3 Anti-Trend Shoes I Immediately Added to My Amazon Basket Today

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.


1. Pared-Back Boots

2. Classic Trainers

3. Black Heeled Shoes

Next Up: I'm a Fashion Expert—These Amazon Prime "Big Deal Days" Pieces Will Sell Out First

Maxine Eggenberger
Deputy Editor

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.