My daughter spent this past summer interning for a global security firm in McLean, Virginia.
Twenty-four hours before her first day, she was exactly who she’d been for the previous three years in Malibu, beachy blonde waves, jean shorts, tank tops, and flip-flops. If you’ve spent any time here, you know “formal” in Malibu means maybe tucking in a shirttail. If you even have one. A day later, she was commuting from Washington, D.C. into McLean each morning in a black blazer, tailored trousers, and heels.
Well. Sort of.
The heels weren’t actually on her feet. They were tucked inside her designer tote next to her lunch bag, hidden beneath the polished exterior alongside the tennis shoes she wore on the Metro every morning and changed out of once she got to the office.
Her own Tess McGill, Working Girl moment.
My husband had given her that lunch bag for her birthday before she left for D.C. Talk about full circle. Long gone are the days of the monogrammed Pottery Barn Kids lunchbox and the matching backpack that looked almost as big as her little body. Today it’s a sleek neoprene lunch bag tucked inside a designer tote.
The contents, though, have barely changed.
Turkey. Sliced strawberries. Cucumbers. Crackers. And two Hershey’s Kisses.
Some things don’t change, even at twenty-one.
Her internship has since come to an end. The blazers are packed away, and she’s back in Malibu getting ready for her senior year in college. Which means that, like so many families this time of year, we’re preparing for another beginning.
Depending on where you are in the world right now, there’s an anticipatory feeling in the air. Excitement laced with apprehension, a thread of insecurity underneath it all. It’s back-to-school season in the States. And for some, it isn’t just back to school. It marks the start of a major life pivot. The first day of a professional career, or in my daughter Elise’s case, the beginning of the end. The countdown toward college graduation and the next chapter. We’ve been slowly preparing since late last spring.
The truth is, everyone’s mostly just figuring it out. Part of it is playing a role. A little fake it till you make it. You dress the part. But in your own way.
As parents, we spend years preparing our kids for these moments. We teach them to drive. We help them choose colleges. We talk about careers, and we remind them to be kind, to work hard, to say thank you. What I didn’t expect was that one of the biggest confidence builders would come from something as simple as getting dressed.
I’ll be honest, and sorry, Elise, my budding career gal doesn’t see what her closet holds with the same eye I do. So there was work to do. Not to buy her a whole new wardrobe, but to train her eye, to build from what she already had and assemble it each day for a successful professional summer. Because being the new kid in the cubicle isn’t easy. Neither is walking onto a college or high school campus feeling like you don’t look the part.
And trust me, this isn’t about how to fit in. It’s about how to feel confident upon arrival, whatever your vibe is.
We often joke in our house that the umbilical cord is still attached. And I’m beyond grateful for the relationship I have with my daughter. It’s not one I have with my own mother. That one is complicated, and she’s been absent for much of my life. Having a close relationship with Elise is the greatest gift.
And if I’m being honest with myself, I’m sure I go the extra mile to be the mother for her that I longed for in my own life, which undoubtedly means doing too much for her sometimes. She lets me know when I’m overstepping, and I’m also learning to let go. It’s not an easy thing to do.
I always say the biggest job as a parent is to raise independent children. Letting them take the wheel is the double-edged sword we have to learn to carry. And this summer, between my travel schedule and my desire to see her take charge, we needed a plan. One that didn’t have her calling me every night, or in the middle of a wardrobe crisis: WHAT DO I WEAR TODAY? It was imperative for both of us. So we built a plan. And here’s how we did it.
It started with a lesson I’d learned thirty years earlier, from a magazine.
Long before Pinterest, Instagram, TikTok, or any wardrobe app, there was one feature I looked forward to every single month inside InStyle. It was called Instant Style. If you’re old enough to remember those pages inside that 100-page glossy rag, you probably just smiled. They were always some of my favorite pages, and the recreations of them floating around social now still make me pause.
Those pages fascinated me. Not because they featured expensive clothes, and not because they told me what was fashionable. Because they showed me possibilities. One blazer, three outfits, a handful of basics mixed together in ways I never would have thought of on my own.
Looking back, I don’t think they were really teaching style. They were teaching perspective. That a great wardrobe was never about owning more. It was about seeing what you already owned differently.
Thirty years later, I found myself trying to teach Elise the very same lesson. Not because I wanted her to become someone she wasn’t. Quite the opposite. I wanted her to walk into that office feeling like herself. Confident, prepared, able to spend her mental energy on the work instead of on whether she’d chosen the right outfit.
That’s when I introduced her to an app called Stylebook. Instead of standing in front of her closet every morning trying to remember what she owned, she photographed every piece, organized it by category, and started building outfits in advance. She could mix and match what she already had, plan a whole week in a few minutes, and pack for a trip without leaving half her wardrobe behind.
And somewhere in there, she stopped saying she had nothing to wear. Because for the first time, she could see everything she already owned.
Then something funny happened. She showed it to her stepsister. Her stepsister showed a few friends. Those friends showed other friends. Now there’s a whole group of college students and young professionals using it, each for their own reason: planning internships, getting through sorority recruitment, avoiding the overpacked suitcase, or just rediscovering clothes they forgot they owned.
Watching it spread reminded me of those old Instant Style pages. The technology changed. The lesson didn’t.
Confidence rarely comes from having more. More clothes. More shoes. More options. More often, it comes from removing unnecessary decisions.
Because the first day of school is stressful enough. The first internship is stressful enough. The first job is stressful enough. If fifteen minutes on a Sunday means you get to spend Monday morning thinking about your work instead of your wardrobe, that’s a pretty good return.
Clothes don’t determine your worth. They don’t make you smarter, or kinder, or more capable. But they can remove one unnecessary distraction. And sometimes that’s exactly what confidence looks like.
As for Elise, the internship is over. The blazers are back in the closet. The tennis shoes have reclaimed their rightful place. And somewhere inside a designer tote sits a sleek little lunch bag carrying turkey, strawberries, cucumbers, crackers…
…and two Hershey’s Kisses.
Apparently some things are worth keeping exactly the same.
Always EDITing,
Leslie
I love reading your comments. Drop me one or leave your own Instant Style hack.
P.S. I'm getting ready to leave Malibu. This is always the hard part. Goodbyes never get easier. Being an empty nester is a whole nother article, one I plan to tackle on my flight home. Tears and all.
I couldn’t download this app fast enough. But photographing my whole closet???
Did I understand this correctly? Did your daughter create an app from that experience? I have a degree in fashion design, although you wouldn't guess it by the way I dress. My uniform is ripped jeans and t-shirts. But I can dress up. I'd be motivated to dress better if my weight was down. But that magazine spread brought back memories! I used to buy every fashion mag. Every. Month. I loved the fashion layouts. The colours. The textures. The titles on the spreads. I always loved the wordplay. The tongue in cheek! Mostly cheek! That's one thing I love about writing on Substack. Titling my posts. You're always going to get me with a snappy title.