Craving - A Ladylike Look

Embracing a more feminine silhouette after years of oversized everything

Feb 21, 2025

For years, I’ve channelled a more masculine look of oversized blazers, relaxed trousers and chunky loafers. However, I’m noticing a shift towards a more feminine silhouette, and I’m fully ready to embrace it.

Recent images of Kendall Jenner and Hailey Bieber leaving an LA restaurant in sheer tights, fitted blazers, and miniskirts (styled by celebrity stylist Dani Michelle) got me excited to try a new look.

A ladylike dressing masterclass from Kendall Jenner and Hailey Bieber

I’ll still be reaching for my oversized pieces, but it’s nice to have some fresh ideas, especially for evening looks which can often be the most challenging to dress for. I bought this Birrot set before Christmas because I loved the waisted blazer. It’s been my go-to for work dinners and events—my equivalent of a little black dress.

You can get a similar style at Aligne (wearing a UK10) teamed with Vintage Chanel via Reluxe and Chanel Slingbacks.

Playing around in my wardrobe to recreate that ladylike look that I’m craving right now. I think the key element for me is going all in. Usually, I balance out my looks with a mix of big/slim silhouettes or toning down feminine pieces with a masculine element, but for a ladylike outfit, I’ll be going head-to-toe and embracing a more sophisticated look.

Blazer Frankie Shop (XS) | Bag The Row | Shoes Chanel

To elevate your wardrobe towards a more ladylike look, think waisted blazers, mini skirts or dresses, sheer tights, simple pumps and top-handle bags.

The Blazer, a wool-blend waisted blazer to pair with a mini skirt
The Mini Dress, a high-neck mini dress with a tailored waist
The Top-Handle Bag, a Savette pochette suede tote, is the ultimate ladylike accessory
The Tights, Wolford 10 denier sheer matt tights
The Dress, a sleeveless, chic, black midi dress

Calvin Klein Collection

The recent Calvin Klein runway show nodded to 90s tailoring, featuring knee-length pencil skirts and collarless jackets, and had an overall refreshing, sharper silhouette.

Carolyn Bessette-Kennedy, who worked for Calvin Klein in the 90s, is my go-to for classic, timeless style inspiration, especially her ladylike evening looks

x4 Outfit Ideas for Ladylike Dressing

Channelling 90s Julia Roberts in Loulou De Saison tailoring + a Savette Bag

Top | Trousers | Earrings | Belt | Bag | Lipstick | Shoes

A fitted top and a mini skirt with sheer tights, I love this colour palette

Top | Skirt | Tights | Ring | Hairspray | Shoes | Bag

A nod to Carolyn Bessette Kennedy’s chic, timeless evening style in a Malina Jacket + Skirt

Jacket | Skirt | Shoes | Bag | Earrings | Blush | Hairband

A classic look in a Malina mini dress + Arket heels

Dress | Shoes | Tights | Perfume | Ear Cuff | Glasses | Bag

The Ladylike Edit

If you’re not ready to fully embrace a head-to-toe ladylike look, you can add elements to your outfit with accessories. A piece of elegant jewellery, a top-handle bag, or a sleek shoe could just be what you need to elevate your outfit.