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woman smiling while sitting on the sofa in a floral midi dress

How to wear a floral midi dress in your 50s without looking dated

Floral midis are midlife uniform, says Rosie Green

Rosie Green
Second Act columnist
May 25, 2025
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Those pesky fashionistas have been prophesying the floral midi dress' demise for a few years now. Muttering about them being 'over'. Making snide comments about their 'basic' nature. 

I've been ignoring such whisperings because I love them. Floral midi dresses are my dream garment. A single piece of clothing (less washing!) that's easy to throw on.

You can dial up their smartness with heels or make them casual with sandals or trainers. For me, they're flattering because they show off my narrowest part (ribcage) and skim over the fullest (my hips). And, bonus, I only have to shave/tan my legs from the knee down. 

When the trend hit, probably five or so years ago, I welcomed their arrival with trumpets. Rejoiced that the style stars had aligned for me.

Rosie Green smiling on a balcony in a pink floral dress
Rosie Green found her style vibe with midi dresses

And so, I invested heavily. Bought cheap ones from Zara, mid-priced ones from Wyse, expensive ones from Ba&sh and dreamt of Erdem and Valentino. 

At the time, it was a departure from my usual, Kate Moss-inspired style. In my fantasies, I have her wardrobe. Chic, sexy and a little bit rock n roll. Think sheer chiffon blouses, pencil skirts, high heels, patterned tights, leather and suede. And all black. Made edgy with distressed seams and a flash of lingerie. 

But then the arrival of these floral dresses convinced me to do a style 180 and embrace overt femininity. I was happy with my decision. Until last year, when the white trainer/ floral dress combo suddenly felt a bit, whisper it, dated.

Woman laughing in a pink dress while holding a fluffy white dog
Rosie loves a midi-dress

A new wardrobe era

This year, when the weather finally perked up, I looked in my wardrobe, crammed with floral dresses and I did an involuntary sigh. Did I need to do a cull? Take the whole lot to the charity shop? 

I have been mulling over this conundrum for the last few weeks, and I have decided the answer is a resolute no. My finances can't deal with the sudden loss of 80% of my wardrobe.

So, I consulted with my stylist friends, and we concluded that by switching up my accessories/approach, the floral midi can live to see another season. 

Woman sitting on a soft blue sofa wearing a floral midi dress
Rosie shares her advice for wearing midi-dresses

5 style rules for wearing floral dresses in 2025

1. Consider footwear

The most important thing is not to be too 'polite' with the look. Being too conservative (court shoes/blow out, etc) is what makes it look dated.

Try teaming your dress with boots to counterbalance the femininity. Ankle boots in suede have an 'I'm with the band' vibe. Try Isabel Marant's styles if you can afford them (or a copy if you can't). Biker boots also work. 

 Change up your trainers. The plain white ones you had a few years ago? Switch to a chunkier, more sporty style. 

2. Go boho

Embrace boho. If you are buying a new floral dress, take inspiration from the aesthetic at Chloé and Zimmerman. Think ethereal, flouncy, and romantic. 

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3. Think 90s

Look to add elements of 90s style to your floral dress. Sheer fabrics for an edge, or try out a slip shape.

4. Hair styling

Your hair is important here. A little mussed-up hair a la Sienna Miller is good. Newsreader style helmet head? Not so much. 

5. A sexy edge

Lingerie accents make a dress instantly feel sexier. Think lace, silk and spaghetti straps.  

 

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