors outlet mall oversized watch collection would stand the test of timepieces? I think it all started when I found a dress that resembled the personal style of one of my favorite early influencers, Minnie Mouse. My pose here tells you everything you need to know about an outfit's power over me. I was such a shy girl, but this breezy shoulder lean is giving snowMan! I feel like a woman.
I hated that, but I guess I’ll leave it since I’m trying to keep it caj on Substack.
It was so cute: a white t-shirt and white biker shorts attached to an apron-style polka dot dress. Fashion meets function! The club meets cartwheels! I couldn’t believe my mom agreed to get it for me and I was convinced I’d wear it forever. And to say I wore this dress often would be an understatement because I quite literally wore it everywhere until I wore it out, regardless of context. For example, I believe in the photo below, I wore it to go fishing. More importantly, peep the Mondo I’m sipping, though I believe I preferred a Squeez-It at the time. They really don’t make sugar water like they used to.
On this week’s Be There in Five podcast episode (Total Eclipse of the Scarf), Caroline Moss and I discuss this phenomenon, only to realize we’ve literally talked about it on nearly every episode we’ve ever recorded together. We’re delusional about how timeless we are, and we’re apparently forgetful about how many times we’ve already talked about wanting to be timeless. But I think this is the ultimate long con of fashion: believing that a particular brand, silhouette, or style has cracked the code. Finally, fashion has been solved! If I buy this one thing now, I won’t have to participate in trends going forward since I will obviously dress like Minnie Mouse for the rest of the time.
I think there's such charm in our delusion for the timelessness of now. The Vera Bradley purse I spent my whole paycheck on, the way I thought a pair of platform Rocket Dogs would launch me into another stratosphere of popularity, the wounds I genuinely thought I healed by wearing bandage dresses in 2012. As we’ve discussed, when it comes to most photos of me, you don’t have to cut me open and count the rings to know EXACTLY what year it’s from. Any guesses?
Since I often felt insecure as a young woman moving through the world, the times when I felt like hot shit are particularly memorable to me, even though the outfits are far from it. In the summer of 2006, I put the MOST thought into how to up my style game to appear more classic and sophisticated for Kelly and I’s first trip to New York together. I spent *for, like, ever* planning my outfit in case the paparazzi mistook us for young starlets or socialites. I needed to blend in but stand out; I needed to be on trend but not try too hard. After a lifetime of being allergic to apples, I fearlessly took a bite out of the Big one and debuted this outfit:
It’s…. a white tube top and chandelier earrings? But like my pan-friend side bang, I thought I looked SO hot despite now realizing it fell flat. All that matters is how I felt, and I remember being worried I’d fit in so seamlessly as a local I’d be asked for directions. We flew coach and then searched for its namesake fake wristlets in Chinatown, along with Chanel bags, Burberry scarves, and Tiffany/Trffany necklaces found in New York’s hottest Dateline episode waiting to happen: an unmarked white van. After a long day of shopping, we went to dinner and took Coco Canal Street’s finest to the theater. Not Broadway, but rather the AMC Kip’s Bay, where we saw You, Me, and Dupree in theaters, as locals do. But it wasn’t just me who was feelin’ myself and my classic style; Kelly liked this halter top so much that she bought it in SEVEN colors from New York & Company. One for every day of the week! You really have to believe in something’s longevity to need it in light pink AND magenta.
But as far as we were concerned, New York was blessed to be in the Company of two fashion icons. What’s that away message quote, the tans may fade, but the devotion to halter and tube tops lasts forever?
My delusion toward timelessness is perhaps best evidenced by what I’ve chosen to wear during professional photoshoots over the years. In 2016, we asked the photographer to take new corporate headshots for us individually after taking our engagement photos. While my then-fiance-now-husband had the foresight to change his blazer and shirt throughout the session, I doubled down on this off-the-shoulder chambray dress that literally everyone I knew already owned. In hindsight, it’s more 2016 than the Chainsmokers, and it’s clear by my exposed clavicles in the workplace that I was so ready to usher in our first female president. Even though that dress (may she rest) kicked the bucket in late 2016, along with my hopes and dreams, I’m charmed that I thought I looked so damn good that I kept it on for my engagement photos, save the dates, AND headshots, pigeonholing myself into this look both personally and professionally for the next several years until I could afford another photoshoot.
