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. Whilst 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 this 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 shape of the shoe made her legs look like they go on and on (and on), whilst 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 added a V-neck waistcoat, delicate jewels and a pair of tinted brown aviators, crafting an elegant outfit that would easily see you through the season. Dare I say, it’s the perfect September ensemble: streamlined, easy and inherently chic.
Not the first time we've seen her step out in this inherently elegant formula, it's safe to say that the pairing looks just as chic now as it did in 1999.
Below, shop the best black trousers and pointed-toe heels to re-create Aniston’s outfit 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 one of my most-worn pairs of 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 its elevated basics.
Style with the matching blazer or pair with a simple tee.
Shop the matching Emily Scoop V Neck Waisted Blazer (£175).
The slingback design adds a sleek point of interest as well as some light support.
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