Don’t Mind Me… I’m Always a Little Overdressed

I was placing my chai latte order at Starbucks last week, wearing a button-up, colorful scarf, my good jeans, a pair of kitten heels, and my signature hoop earrings when a woman in leggings and a cropped t-shirt gave me the kind of look you’d give someone who showed up to a barbecue in a ball gown.

I know that look. I have gotten it before. It says, “Where do you think you’re going?” And my honest answer is, “Nowhere.” As a former fashion editor and longtime fan of great style, I’ve always dressed “up.” I see clothing as a way to express my personality, and I love the creativity of pulling together outfits that put me in a good mood.

Blame It on Zoom

In the past decade or so, it seems that casual has become the standard for style. I understand how it happened. The world shut down for a while, work went remote, and people began interacting on Zoom, often with cameras turned off.

A Lifetime of Dress Codes We Didn’t Write

In contrast, I think about where women my age started on their style journeys. Our mothers put on girdles to go grocery shopping… actual girdles, for nothing more than pushing a cart up and down an aisle. We came up right behind them and power-dressed our way into the ‘80s wearing shoulder pads, pantyhose, and pumps, because if we wanted a seat at the table we’d better look like we belonged in the room. We got “fixed up” for parties and events as a sign of respect for our hosts, and we wouldn’t have dreamed of stepping outside without make-up, because we were programmed to always look our best.

For much of our lives someone else has been setting the dress code: our mothers, corporate America, the unspoken rulebook that ties together appearance and success. So, when we reach our later years and career and culture stop writing the rules, the pressure to dress up fades away. For the first time in our adult lives, nobody is grading the outfit. And when nobody’s grading, we get a choice – shelve the style or wear it with conviction.

The Uniform of Surrender

A lot of women are letting it go, and I don’t mean that as an insult, I mean it as a description. The uniform of surrender may be stretched-out yoga pants with a torn half-zip or a giveaway t-shirt with a pair of clam-digger pants that could make even a tall woman look like she’s standing in a hole. These looks are comfortable, which is an absolute requirement. But they are also, if I’m honest, a little bit of giving up reframed as self-care. That’s not me.

Choosing the Other Direction

So I’m choosing the other direction. Not because I’m trying to look younger and certainly not because I’ve got money to burn on trends. It’s about deciding, on any given day with nowhere to be, that I am going to dress like the woman I actually am right now, which is vibrant and still very much in the game.

I hear the argument coming, because I’d make it myself if I were on the other side. I have earned the right to be comfortable. Decades of pantyhose and blazers and underwire, and now I get to opt out, so why wouldn’t I? Fair enough. But comfort and looking like a person who’s still paying attention to her own life aren’t mutually exclusive.

So yes, I may have been overdressed for a coffee shop filled with women hanging out after Pilates. I will probably be overdressed again this week, for something equally unremarkable. But I spent the first half of my life dressing for other people’s approval. I’d like this next phase to be all for me. If that means a woman in leggings gives me a funny look, I can live with that. I’ll just be the one who looks like she’s got somewhere fabulous to be, even when the only thing on the itinerary is running errands.

Let’s Have a Conversation:

Does style matter to you? Have you been given the “Where do you think you’re going?” look? What do you think is more important – comfort for the sake of comfort or expressing who you are in a way that makes you feel good about yourself?