Cold Weather, New Energy
Boot season is doing something interesting this fall and winter: instead of asking you to rebuild your wardrobe, the strongest styles are making what you already own feel entirely different.
The Brands Driving the Conversation
Steve Madden is showing up with real momentum this cycle. Model Azzy Milan has been front and center in the brand’s fall campaign, giving its boots a visual identity that skews younger and more editorial than the label’s mass-market reputation might suggest. It’s a deliberate positioning move – Steve Madden wants to compete not just on price, but on cultural relevance, and using a model with Azzy Milan’s following is one direct way to do that.
Marc Jacobs is also part of this fall’s boot conversation, bringing the label’s signature mix of nostalgia and deliberate excess to the season. Marc Jacobs has long treated footwear as an extension of a larger aesthetic argument rather than a standalone category, and this fall continues that logic. The boots read as complete statements rather than finishing touches, which means they work best when the rest of the outfit steps back.
Then there is Vivaia, the brand that built its identity around comfort-forward footwear and has continued to attract celebrity attention as a result. Katie Holmes was spotted in Vivaia this season, a co-sign that carries weight precisely because Holmes has become associated with a very specific kind of effortless, low-noise personal style. When someone with her public image chooses a brand, it tends to signal that the product is doing something functional – not just aesthetic.
What connects Steve Madden, Marc Jacobs, and Vivaia is not a shared design language – they occupy completely different points on the market spectrum. What connects them is timing. Each brand is putting boots at the center of its fall and winter storytelling at the same moment, which collectively reinforces the category’s dominance for the season.
What These Boots Actually Do for a Wardrobe
The promise at the center of this fall’s boot trend is specific: the right pair can make an entire wardrobe feel new. That’s a strong claim, but it holds up when you look at how boots function differently from other footwear categories. A new pair of boots changes the silhouette of trousers, the proportion of skirts, and the overall weight of a look in ways that sandals or sneakers simply don’t. The shaft height alone – whether it hits the ankle, the calf, or the knee – can shift the visual balance of a full outfit.
Knee-high and over-the-knee styles tend to do the heaviest lifting in this context. They visually lengthen the leg when worn with skirts or dresses, and they add structure to otherwise casual combinations like straight-leg jeans and a relaxed knit. The brands featured this season are leaning into that structural quality rather than fighting it.
Ankle boots are playing a different role. They’re more versatile entry points – lower commitment, easier to style across a wider range of temperatures and occasions. Steve Madden has historically been strong in this format, and this fall is no exception. The ankle boot remains the most practical way to test a new silhouette or finish without overhauling anything else.
Katie Holmes in Vivaia is an illustration of that practicality in action. The brand’s approach to boot design prioritizes wearability – cushioning, sustainable materials, a fit that holds up across a full day – and Holmes’s public appearances tend to reflect exactly that kind of real-world functionality. She’s not styled for a runway; she’s styled for an actual life, which makes the Vivaia association feel consistent rather than forced.
Marc Jacobs occupies the opposite end of that spectrum. Where Vivaia is building a case for boots as everyday infrastructure, Marc Jacobs is making the case for boots as the whole point. The silhouettes coming from the brand this fall are bold enough to anchor an outfit on their own, which requires a different approach to dressing – one where everything else functions as context for the shoe rather than the other way around. That’s a more demanding way to get dressed, but for the right person, it’s also a more satisfying one.
Material choices across the season are running the full range: leather, suede, and weather-resistant fabrics are all showing up in significant numbers. Suede in particular is having a strong moment, which is worth noting because it’s a material that requires more care and signals a slightly more considered approach to dressing. Brands leaning into suede this fall are implicitly betting that their customers are willing to treat footwear as an investment rather than a disposable purchase.
Celebrity Styling as Product Direction
The Azzy Milan and Katie Holmes placements are doing more than generating press. When a brand puts a specific face in a specific shoe, it’s communicating who the product is for and how it’s meant to be worn. Azzy Milan in Steve Madden reads differently than a fashion week street style image would – it brings the brand into a younger, more social-media-native context without abandoning its core accessibility. Katie Holmes in Vivaia reinforces the idea that the brand’s comfort positioning is not a concession but a feature.
The brands active in fall and winter boots this season – Steve Madden, Marc Jacobs, Vivaia – are targeting different customers with different price points and different aesthetic promises. Steve Madden’s price accessibility makes it a volume play; Marc Jacobs is working in a higher register where individual pieces carry more weight and margin; Vivaia is carving out a distinct lane around sustainability and wearability. Three brands, three strategies, one season – and all of them betting that boots are where attention is.
