3 Keepers & a Regret: Lindsay Sword
Five cities. Ten days. One carry-on. And a boss.
3 Keepers and a Regret is a recurring conversation where I ask people I admire to name 3 things they’d fight to keep — bought, inherited, stolen — and 1 thing they regret.
When I was planning a 3-country work trip I was excited. Until my boss told me I couldn’t check a bag. My fear of what I couldn’t take started talking, and I tried to back-out, unsuccessfully. Then I came across Lindsay Sword from Fashion Soup. She’s one of the only style writers I’ve found who doesn’t pretend price doesn’t matter — her perfect white tee is $14.90 from Uniqlo.
Lindsay packed for a 10-day trip work trip with only a carry-on. She knows her style, picks her looks in advance and packs accordingly. All of which for me is a real struggle. On the plane she wore pull-on pants. I now own three pair.
Here’s Lindsay, who had it figured out days in advance while I’m still packing on the way to the airport.
Three Keepers
No. 1 — Dad’s sweatshirt
This sweatshirt is my most prized piece. It was my dad’s from business school, and is fifty years old. There are holes everywhere, and while I used to wear it all the time, now I’m nervous that it will completely disintegrate, so it lives mainly in my drawer. A grey raglan sweatshirt is probably my #1 style. I think it goes with absolutely everything.
No. 2 — Dries Van Noten blazer
I am a Blazer Person through and through. I found this Dries Van Noten peak lapel chocolate brown blazer on sale a few years ago, and it is a magical garment: I always feel good when I wear it. I decided to make this my first day outfit at my new job last year — 12 years after my last first day at a new job.
It makes me feel confident and polished, which was exactly how I needed to feel.
No. 3 — Brooks Brothers boys button-down shirt
I bought this Brooks Brothers boys button-down shirt last year in the spring drop of our Vintage Shop. It’s from the 1960s(!), and I love the soft green color and ivory stripes. The quality, no surprise, is amazing and all the century-old hallmarks of a Brooks Brother’s button-down are there: oxford cloth, button-down collar, and 6-pleat shirring at the barrel cuff.
It reminds me of the history of fashion and the through-line to today.
One Regret
This is such an interesting question, and as I reflect on it, I realized I don’t really regret any of my purchases! Everything I’ve bought has helped me get one step closer to identifying my style and what’s feels right in my closet. I shop both by instinct and intention, and each process has a place in my personal style.
I suppose I’ve regretted a few dress purchases, just because I never seem to want to wear a dress when I could wear a cool jacket and pants!
Why I’m Still Shopping
Lindsay doesn't really regret her dress purchases, and I believe her. She shopped her way to knowing herself. I want to become comfortable enough in my own skin that I see my patterns and know what to avoid. Including the items in my closet still wearing their price tags.
So many of us are still discovering. We’re buying for the version of ourselves we think we should be. And until we accept who we are, we’ll keep shopping for the stuff that stays in the closet.
Thanks to Lindsay Sword — subscribe to Fashion Soup to learn why the challenge of jean shorts is real.
Rani, I was so honored to be asked to contribute to this series, thank you and thank you for your very kind words, they mean so much!