4 Easy Winter Shoe and Boot Styles I'll Wear With Every Outfit This Season

There is no time of year I love more than autumn. After months of wearing as little as possible to manage the heat, I thrive in the season where there's an excuse for more—layers of knits, coats and scarves, and of course, the footwear to match. Shearling, Chelsea, hiking, knee-high or ankle, I'm a big lover of boots. The timelessness of classic winter boot styles means I have as much excitement in taking them out of storage in preparation for the colder months as the day I bought them. And these days it's not just boots—there are sneakers, wellies and stylish leather flats like mules or loafers to keep our feet well-heeled and warm. 

Working in fashion, one of the things I'm asked about most at this time of year is the footwear brands that can not only withstand the elements, but are also comfortable, affordable and stylish. Each time I give the same response: FitFlop. The brand already has a solid reputation for quality; backed with extensive research, each style (be it sandal, sneaker or boot) has been bio-mechanically engineered to give the best possible support, and is designed to work with your body's alignment and natural movement.

Okay, so we know FitFlop's latest collection is 100% practicality-approved, but is it fashion-editor approved? I can say with certainty that it is. I put some styles to the test, creating four classic, casual outfits that I will wear on repeat this season, styled around my favourite pairs of shoes and boots from the A/W 23 collection.

I love to walk, especially in autumn and winter, and I have a dog so I spend many of my weekends on long strolls with her around London, as well as where my parents live in the Cotswolds. When I have time, I also love to walk part of my commute into the office during the week. This means I need stylish footwear that can manage my step count. When making my selection for these looks, I had all of this in mind—I wanted fashion-forward outfits for the office and pared-back options for grabbing a coffee in the park. In light of this, I chose boots and shoes from FitFlop that speak to some of the season's most popular trends, as well as others that felt a little more classic. Take a stroll with me below to discover them all. 

Shearling boots are back. We're certainly aware of the return of Y2K fashion by now, but we've also noticed more shearling boots on the fashion set than ever before. And why not? They're comfortable and cosy, and with their extra-thick, chunky sole, they also have a contemporary aesthetic. Also check out the double-faced shearling, which is hide on one side and this super soft fluff on the other. Personally, I love this style of boot with a super-low height that barely grazes the ankle, and if you scroll Instagram for just a minute, you'll see editors and influencers alike wearing them with straight-leg jeans and an oversized blazer, like I've done here. 

These Gen-FF Shearling Boots also come in black, but I love this signature tan shade, which I think looks great with denim. If you do opt for the black pair though, I'd go monochrome and style them with black dresses or leggings. So simple and yet so effective, if it gets a little chilly, just add a scarf to complete this look. 

Quiet luxury has been the fashion phrase of 2023. Online searches for "How to look rich" have risen dramatically as we look to classic outfit ideas that elevate our style persona. One easy way I like to do this is by dressing in one colour (or tones of it) head to toe. Monochromatic dressing is most effective in neutral hues, and whilst going all-black is easy and effective, I love to take it up a notch with tones of cream and beige, accessorising with gold jewellery.

The icing on the cake of the look I've created here is of course, the leather mules. Sophisticated, sleek and oh-so comfortable, they're perfect for anyone with minimalist taste. They're ideal for work with tailored trousers and a cosy knit for a classic yet cool look, and whilst I love the cream colourway to add to my tonal theme, the tan and black options are also very tempting. 

Newsflash: Not all boots were made for just walking. Take the Neo-D-Hyker that I'm wearing here— although designed with hiking in mind, I would make a case for this sneaker's place on the streets as well as the mountains, country hills and wherever else one chooses to ramble. You may have heard of or seen the "gorpcore" trend manifesting over recent seasons, where utilitarian garments designed for the great outdoors have become a major influence on  streetwear.

We saw this best envisioned at Copenhagen Fashion Week, where Scandi influencers and editors styled hiking boots and shoes with typically feminine dresses. The Neo-D-Hyker does come in boot form, but I love the sneakers I'm wearing here, as I can pair them with a pair of fun socks. To make the look autumn/winter-friendly, I've layered my dress with two of my winter wardrobe staples: a knitted vest and a long trench coat. 

The Chelsea boot is an autumn staple that I think every capsule wardrobe should include. Easy to wear with jeans and midi and maxi hemlines alike, it's great to have boots in your roster that you don't have to think about. A smarter casual option than trainers, they're still comfortable enough that you can just throw them on and go. And what's so great about FitFlop's version is that they're waterproof and leather (clever or what?), which anyone in the UK can appreciate because you're covered against the elements and every weather eventuality. 

The sole is super chunky yet lightweight, so the boots have a modern feel whilst still being a timeless classic. I love to pair mine with mom jeans (because the tapered style shows off the whole boot) and a padded jacket. This is my go-to look for weekend walks in the park with friends that are followed by long, lazy pub lunches. 

Discover more of FitFlop's A/W 23 collection here.