The Shoe Deals I'm Shopping in Amazon's Prime Day Sale 2023

last updated 10 October 2023

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.

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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

The Drop

Gemini Tall Heeled Boot

Pointed-toe silhouettes are having a moment, as are brown hues. However, if you prefer, this classic boot also comes in black.

The Drop

Ibita High Heel Side Zip Ankle Boot

These look so much more expensive than their price tag thanks to the square toe and chunky heel.

The Drop

Jane High Heel Pull-on Sock Boot

Almond toes always look sleek, especially in a rich suede.

The Drop

Bayonne Tall High Heel Boot

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.

The Drop

Kennedy Pull on Lug Sole Platform Boot

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

Nike

Air Force 1 Trainers

These are the trainers I always see stylish people wearing in London.

Adidas

Gazelle Trainers in Savannah White Glory Red

Adidas Gazelles remain incredibly sought after—especially in neutral colours.

Converse

Chuck Taylor All Star 70 Canvas High-Top Sneakers

Converse high-tops are beloved by all walks of fashion people.

Superga

Coty Canvas Trainers

My (and Kate Middleton's) go-to canvas kick.

Vans

Old Skool Canvas Trainers

You heard it here first—Old Skool Vans are back. Though, in my opinion, they never left.

3. Black Heeled Shoes

The Drop

Amelie Strappy Square Toe Heeled Sandal

The asymmetric straps on this pair give them a modern feel.

Dream Paris

T-Strap Mary Jane Heels

Tick off two major shoes trends in one with these t-bar Mary Janes.

The Drop

Lina Martini Heeled Sandal

The flared heel on these sandals not only adds interest, but makes them more stable to walk in.

The Drop

Paulina Pointed Toe Two-Tone Mule

The quilted and toe-cap detailing feels so French. J'adore!

The Drop

Avery Square Toe Two Strap Heeled Sandal

I challenge you to find an outfit these won't go perfectly with.

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Maxine Eggenberger is Who What Wear UK’s deputy editor and has over thirteen years of experience in fashion journalism. She been creating engaging and elevated style content specifically for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, self-styled shopping stories and columns, including her edit of the best new-in buys. She ensures the highest editorial standards are met across the site, leads the editorial team in their SEO strategy and keyword planning, works closely with the beauty team on content initiatives, represents the brand at industry events, and regularly contributes to social media, including her own Who What Wear UK TikTok franchise, French Style Fridays. Previously, Maxine appeared on ITV's This Morning in her own fashion segment and has interviewed countless celebrities—everyone from Victoria Beckham to Oscar winner Lupita Nyong’o.

Prior to Who What Wear UK, Maxine’s career began when, after completing her first-ever internship at Look magazine, she was offered a position on the brand's fashion desk. She accepted, leaving university a year early in the process. Her passion and natural talent for writing and styling meant she swiftly rose through the ranks to become the title's fashion news and commercial content editor, with a stint as InStyle.co.uk’s fashion and beauty writer along the way. She later served as Look’s acting Editor in Chief, overseeing both print and digital, before embarking on a successful freelance career, working with Grazia, The Pool, and Marie Claire amongst others.

Maxine is based remotely from her countryside home near Edinburgh where she spends her downtime renovating her house, walking her dogs, hosting friends and trying to master the art of making Old Fashioned cocktails.