Shoes are the foundation of every great outfit, especially as we transition into the cooler months. This season’s fall and winter footwear trends strike that perfect balance between comfort and style—exactly what women over 50 are looking for. And if you invested in a few pairs last year, you’re in luck: many of fall 2024’s standout styles are still going strong, with just a few fresh updates. Whether you’re refreshing your staples or ready to try something new, these six shoe styles are as wearable as they are on-trend.
Fall and Winter Shoes for Women Over 50
Block Heel Booties – Style & Stability in One
A well-made block heel bootie is the go-to shoe of the season—and for good reason. The block heel offers support and all-day comfort, while the sleek silhouette keeps your look modern and refined. This year, designers are leaning into warm leathers, suede textures, and subtle details like contrast stitching or angled heels.
Talbots Harper Suede Block Heel Ankle Boots
These booties pair beautifully with straight-leg denim, midi skirts, and tailored trousers, making them a true wardrobe workhorse. For women over 50, they offer height without hassle and polish without pressure.
Shop Beth’s Block Heel Bootie Collection
Modern Brogues, Oxfords & Loafers– Menswear-Inspired, Timelessly Chic
Brogues and oxfords are making a strong comeback this fall—and they’re more versatile than ever. These menswear-inspired shoes offer just the right balance of structure and elegance, making them perfect for smart-casual dressing. Look for styles in soft leather or suede, with subtle detailing like perforation or contrast soles. They’re ideal for women over 50 who want something polished, walkable, and endlessly wearable with trousers, denim, or midi skirts.
Sam Edelman Loraine Bit Loafers
And if you’re already a fan of loafers—good news: they’re still going strong this season. Sleek, minimal loafers or chunkier lug-sole versions are both on-trend, giving you even more options in the menswear-meets-feminine category. Think of brogues, oxfords, and loafers as your style-forward trio for elevated everyday wear.
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YouTube
Unveiling the Hottest Fall & Winter Shoe Must-Haves
Fall/Winter 2024 gave us timeless shoe moments—and they’re not going anywhere. From block heel booties to sleek knee-high boots, the styles that defined last season are continuing to trend in 2025. Many of the same silhouettes are still front and center this season—refreshed with new textures, finishes, and subtle updates.
In the video below, Beth walks through her favorite fall shoe trends from last year—and you’ll spot many of those same styles in this year’s roundup, too.
How to Style those Fall & Winter Shoes? Check out More Style Inspiration on the Blog:
- 7 Ways to Look Expensive on a Budget This Fall
- What to Wear in the Fall: Chic Outfit Ideas for Women Over 50
- 7 Transitional Outfits to Wear From Summer Into Fall
Knee-High Boots – The Silhouette That Defines Fall & Winter Style
Knee-high boots are a fall essential—and this year, they’re back in a big way. What makes them so timeless is their ability to instantly elevate an outfit while also providing warmth and coverage. Whether worn over skinny jeans, under midi skirts, or with sweater dresses, they add a refined, put-together feel that’s both practical and flattering.
Talbots Tish Suede Stretch Riding Boots
Look for styles in smooth leather or suede, with comfortable low or mid-height heels. For women over 50, a classic knee boot is a confidence-boosting staple that never goes out of style.
Shop Beth’s Knee-High Boots Collection
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Fashion Sneakers – Comfortable Meets Chic
Fashion-forward sneakers have earned their place in every fall wardrobe. These aren’t your gym shoes—they’re elevated, everyday essentials that bring comfort to your casual outfits without sacrificing style. This season, look for sleek leather finishes, minimalist designs, or subtle platforms that give a little lift.
Rothy’s Original Slip-On Sneakers
Pair them with relaxed denim, sweater sets, or even casual dresses. For women over 50, they’re a great way to stay current while staying comfortable—because nothing beats a shoe you can walk in all day.
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Frequently Asked Questions
Fall and Winter Shoes for Women Over 50
Q. How do I wear brogues or oxfords without looking too masculine?
A. It’s all in the styling. Pair them with soft, feminine pieces like a midi skirt, wide-leg trousers, or a blouse with texture or detail. A pointed-toe brogue or one in suede or patent leather can also soften the look and feel less androgynous.
Q. Are tall boots still in style for women over 50—or should I stick to ankle boots?
A. Tall boots are very much back in style, and they’re incredibly flattering. Choose a sleek, classic pair in leather or suede with a low to mid heel. They look especially elegant with sweater dresses, midi skirts, or tucked-in jeans—no age limit required.
Q. I love sneakers, but how do I wear them without looking too casual?
A. Look for structured, neutral-tone sneakers in leather or suede, and pair them with elevated basics—think tailored pants, trench coats, or a polished knit. Add accessories like a structured bag or layered jewelry to keep the look intentionally casual, not sloppy.
Statement Flats – Bold, Beautiful, and Built for Comfort
Flats don’t have to be boring—and this fall, they’re making a statement. Whether it’s a pointed toe, metallic sheen, animal print, or velvet texture, these flats are designed to be seen. Ideal for women who prefer a lower heel without giving up on style, statement flats are a fantastic option for both work and weekend.
Statement flats add a touch of personality to even the simplest outfit, and they transition beautifully from day to night. Bonus: they travel well and won’t leave your feet begging for a break.
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Weather-Resistant Picks – Practical, but Make It Pretty
Just because it’s wet or chilly outside doesn’t mean you have to compromise your look. Weather-friendly shoes are more stylish than ever this season, with waterproof leather, rubber lug soles, and cozy linings that keep you warm and dry. Think sleek Chelsea boots, stylish duck boots, or shearling-lined slip-ons that blend fashion and function seamlessly.
Waterproof Laguna Chelsea Boots
For women over 50, having one pair of weather-ready shoes you actually want to wear makes all the difference in staying stylish through the season.
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✨ Beth’s Style Wisdom
Fall and Winter Shoes for Women Over 50
The right pair of shoes doesn’t just complete your outfit—it can completely change how you carry yourself. As we mature, we become more selective about comfort, but that doesn’t mean sacrificing style. I always recommend investing in a few versatile pairs that mix polish with practicality. Stick with rich, timeless materials—leather, suede, velvet—and don’t shy away from a bold detail or two. A modern shoe with great support can make even the simplest outfit feel intentional.
Closing Thoughts
Fall and Winter Shoes for Women Over 50
Fall and winter style starts from the ground up—and the right shoes can instantly elevate how you look and feel. Whether you’re drawn to timeless knee-high boots, classic brogues, or fashion-forward sneakers, this season’s trends prove that style and comfort don’t have to be mutually exclusive—especially for women over 50. Many of these silhouettes are here to stay, which makes them smart additions to your wardrobe. I hope today’s roundup of Fall and Winter Shoes for Women Over 50 gives you a little inspiration (and maybe an excuse to refresh your shoe lineup). Which pair are you excited to step into this season?
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