September X, 2025
Top TOMS shoes for Fall-Winter 2025
When the first leaves start to fall and the temperature drops, one question comes to mind: which shoes will carry me through the season while keeping me stylish?
Cosy layers and bold textures are ideal for the autumn and winter season, but no outfit is complete without the perfect pair of shoes. From city streets to weekend getaways, what you wear is setting the tone for your whole look.
The ideal fall-winter shoes should be warm enough for the chilly days, stylish enough to elevate your outfits and versatile enough to fit both casual and dressed-up moments. TOMS makes it easy for you to find the perfect pair to feel great, look great and keep up with whatever the colder seasons brings your way.
Rylie boot
Are ankle boots in style in 2025? The answer is yes!
Rylie is a bold ankle boot crafted in rich suede with a stacked leather-wrapped heel. It’s available in a striking leopard print and it's a versatile silhouette that represents a perfect blend of comfort and personality. Leopard print is making a statement this season, and the Rylie fits seamlessly into this trend. With a slip-on design that makes it easy to wear, Rylie is the perfect mix of all-day comfort and style - one of the best dress casual boots for women this season.
Styling Tip:
For an everyday look, you can pair them with black denim trousers and a striped knit, or dress them up with a leather skirt and neutral accessories for a bolder statement.
Bennet
The Bennet is a modern boot crafted with water-resistant nubuck leather uppers, designed to handle the weather while keeping your look sharp. The dual side gores make it easy to slip on and off, while the stacked leather-wrapped heel adds an elegant finish. Sleek, minimalist boots for office for women are a must have this fall, and Bennet fits perfectly in this category. Practical. Durable. Effortlessly elegant.
Styling Tip:
For an off-duty vibe, style them with cosy socks peeking out under straight-leg trousers and a comfy knit. If you’re going for a more balanced mix of feminine and utilitarian, the Bennet is the ideal boot to wear with dresses and skirts, and by adding a relaxed knit paired with neutral accessories - you have the perfect outfit.
Carlo Mid Terrain 2.0
The Carlo is crafted of oak brown water-resistant leather, perfect for rainy days in the cold season. With an elegant touch Carlo becomes the must-have for this autumn-winter season. This versatile model transitions effortlessly from the office to after-work plans. Whether you’re heading out with your friends or dressing up for a holiday celebration, Carlo adds just the right touch of elegance to keep your look sharp and refined.
Styling Tip:
The Carlo Mid Terrain can be styled with rolled-up trousers to obtain a clean silhouette or wear them with tailored chinos and a crisp jacket for a more refined yet laid-back look.
Millie
Every girl's dream is to be comfortable and stylish during the colder season when the rainy days challenge your wardrobe. Meet Millie, your new wedge-style platform Chelsea boot to wear all season long. Millie is perfect for adding that stylish height to any look with durable water-resistant leather uppers and a lightweight sawtooth rubber outsole. The boot also has cosy knit gore and collar details that adds a warm and cosy vibe to any outfit. With Millie, it’s easy to hop on any trend this season.
Styling Tip:
For a black-on-black look you can style the boot with black tights, a leather skirt and accessories to your liking. For a more casual outfit, the Oak Brown Nubuck Leather Millie makes a great pair of lightweight boots for work or leisure when styled with a pop of colour.
Cara
Loafers have always been a staple item in every wardrobe, striking the balance between timeless sophistication and everyday wearability. Meet the Cara, our loafer that features perfectly chunky lugged soles and sleek leather uppers, with some of our pairs featuring tassels and basket-woven texture. With CloudBound™ insoles, this go-with-anything style is both comfortable and supportive. If quiet luxury is your go-to trend this season, Cara is the perfect loafer for you.
Styling Tip:
Cara elevates any business casual outfit – paired with a classic pair of blue jeans and a leopard print shirt strikes the perfect balance between polished sophistication and a bold personality.
Griffin
Griffin is one of the best boots for men this season. In the Griffin Chelsea boot you’re ready to tackle any kind of weather this season is going to throw at you. From pouring rain to snow, these boots are going to become an autumn-winter essential. Made of water-resistant walnut brown leather with cushy CloudBound™ insoles, Griffin keeps you comfortable and confident all day. These boots elevate every outfit, giving it a touch of elegance and sophistication.
Styling Tip:
The best way to style these boots is with neutral and earthy tones that balance the look and keep the elegant vibe of the boot. With Griffin, no matter what kind of event you attend, step in with confidence.
