I've always felt that September shifts the styling mood more than any other month. As the new-season energy kicks in, capsule wardrobes often follow suit, mine included. Without even meaning to, I’ve been trading in jeans for tailored trousers, tees for button-downs and trainers for something sleeker as I work towards channelling a more polished silhouette.
While easing into this new rhythm, I’ve been on the lookout for styling inspiration to maximise my early-autumn looks. And this morning, Jennifer Aniston delivered in spades, stepping out in an autumn shoe trend that elevates tailored trousers, in a '90s-minimalist kind of way.
Styling her long black tailored trousers with pointed-toe heels in glossy black leather, the pointed-toe made it look like her legs go on and on (and on), while the sleek heel added a certain poise that flats can never quite match. A reliable pairing that felt sharp and polished, but not overly serious, Aniston layered a V-neck vest, delicate jewels and a pair of tinted brown aviators, crafting an elegant outfit that easily sees you through the season.
Dare I say, it’s the perfect September ensemble—streamlined, easy and inherently chic. Below, shop the best black trousers and pointed-toe heels to re-create Aniston’s formula below.
Shop Pointed-Toe Heels and Black Trousers
These come in UK sizes 6—24.
Style with sleek black trousers or pair with your favourite jeans.
Be quick! These are on their way to selling out.
Every great wardrobe starts with a classic black heel.
I have these myself, and they're some of my most-worn trousers.
The suede finish gives these a luxurious edge.
These also come in a deep shade of brown.
I'll always come back to The Row for their elevated basics.
Style with the matching blazer or pair with a simple tee.
The slingback design adds a sleek point of interest as well as some light support.
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