The Weekend Read✨Stepping into Winter: The Ultimate Guide to Boots for Every Woman

Jenny Goldsmith | Read in 10 minutes

Hello!

The air has definitely turned crisp and the mornings are carrying that tell-tale chill that find most of us already reaching to the back of the wardrobe for our familiar favourite footwear; our boots.

Whether they’re buttery leather knee-highs or well-loved ankle boots, there’s something deeply satisfying about the boot season. It marks the shift from summer’s ease to autumn’s structure; a time to layer, to rediscover texture and to walk with purpose.

Boots are not just a practical necessity, they’re a cornerstone of our personal style. They can ground our outfit, elevate our silhouette and express our personality with every step.

In this Weekend Read, we’ll explore the fascinating history of the boot, the key styles for the Autumn/Winter 2025/2026 season, how to find the best fit for your shape and colouring and how you can wear them with confidence all season long.

A Brief History of the Boot

Boots have been part of our outfits for over 3,000 years. The earliest versions of the boot were purely practical, animal hides wrapped around feet and legs for protection against cold and rough terrain. But as civilisation evolved, so did craftsmanship.

By the 17th century, boots had become a symbol of status and style, from the polished riding boots of the aristocracy to the sturdy workwear of farmers and soldiers.

Women’s boots, however, only came into prominence in the 19th century, when modesty and fashion converged. Lace-up ankle boots became an essential part of Victorian dress, offering both decorum and independence, the first glimpse of footwear designed for movement and purpose.

Fast forward through the 20th century and boots have mirrored women’s evolving roles and freedoms. The go-go boot of the 1960s, bright white, patent, and unapologetically bold, reflected liberation and youth. The 1980s gave us rebellious Doc Martens, while the sleek stiletto knee-highs of the 2000s exuded glamour and power.

Today, boots continue to evolve, balancing comfort, sustainability and of course individual expression like never before.

The Weekend Read✨Stepping into Winter: The Ultimate Guide to Boots for Every Woman

Know Your Boots: The Styles That Shape Your Wardrobe

Boots come in countless shapes and finishes, but a few key styles form the backbone of every great wardrobe.

Ankle Boots: These are a modern classic. They're perfect with jeans, midi skirts or dresses, ankle boots bridge casual and smart effortlessly. Look for sleek leather for a polished feel or suede chunky soles for an edgier, youthful twist.
Chelsea Boots: These are instantly recognisable by their elastic sides, Chelsea's are timeless and versatile. You can pair them with cropped trousers for work, or wear them off-duty with denim and a jumper.
Knee-High Boots: These are elegant and elongating, working beautifully with skirts, dresses and tucked-in jeans. They can balance proportions and add polish to simple outfits.
Over-the-Knee Boots: What were once a daring boot are now a stylish staple. Ideal for taller women or those who love a statement look. You can wear with them short skirts or skorts and opaque tights, or layer over skinny trousers.
Combat and Hiking Boots: These add toughness to feminine pieces and make great all-weather companions with comfort and attitude combined.
Western or Cowboy Boots: These are a big trend resurgence for 2025, often in suede, embroidered leather or tonal stitching. You can style them with floaty dresses or slim jeans for a modern boho edge.
Heeled vs. Flat: A heeled boot will lengthen the leg line and will add polish, while flat styles offer you all-day comfort. The key is choosing what supports your lifestyle and you the best.

Autumn/Winter 2025 Boot Trends

This season, designers are reimagining classics with tactile textures and soft structure. Look out for:

Mid-Calf Magic: This is a flattering length that works with wide-leg trousers or midi skirts.
Block Heels: These are more wearable and comfortable than stilettos but are still elegant as they strike the perfect smart-casual balance.
Textured Leathers: Why not try a croc-effect, brushed suede or glossy patents which will add depth to simple silhouettes.
Colour Play: Why not skip black this season and try rich chocolate, burgundy, forest green and navy as they now lead the way in the style stakes. For those of you who love a bold statement, ivory and metallic boots offer modern polish.
Sustainability: You can expect to see more recycled leathers, eco-suedes and repair-friendly designs from brands like Vivaia, DuoBoots, Clarks, Boden and Russell & Bromley.

The key to investing wisely this season? Choose boots that harmonise with your wardrobe palette and lifestyle, not just what’s trending on social media.

Colour Confidence: Beyond the Black Boot

For many women, black boots are the default. They’re versatile, safe and easy to match. But in reality, black isn’t always the most flattering or versatile option. The right boot colour will harmonise with the colours of your outfit choice in your seasonal colours, instead of working against it. A great coloured boot will instantly update your look.