To be clear, I still think I look cute, and if you like wearing this dress, so do you! My point is that I have a tendency to double down on trendier pieces I’m convinced I’ll love forever, but 1. by pursuing items that everyone else already has and then 2. overwearing them, my interest deflates faster than the number balloons behind me. Mostly because I didn’t know they required helium, and right before our romantic photoshoot I had a small meltdown while blowing them up manually, only for them not to float. I had to tape them to a sheet behind us to get the same effect. Per the theme of this essay, at the time, the trend of using oversized gold number or letter balloons to commemorate life milestones didn’t feel optional; it was a way of life.
The joke is, I genuinely still believe all the time that I’ve finally hit my style stride, especially now that I’m past age thirty-five. If I’m old enough to rule the free world, surely I’ve learned by now I’ll never be boho-breezy enough to shop at Free People. To a degree this is true; I’ve refined my taste and now have more uniform-style dressing I can stand by, even if my jeans are too stiff for sitting. In recent years, I’ve narrowed down my personal style to what I like to call “grunge keynote speaker.” It’s kind of like Steve-doesn’t-have-a-Job, where you rock a classic black top and light-wash denim but maintain a youthful edge by participating in things the school dress code used to forbid, like distressed jeans and too many piercings.
I’m laughing as I type this because I went to find this picture as an example of how I’ve learned to stick to more simple outfits to avoid the photos on my website not seeming current. Yet suddenly, I feel strongly that Steve’s jeans would’ve been the more chic, timeless option for me. My skinny jeans are boa-constricting my calves and could easily be carbon-dated to the pre-pandemic era. WILL I EVER LEARN?!
The thing is, it doesn’t matter; we should wear what we like and prioritize what fits us over what fits in, and the least cool thing we could be doing is worrying about whether other people think we’re cool. I hate the mockery of side parts and skinny jeans and words like cheugy and basic and anything else that maligns our sartorial choices as a function of bad taste when we’re all just a product of our time. Not to mention how wasteful and expensive it would be to turn over one’s wardrobe year after year. But I’m not even talking about what other people think in this context; I’m mostly processing how weird it is that I always look back and think of former versions of me as cheesy and uninspired when, in the moment, I thought I WAS the moment. Similar to what Caroline expressed, I genuinely will convince myself at any point in time that I’m the coolest/hippest/youngest/freshest version of myself that’s ever existed, which I maybe just debunked by using words like “hip” and “fresh.” I assume I’ll look back on what I’m wearing now and see a woman in her prime in my matching set from Amazon Prime; I’ve come a long way from white vans to lightning-fast fashions that smell a little like formaldehyde.
Don’t even get me started on how this timelessness talk makes me tailspin when I think of it in the context of being a mom, because my feelings on this topic are deeply unresolved. On the one hand, I feel bad that I never really thought 90s moms (in my suburban VA reference group) were particularly stylish as a collective; I just thought they dressed like moms (except for my own mom, of course, because her version of 90s activewear was wearing wind suits in roller-rink arcade colors and they were fierce as hell).
Regardless, WTF does “dressing like a mom” even mean?! It didn’t click with me until I became a mom and would get dressed and think to myself, “I’m not like other moms, I’m still cool/hip/young/fresh” that I realized this misogyny is still buried deep within me, even after a child came out of me, and I’m sure literally all moms throughout time have dressed in a way that made them feel cute and comfortable and did not see themselves as wearers of “mom clothes.” In hindsight, they were humans wearing clothes who happened to be moms, but society often teaches us to define a mother’s aesthetic in a way that’s denigrating and desexualized and assumes she’s not more current because she’s busy with her kids and, therefore, must not have the time. Rage. Even if that were true, if my husband said I “let myself go” or insulted me for not maintaining my appearance due to time constraints that he’s responsible for by not contributing whatsoever to the maintenance of our home and family, I’d kindly tell him to “let himself go” play in traffic.
