This winter, fashion’s spotlight is shining squarely on two wardrobe staples: ankle boots and oversized outerwear. With the temperatures dropping and style stakes rising, women over 40 are finding new ways to blend comfort, confidence, and bold statements in their cold-weather looks. From Parade’s celebrity stylist Brenda Cooper to the trend forecasters at Fashion.ie, the message is clear: this season is all about making your outerwear and footwear the heroes of your outfit.
On October 26, 2025, Parade published styling guidance by Morgan McMurrin, featuring Brenda Cooper—a veteran stylist whose client list includes Fran Drescher, Jamie Lee Curtis, and Molly Shannon. Her advice? Flat ankle boots are the ultimate choice for women over 40, offering a rare combination of comfort, style, and versatility for the fall and winter months. Flat ankle boots are a perfect choice for when you are over 40, as they will take you through the fall and winter seasons with comfort, style and versatility, Cooper explains, according to Parade.
But not just any outfit will do. Cooper is quick to point out that the key to flattering ankle boots lies in creating a smooth, uninterrupted line from hip to toe. She recommends pairing them with jeans, slacks, or even a maxi skirtas long as the skirt has some movement to reveal those stylish boots. When styled intentionallysay, with a maxi skirt that has a bit of movement in the fabric so it gives a glimpse of the bootsthe look can become an effortlessly boho outfit and beautifully balanced, she notes.
What should women steer clear of? According to Cooper, cropped pants are a no-go. Flat ankle boots create a visual break at the ankle that shortens the leg line, especially when paired with cropped pants, she stresses. Super long flared pants and floor-length dresses are also off the table, as they either hide the boots or disrupt the outfits proportions. Pants that bunch at the ankle? When pants bunch or gather at the top of an ankle boot, they disrupt the clean line of the leg and add unnecessary bulk, Cooper says, emphasizing that its all about maintaining a streamlined silhouette.
So, what does work? Cooper offers a treasure trove of outfit ideas. Black leggings and flat ankle boots make for a relaxed, rocker-chic lookperfect for errands or casual weekends. Leather leggings elevate the vibe, adding urban sophistication, especially when paired with a structured crossbody bag or statement watch. Tights and boots, especially under a long leather coat, create a confident, timeless ensemble suitable for city outings or art openings.
Bootcut jeans with ankle boots bring a vintage-meets-modern twistthink crisp blue shirts, playful ties, and maybe a tailored blazer for polish. For those willing to take a risk, colorful flat ankle boots (mustard yellow, anyone?) can inject personality into a classic camel coat. High-rise jeans, as seen on Reese Witherspoon, and skinny jeans with earthy brown boots are both effortless and chic, whether for travel days or casual Fridays. And dont forget skirts: a teal skirt with opaque tights and dark boots elongates the legs, especially when topped with an asymmetrical coat.
Accessories, Cooper insists, are the finishing touch. Scarves, bold earrings, hats, statement brooches, or patterned silk scarves can all elevate a look, drawing attention to the face and adding that all-important personal flair. Flat ankle boots never go out of style, and each season brings fresh new interpretations of them, she assures readers, making them a wise investment for years to come.
But what about the rest of the outfit, especially when it comes to outerwear? On October 27, 2025, Fashion.ie’s Kevin O'Brien outlined the outerwear trends dominating winter wardrobes this year, and they’re nothing short of dramatic. Oversized silhouettes, sculptural coats, and statement-making details are everywherefrom floor-length puffers with balloon sleeves to coats with exaggerated lapels and cocoon shapes.
This season, outerwear isnt just about warmth; its the main event. According to Fashion.ie, Oversized coats and jackets are being touted as the bigger, the better. Statement outerwear is described as wearable artthink architectural volume, bold proportions, and textures that beg to be touched. Faux fur, shearling, puffer extremes, and eye-catching prints or colors like electric blue, neon orange, and pastel lavender are all in play.
Styling these bold pieces requires a deft hand. The experts recommend balancing voluminous coats with slimmer bottomsskinny jeans, tailored trousers, or sleek boots. Let the coat be the star by keeping the rest of the outfit simple and monochrome. If youre feeling adventurous, a bright or patterned coat can be paired with neutral basics, while a neutral, oversized coat can be livened up with a pop of color in your accessories.
Material matters just as much as silhouette. This winter, tactile luxury rules: faux fur, shearling, teddy fabrics, and oversized leather or suede are all making waves. For texture-heavy coats, keep the rest of your look simple to maintain focus. Mixing materialslike layering a leather jacket under a wool coat or combining shearling with wooladds depth without chaos.
Investment advice from Fashion.ie is practical: choose a silhouette that will last several seasons. Neutrals offer longevity, while bold colors make a maximal statement. Functionality is key, toolook for good insulation, waterproof finishes, and room for layering. Sustainability is increasingly important, with recycled fillers, cruelty-free faux fur, and eco-friendly finishes becoming the standard for conscientious shoppers.
Statement details like dramatic collars, funnel necks, and exaggerated shoulders add architectural interest and frame the face. Cape-like shapes and coat-dress hybrids blur the line between outerwear and garment, offering even more ways to stand out. For these pieces, keep accessories minimal and fitted, letting the coat do the heavy lifting.
Ultimately, both Cooper and O'Brien agree: this winter is about confidence and self-expression. Whether youre slipping into a pair of timeless ankle boots or wrapping yourself in a cocoon of faux fur, let your wardrobe reflect your personality and lifestyle. Invest in quality, experiment with color and texture, and above all, wear your choices with pride. The colder it gets, the bigger your fashion impact can beso why not make your boots and coat the stars of the show?