Here’s how to think beyond black:

Brown and Tan: These are warm, inviting tones that pair beautifully with the autumn and spring palettes. Pair these with reds, aquas and greens for a modern look.
Navy and Charcoal: These are cool, sophisticated alternatives to black, ideal for Winters and Summers (Autumns and Springs can wear a warmer navy). Try pairing navy or charcoal boots with your grey, pinks, or this seasons must have burgundy pieces for sophistication.
Oxblood and Burgundy: These tones are deep and luxurious, shades which flatter the cooler complexions and bring out a hint of drama.
Cream & Ivory: These shades are unexpected for this time of year but offer a modern, stylish edge. You can pair them with the neutrals from your season.
Metallics: Gold and silver boots are a real style statement for A/W 25/26. Stylish and striking, the metallic boot is the hot trend this season and will work as a great neutral in your wardrobe.

When choosing boot colours, consider your clothing palette as well as your colour season. Warm-toned wardrobes pair best with gold hardware and tan or chocolate leathers, while cool wardrobes shine with silver hardware and grey or cool navy leathers. Think of your boots as part of your outfit’s colour story, not just its foundation.

Styling Boots for Every Occasion

One of the joys of the boot season is how adaptable they are. The right pair will take you from the school run to your office meeting, from shopping to evening drinks, all with a simple change of outfit.

For work, opt for sleek ankle boots with tailored trousers or a midi dress. A low block heel adds confidence and comfort. For casual days, flat knee-highs or Chelsea's with jeans and a chunky knit always feel timeless. You can add a long coat for effortless chic. For evenings, try a heeled ankle boot with a dress or leather-look skirt. Metallic or patent finishes will add instant polish. Finally, for weekends and outdoors, wear waterproof leather or lined walking boots to keep you practical and stylish.

House of Colour clients might also enjoy pairing boot styles with their style personality: Dramatics might lean into over the knee patent heels or pointed toes. Classics will lean toward timeless, clean lines while Naturals will go for texture with comfort. Gamines will look for the edge with a DM or Chelsea boot, while Ingenues will look for detailing in their boots like intricate stitching or scallops and ruffles in the material. Romantics will opt for soft suedes, heels and sparkly embellishments.

Fit, Shape and Comfort: Finding Your Perfect Pair

The most beautiful boots in the world won’t make you feel good if they pinch, slip or gape. Comfort is elegance and understanding your foot and calf shape is key to finding the right fit.

For Narrow Feet: Seek out lace-up or buckle styles that allow adjustment. Pointed or almond toes can help balance your proportions. Brands like Dune, Boden and Hobbs often cater well here.

For Wide Feet: Choose rounded or square toes, supportive insoles and soft leathers that mould to your shape. Look for wide-fit ranges from Clarks, FitFlop, Hotter, New Look, Next or M&S Wide Fit.

For Wide Calves: Stretch panels, elastic inserts, or adjustable backs offer comfort and a sleek silhouette. Brands like DuoBoots, Sargasso and Grey and Ted & Muffy are specialists in calf-fit options. Also try Gabor, Vivaia, Pavers, Evans or Simply Be and Very for EEE+ fittings

For Petite Calves or Slim Legs: Look for tailored fits or styles that sit just below the knee. Mid-calf and ankle boots often flatter petites beautifully. Avoid excess gaping at the top of the boot for a polished line. Try Whistles, Jones The Bootmaker, Slimcalfboots.com, DuoBoots, M&S and Boden.

For Those Avoiding Heels or Needing Extra Support: Block heels, platform soles or wedge styles give height without strain. Cushioned insoles, arch support and flexible soles are a must, especially for those with plantar fasciitis or sensitive feet.

When trying on boots, wear the socks or tights you’d normally pair with them and check proportions in a full-length mirror. The boot should complement your leg line and outfit, not overwhelm it.

Caring for Your Boots

A little care goes a long way. Regularly clean and condition leather with a nourishing cream and brush suede with a soft suede brush to remove dirt. Apply a waterproof spray before wearing them in wet weather and always dry boots away from direct heat.

Store tall boots with inserts or rolled magazines inside to keep their shape and invest in a cobbler’s quick re-heel when needed, it will give your boots a few extra years. Sustainability starts with looking after what we already own and a well-cared-for boot will last you much longer.

Final Thoughts: Step Into Confidence

Your perfect boots aren’t just about fashion, they’re about how you feel. The right pair supports your stride, enhances your wardrobe and expresses your individuality. Whether you’re striding through the office, walking the dog or heading out to dinner, your boots should move with you in comfort, confidence and colour harmony.

So, as you reach for your favourites (or shop for new ones), take a moment to consider what truly works for your colour palette, proportions and lifestyle. This season, step into boots that make you feel entirely yourself; stylish, comfortable and ready for whatever the autumn/winter season brings.

Next week in The Weekend Read we are talking about the wonderful world of texture and how can you incorporate texture into your wardrobe. Until then, enjoy your cuppa and your The Weekend Read and be sure to share it with your family and friends.

Best wishes,

Jenny & Judi xx

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