The Case for Overdressing

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Hello, friends.

What a lovely time of year. Although times are feverish with fret, this delicious spate of weather is so appreciated. I adore Fall and its combination of warm, sunny days and a bit of a nip in the air. I love the anticipation for the holiday season and the Halloween kick-off. In my very brownstone Brooklyn neighborhood, the decorations are a delight.

I also got to try the Brooklyn outpost of iconic Ukrainian restaurant Veselka this weekend, and it got me thinking about how certain foods can be so comforting, like a breakfast of yolky egg and potato pierogies with a bit of avocado for an update. I didn’t grow up with pierogies, but something about their Eastern European cred feels right to my origin story (both sides of Eastern Europe, like many American Jews in this part of the country ). So delicious. I love old things. I love new things. I am neither nostalgic nor overly sentimental, but I love comfort, particularly when stimulated by sense. And sure, there’s great comfort in things that take you back to happy moments when you felt safe, warm, and loved.

On that note, I started thinking about comfort and its importance, which has become more essential post-pandemic. On Sunday, to accompany my breakfast of starchy goodness, I rocked an old pair of Nili Lotan drop-crotch sweats with a favorite Michael Stars poor boy-type cotton sweater, which felt divine. I started thinking about overdressing vs. underdressing, and I will dedicate both posts this week to discussing my thoughts on the above.

Have you ever heard the term “enclothed cognition”?

According to Wikipedia, Enclothed cognition is “the overall influence that clothing has on the wearer's psychological processes.” Enclothed cognition is the idea that what we wear influences how others see us and how we feel about ourselves. For instance, wearing formal or elegant clothes can make someone feel more competent, responsible, or disciplined. If you’re overdressed, this psychological effect can enhance feelings of sophistication, success, or glamour.

So, if we think about people who love to stand out, overdressing can boost confidence, attract attention, and even make you feel ready for anything. It also denotes a sense of power, control, and authority.

If we go back in time a bit, think of Marie Antoinette, whose decadent excess did not bode well, or the flappers of the 1920s, who rd the restrictive corsets and long gowns of the Edwardian era and adopted shorter hemlines, fringed dresses, and bold accessories like pearls and headbands In this way, overdressing was a form of rebellion against traditional femininity, marking freedom and independence and the better to make a dramatic entrance to The Stork Club.

Cut to the golden age of Hollywood when actresses like Marlene Dietrich and Audrey Hepburn overdressed with a formal and refined sense of sophistication. Dietrich, with her masculine suit and Hepburn’s Givenchy LBD in Breakfast at Tiffany’s, became the epitome of formal sophistication coupled with restraint. So you see, overdressing doesn’t have to be quite so "peacock”; it can also be incredibly elevated and refined.

And if we cut to now, think of the various fashion weeks and the endless peacocking outside the shows. Maximalists of the world unite. Think of Prince and Lady Gaga’s meat dress.

But history and celebrity aside, it’s also all about that “dopamine dressing” we craved after the pandemic. Think sequins for daytime or wearing luxe fabrics to an everyday event. I can’t help but think the poster child for this method of dress is Trinny Woodall, a successful and iconic cosmetics queen whose success is closely linked to her authenticity and ability to amp up her look with creative and unique self-expression. It’s also a great way to break out of wallflower syndrome and start conversations everywhere, from the street to a three-day conference.

By overdressing, you're turning an everyday situation into something that feels more purposeful or intentional. It's a way to turn mundane moments into significant ones, creating a sense of pleasure and joy, particularly when donning luxe fabrics like silk or sequins. Not to mention standing out in what many on social media are calling a “sea of same” thanks to TikTok trendlets and the constant “coreification” of style.

But most importantly, for women over 50, overdressing can be a form of rebellion against expectations that they should “fade into the background.” It’s a way of claiming visibility and vitality, celebrating life instead of being constrained by rules around how one “should” dress at a certain age. I think a lot about Carrie Bradshaw in “Sex and the City” and SJP, who often dresses down but looks terrific dressed up.

Kristen McMenamy and her endless Instagram selfie masquerade are just the epitome of overdressed and overdelivering when it comes to creativity and style on steroids.

Here are a few pieces that embody the vibe. Enjoy and sequins for breakfast (at Tiffany’s), please.

I may have featured this Simon Miller gold dress before, but I adore it and fantasize about wearing it to a weekday dinner and really going for it.

A velvet suit for daytime vs. evening is just so good. This feels a lot like Tom Ford for Gucci, but damn if I don’t just LOVE it in both the turquoise and the bottle green.

This sequin top from Frame is so cool. I love that it takes a classic French tee design and levels it up with sequins.

A faux fur coat is the ultimate in overdressing, mainly when it’s over the top like this one. I find fuzzy coats very sexy and empowering, don’t you?

Or, on another note, how about this? Pink tulle is frothy and fabulous, non?

These Manolo booties have a “holding court” vibe, particularly in royal red, while a velvet leopard platform like this takes any look from meh to major league when worn with a sock or tight.

Or this mule with jeans and a tuxedo jacket - where understated and overstated can converge. Think of Jenna Lyons, a master of overdressed yet underdressed chic. Like the jeans she wore to the RHONY reunion with a tux jacket, sheer top, and black tie. Scandalous for not being a gown but very, very chic.

Or a sequined blazer with a casual pair of pants and a beautiful shoe—a lovely mix, wouldn’t you agree? I immensely like the mix of dressed-up glam with dressed-down comfort. When I think of overdressing, my mind goes somewhere corseted and uncomfortable, but this proves you can be a bit more done up but also laid back.

At the end of the week, we’ll chat about underdressing, which, to be fair, is far more my cup of Kombucha, though I may be considering after researching this piece. And, of course, it’s all about how you put it together. It’s deliberate, intentional, and delightfully over the top.

After all, shining bright like a diamond whenever one wants seems like a great idea. Dress for the life you want. XO