When it comes to timeless style, some shoes effortlessly transcend trends, becoming must-haves that withstand the test of time. In my wardrobe, there are three classic shoes that exude an anti-trend aura, effortlessly elevating any outfit with their versatile charm.
Firstly I'm tackling boots, a quintessential cold-weather essential. I always gravitate towards simple, pared-back silhouettes and neutral palettes to further bolster their wearability. Pair them with a flowing printed dress and knitted layers or with tailoring and the right pair will effortlessly add a touch of laid-back hushed luxury to any look.
Next, we have trainers, a true wardrobe staple. Their versatility knows no bounds, as they seamlessly blend comfort and style. From running errands to weekend outings, they effortlessly pair with jeans, skirts, or even a dress. I've focused my search on cult styles, from Nike Air Force 1s to Converse high-tops to further ensure their timeless appeal. It's a guarantee—these kicks will bestow you with a cool, effortless vibe that never goes out of fashion.
Lastly, let's look at black heeled shoes. These sleek and chic shoes effortlessly transition from day to night. Whether you're heading to the office or a dinner date, their timeless appeal ensures a polished finish to whatever outfit you wear. Look to sleek silhouettes such as mules or Mary Janes and gravitate towards and comfortable heel heights to make them a reliable option for any occasion.
In a world where trends come and go, these classic shoes remain steadfast in their appeal. They embody timeless style and adapt to any outfit or occasion. With these anti-trend staples in my wardrobe, I can confidently navigate the ever-changing fashion landscape, secure in the knowledge that I'm always stepping out in style. Below, I've assembled some of my favourite styles in each category, filled with some gems I found in the Amazon Prime Day 2023 sale we're all currently obsessed with. Because if there's one thing I love more than timelessness, it's a bargain that will stand the test of time.
Scroll on to shop my edit of the best anti-trend shoe styles to invest in, along with the best shoe, boot and trainer deals on during Amazon Prime Day.
SHOP AMAZON PRIME DAY 2023 SHOE, BOOT AND TRAINER DEALS
1. Pared-Back Boots
Pointed-toe silhouettes are having a moment, as are brown hues. However, if you prefer, this classic boot also comes in black.
These look so much more expensive than their price tag thanks to the square toe and chunky heel.
Almond toes always look sleek, especially in a rich suede.
The print may be statement, but the neutral colour palette and simple shape mean these boots are very versatile. There are, however, plain black and tan colour ways to choose from too.
White boots are hard to get right, but the soft ecru tone ensures these knee-highs look chic. Again, should you prefer, they also come in timeless black.
2. Classic Trainers
These are the trainers I always see stylish people wearing in London.
Adidas Gazelles remain incredibly sought after—especially in neutral colours.
Converse high-tops are beloved by all walks of fashion people.
My (and Kate Middleton's) go-to canvas kick.
You heard it here first—Old Skool Vans are back. Though, in my opinion, they never left.
3. Black Heeled Shoes
The asymmetric straps on this pair give them a modern feel.
Tick off two major shoes trends in one with these t-bar Mary Janes.
The flared heel on these sandals not only adds interest, but makes them more stable to walk in.
The quilted and toe-cap detailing feels so French. J'adore!
I challenge you to find an outfit these won't go perfectly with.
Next Up: I'm a Fashion Expert—These Amazon Prime "Big Deal Days" Pieces Will Sell Out First
-
35 Incredibly Chic Finds From All of the Best Presidents' Day Sales Worth ShoppingDon't miss out.
-
I Forgot About These Winter Boots Until Meghan Markle Styled a Pair In the Most 2025 WayGood thing they're on sale.
-
I'm a New Yorker: 5 Chic Items From the Nordstrom Half-Yearly Sale I Already Spotted on Women in SoHoThe West Village too.
-
My 2025 Vibe Is Stealth Wealth: 35 Luxe-Looking Items I'm Eyeing From the Nordstrom Half-Yearly SaleWealth whispers.
-
Missed Cyber Monday? 30 Chic J.Crew, Nordstrom, and Revolve Items That Are Still on SaleWith deals starting at under $20.
-
Wealth Whispers, But I'm Screaming Over These Quiet Luxury Cyber Monday Finds From Nordstrom, J.Crew, and Ralph LaurenThree, two, one, shop!
-
Native New Yorkers and Cool-Girl Transplants Agree on One Thing: These 31 Nordstrom Black Friday Sale Items Are *It*Start the shopping.
-
I Shop for a Living—51 Jaw-Dropping Cyber Monday Deals From My 17 Favorite BrandsThe deals have never been this good.