Carolina Mary Jane
The Carolina Mary Jane represents a timeless silhouette with a playful twist that blends modern ease with the classic charm. This espadrille features the rope-wrapped platform of our signature Carolina, while the new feminine Mary Jane strap and rounded toe make this style feel both chic and versatile.
Styling Tip:
Perfect for pairing with anything from wide-leg trousers to fit-or-flare dresses / skirts and a cosy knit, Carolina Mary Jane is ready to take you from casual afternoons to dressed-up evenings effortlessly.
Astrid
The Astrid boot brings a mix of utility and sophistication to the table. Its durable lug sole and lightweight design with extra details such as the soft suede upper, cosy faux fur shearling gore and decorative strap with hardware details, Astrid represents everyday practicality with a classic, polished touch. Perfect for rain too, this boot is treated with Defender Repellent® with Scotchgard™ protector to repel water.
Styling Tip:
Perfect for pairing with tailored coats and relaxed knits, Astrid is tapping into the season’s love for functional footwear that doesn’t compromise elegance or style. Whether we’re talking about city walks or weekend getaways, Astrid is the go-to boot for you.
Oslo
From those early crisp mornings to late relaxed evenings, the Oslo slipper is your go-to for comfort. With faux-fur lining and textured herringbone, Oslo creates a perfect blend of coziness and sophistication.
Styling Tip:
Pair the Oslo with your favourite loungewear set or soft joggers for a chic at-home look. Throw in a cardigan or oversized knit and now you’re ready to tackle both slow mornings and quick errands in effortless comfort.
Best boots per occasion:
- Day to Night – Millie: Super versatile because of its medium height heel. Dress it up or down, from office to after work drinks.
- Errands – Bennet: Slip into them easily for a quick run to the grocery store on the corner.
- Winter Walks – Wylder: Stay warm and dry with water-resistant nubuck, faux-fur lining, adjustable laces, and a lug sole for extra grip on muddy roads.
- Office attire – Rylie: Elegant suede ankle boot with a leopard accent, heel zip, and CloudBound™ insoles. Perfect for office comfort.
- Night out – Evelyn: Fashion meets function with a padded sole, block heel, and easy zip, makes it the perfect boot for a night out.
Tips for Choosing the perfect pair for this Fall-Winter season
The fall and winter seasons are all about embracing the cosiness, the crisp air, and having the right shoes that will carry you through it all. TOMS offers designs that blend comfort, durability and a timeless style. With TOMS you’ll never have to choose between practicality and personality.
Here are some tips to keep in mind when choosing the perfect pair of shoes for the cold season:
- Weather-proofing: Opting for water-resistant or water-repellent leathers, or durable materials are a must, your shoes should be able to handle the rain, snow and slush.
- All day comfort: TOMS CloudBound™ cushioned insoles keep you comfortable from morning to evening.
- Seasonal versatility: Choosing versatile styles is a must. From casual days to dressed-up events, you should be able to step in confidently anywhere.
- Trend meets timeless: This season is all about bold prints, textures or classic details that stay stylish year after year.
- Warm details: Features such as linings, knit gores, faux fur or thicker soles will keep you protected against the chill.
The only question left is: where will your TOMS take you this fall and winter season?
Explore the collection now and find your perfect pair!
Shoes for everyone and every day, that give back with every purchase.
FAQ
1. Are TOMS boots waterproof?
Most TOMS boots are water-resistant or water-repellent, rather than fully waterproof. This means that our boots are designed to handle light rain or snow and damp conditions. However, they’re not built for heavy rain and deep snow.
2. What are the best boots for the office?
The best boots for the office should be comfortable, well polished and versatile. TOMS offers multiple options such us: Bennet for women, Griffin for men, Millie for women etc.
3. How do you style ankle boots?
Ankle boots are perfect for pairing with rolled-up jeans or jeans with a cropped cut. Styles like Astrid are versatile enough to work with skinny, straight-leg, wide-leg jeans or even long flowy skirts.
4. What winter boots are in fashion for 2025?
If this season would be described in 3 words, it would be cosy-meets-polished. Leopard print and leather boots with chunky lug soles are landing the trends. Colours like black, brown, beige and patterns like leopard print are a staple this season. TOMS styles like Rylie, Millie, Bennet and Astrid combine the comfort and style, making them some of the best winter boots for women.
5. Can leather boots be stretched?
Yes, leather boots can be stretched because leather is a pliable, natural material that can expand to fit your feet more comfortably. You can stretch the leather boots by wearing them with thick socks or using a boot stretcher tool.
