Lately, I have noticed a serious shift. It’s like there’s something in the air, and it isn’t just a change in temperature. Over the last few years, fashion has generally been divided into two camps: the classicists and the experimental dressers.
The classicists were early adopters of quiet luxury. They pine for Phoebe Philo-era Celine, wear a uniform of The Row-inspired timeless, textured pieces in a monochromatic palette, and have an Instagram algorithm that pushes Rosie Huntington-Whitely and Sofia Richie over all else.
On the other hand, the more experimental dressers are likely to shop secondhand, adopt a TikTok “core” trend, or be Y2K-obsessed. This crowd might cite Alexa Chung as their best-dressed celeb and tell themselves they’re “so Julia” when getting ready in the morning.
But for the first time, there’s a trend that I think will appeal to both parties. It blends the timeless elegance of the quiet luxury camp with the vintage appeal of the experimental group. Enter: **Demure Dressing**.
### What is Demure Dressing?
If you’re not familiar, stay with me. Not to be confused with the “very demure, very mindful” viral TikTok meme by Jools Lebron from 2024, demure dressing is a term we’ve coined for the sudden surge in channeling prim and proper styles reminiscent of the ’50s or ’90s.
Think skirt suits over trousers—maybe with a mini skirt, but also those with a knee-length finish. The blazers are often collarless, have a curved silhouette that cinches in the waist, or can be styled with a belt to achieve the same effect. This approach to tailoring is a totally different vibe from the ’80s power suits that have dominated the last decade.
Worn with low denier tights, slingbacks, polo necks, and pearls, this style was famously adorned by the Kennedys—Jackie Kennedy-Onassis in the ’50s and ’60s, as well as Carolyn Bessette-Kennedy in the ’90s.
### The New York Inspiration
I first realized this trend was about to be huge during a recent trip to New York. Many women on their way to work were dressed exactly like this: full-length double-breasted wool coats with a little structure in the shoulders, worn unbuttoned and dramatically flying open with every breeze. Oversized clutch bags and top-handle “Lady” bags were draped on their forearms, complemented with long leather gloves.
And then I saw not one, not two, but **three pillbox hats** perched purposefully yet effortlessly on neatly combed hair.
This trend is also all over the spring/summer 2026 runways and my Instagram feed. Content creators like Christie Tyler, The Pouf, and Marilyn NK have been early adopters of demure dressing, while designers like Fendi, Gucci, and Calvin Klein showcased collections next spring with the same aesthetic.
### How Does It Compare to Recent Trends?
If you loved the “Frazzled English Woman” era inspired by Miu Miu’s autumn/winter 2023 collection, I think you’ll enjoy this trend too. Similar in style but a little more “put together,” demure dressing feels like a progression from the preppy, playful Miu Miu schoolgirl aesthetic, yet it still retains a sense of irony and fun.
It feels professional and purposeful, yet surprisingly quite sexy and cool.
### Styling Tips
If you don’t want it to feel too “lady-like” and conservative, here are a couple of suggestions:
– Opt for a two-piece with a mini skirt, styled with knee-high socks or low denier tights.
– Choose a knee-length skirt but wear it with a cardigan buttoned only once or twice, showing a little skin on the chest and at the waist.
Whether you want to channel the timeless elegance of *Mad Men’s* Betty Draper or *The Parent Trap’s* Meredith Blake, just know this trend is about to be huge.
—
## 5 Items You Need to Get the ‘Demure Dressing’ Look
### 1. Collarless Blazer
**Style Notes:**
When it comes to conquering demure dressing, the collarless blazer is doing the heavy lifting. I might be biased as I wore one on my wedding day, but there’s something about the lack of lapel that makes this streamlined silhouette simply so chic. Wear it buttoned up as a top (especially great with statement earrings), or layered over a polo neck for extra warmth.
**[Shop Collarless Blazers]**
### 2. Pillbox Hat
**Style Notes:**
During my recent New York trip, the pillbox hat was the signature finish that made the best-dressed women really stand out. It’s not so much about practicality for warmth, but more about adding a sophisticated finishing touch. Pair it with pearl jewellery and a high neck to nail the look.
**[Shop Pillbox Hats]**
### 3. Knee-Length Skirt
**Style Notes:**
Hang up the minis, and put away the midi and maxi skirts—for now, it’s all about knee-length. In summer, sheer versions with a straight silhouette were popular, and this season you can definitely rewear these with low denier or white tights. I suggest a two-piece with a matching jacket in wool, linen, or cotton, in black, beige, or grey for versatility. Check, tweed, or gingham patterns also hit the mark.
**[Shop Knee-Length Skirts]**
### 4. Top Handle Bag
**Style Notes:**
Top handle bags might be less comfortable to carry, but they are a core accessory to the demure dressing trend. Because every ‘ladylike’ dresser needs a classic ‘Lady’ style bag! This timeless piece works for both evening and daytime occasions (as long as you don’t need to carry a laptop). If you want to invest in a luxury one, nobody does it better than Jil Sander or Mansur Gavriel.
**[Shop Top Handle Bags]**
### 5. Slingback Kitten Heels
**Style Notes:**
Writing this piece made me think about the crossover styles from the ’50s and ’90s—two culturally opposing decades. Yet both shared the slingback silhouette: deliciously pointed, square-toed shoes with a small heel, whether kitten height or a thicker block. Nothing feels more poised and proper than slingback kitten heels.
**[Shop Slingback Shoes]**
**[Shop More ‘Demure’ Items]**
—
Demure dressing is shaping up to be one of the most exciting trends to watch. Whether you’re a quiet luxury classicist or an experimental fashion lover, this style offers a perfect blend of timeless elegance and vintage charm.
Start building your capsule wardrobe now to embrace this poised, polished, and effortlessly chic trend.
https://www.whowhatwear.com/fashion/trends/demure-winter-fashion-trend