After Caroline and I chatted, I was looking through some old photos and came across this one from [what looks like] a school or extracurricular-related picnic in the 90s, and I had another timelessness spiral upon realizing that they are close to the age I am now. I didn’t recognize any of these women, but my dad is in the back grilling, wearing an outfit he could wear tomorrow, and I wouldn’t even think twice. But I’m having trouble computing why the women wearing shorts of the same length look more 90s than a strip mall containing both a Blockbuster and a CompUSA? I’m not trying to reduce them to their motherhood status nor imply a lack of self-maintenance; I just am questioning my hypothesis if most young moms in a given era assume they look cool/hip/fresh because I have an intense aversion to knee-length khaki shorts that transcends space and time, and I’m genuinely curious if these were objectively considered fashionable? Feel free to provide any insight in the comments, and I apologize if this offends any lovers of a pleat on a long dress short. In recent years, I have warmed up to a Kornacki khaki, so maybe I’m the one missing out.
I don’t have the answers, and this newsletter was literally just supposed to be 100 words telling you to listen to this week’s podcast episode, so I’m not entirely sure how I got here. I’m just a girl, standing in front of the internet, asking myself if I’m delusional to think I’m doing something cuter or more timeless than the moms before me who apparently shopped at a nearby Talbots that happened to be inside a golf pro shop. If that’s the case, will we look back on our matching athleisure sets the same way and realize we were deLuluLemon all this time? I genuinely think modern activewear and athleisure are more fitted, classic, and functional, but I also felt that way about everything else I’ve ever worn or bought, from Arden B to Z Gallerie, so maybe it’s all an illusion.
I guess we’ll never know. But I do know I feel very guilty saying I hate those shorts and think millennial style is cuter, because everyone is usually just doing their best, and all that matters is that they liked them! Clearly, I’m still a millennial recovering from Y2K misogyny, and I struggle to reconcile my modern feminism with my internalized beliefs of yesteryear about mom clothes. It’s hard for me to look at outfits in general without overemphasizing the importance of fit and flattery. No matter how hard I try, it’s almost as if there’s a Stacy London bridge connecting current me to my inner 90s bitch who still thinks it’s “brave!” when women wear horizontal stripes.
I digress. The point is, I don’t really have a point. What else is new? I guess we're just always going to be a function of the time we're in, and it’s possible everything we love now will become something we'll look back on one day and find slightly dated or questionable. Although, at this point in life, to quote me in the 90s— I don’t even give a care. If I'm doing something now that I'll later be embarrassed by, maybe I’m doing myself a favor because, at the very least, it will be funny. It will give me something to podcast about from the nursing home at the space station. So maybe the greater service I could be doing to my future self isn’t trying to find that red-lip, classic thing that she likes, but to make her laugh instead. And to make her long for the confidence I have now, thinking I’ve finally achieved timelessness, even though I just swapped out my sock bun for a soap brow.
My favorite pastime is to reminisce about these moments in time because I now appreciate how there’s a hobbyist element to my participation in trends. I’ve had a great time most of the times I was trying to get with the times. (Are you there, Sallie? It’s me, Kate. I need an editor so I’ll stop saying the word time). Other times, I want to hug my younger self because the reason I took everything so seriously wasn’t because I was delusional; it was because I was after something deeper, like belonging. As I talked about in One in a Millennial, that’s one of the beautiful and bittersweet things about girlhood; sometimes, you have to take yourself seriously because no one else will.
Perhaps the only genuinely timeless quality we have is that we’re always changing. Or maybe it really is inherent to the millennial condition that our tendency to commit to a trend and follow the herd is why ‘cringe’ seems to be our leading descriptive word. But I don’t hate it. It implies earnestness, and I love that about us. I told my baby boy in the acknowledgments of my book that I hope someday my stories make him laugh and make him cringe, and I hope that he’ll do the same when he looks back on being a kid. As far as I’m concerned, if you cringe, it means you’re doing it right.
P.S. Listen to this week’s podcast episode here!
P.P.S. Support the show with this week’s sponsors and codes:
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Marc Fisher: Receive 20% off your purchase with code BETHEREINFIVE at marcfisherfootwear.com. (I’m currently loving these ballet flats, these studded slide sandals and these heeled slides!)
"I don't dress for women, I don’t dress for men. Lately, I’ve been dressing at Land’s End" is my favorite caption ever.
Love this, and am both deeply disturbed AND proud that I knew that scarf pic was circa 2011 before I even read the caption.