We all have that one pair of shoes we’ve worn for years — they’re familiar, comfortable, and maybe even sentimental. But sometimes, what feels like a tried-and-true favorite can actually be quietly aging your overall look. In fact, certain shoe styles — while once considered practical or timeless — might now be doing your outfit and your silhouette a disservice. As a stylist, I’m all for comfort and confidence, but I also believe that what you wear on your feet can either modernize your wardrobe or anchor it in the past. The key? Knowing which shoe styles to rethink, and what to wear instead. Here are 7 shoe styles that may be aging your look more than you realize — and yes, many women still swear by them. The question is: Would you?
1. Overly Chunky Comfort Sneakers
Remember your favorite pair of sneakers that felt like walking on clouds? These overly chunky comfort sneakers might bring back that memory. Despite their unmatched comfort, the thick, orthopedic-style design can feel more clunky than chic. Often associated with practicality over style, they may inadvertently give off an outdated vibe unless carefully styled.
Consider sleek alternatives like streamlined walking sneakers that maintain arch support without the bulk. Brands such as Vionic, Allbirds, or Ecco offer options that blend form and function, ensuring you stay stylish and supported.
Interestingly, while these may not be runway-ready, their rise in popularity among younger fashionistas shows a shift towards prioritizing comfort.
2. Round-Toe Mary Janes (in Bulky Styles)
Picture the charming innocence of Mary Janes, but with a twist that leans towards frumpy. The extreme roundness and thick straps, especially in matte leather or velcro, can evoke a sense of nostalgia rather than modernity. This classic shoe style walks the line between overly youthful and awkwardly dated.
Instead, opt for a sleek Mary Jane with a modern silhouette and minimal hardware to maintain the charm without compromising on style.
Fun fact: Mary Janes date back to the early 20th century, originally designed as children’s footwear, which might explain their enduring playful vibe.
3. Basic Black Orthopedic Loafers
Basic black orthopedic loafers may seem like a safe bet for daily wear, but they often lack the flair needed to elevate an outfit. Without distinct design details or structure, these loafers can inadvertently flatten your overall look, making it appear dated.
To revitalize this classic, look for loafers in rich textures like suede or patent leather, or explore updated shapes with pointed or square toes. These subtle design tweaks can breathe new life into your footwear collection.
Did you know? The loafer became a popular choice due to its slip-on convenience, originating from Norwegian fishermen’s shoes in the early 20th century.
4. Low-Cut Ankle Boots with Too Much Slouch
Slouchy ankle boots have a relaxed appeal, yet too much slouch can disrupt the line of your leg, giving a look that’s more disheveled than chic. This excess slouch or bagginess can result in an unpolished appearance, breaking the silhouette.
Consider structured ankle boots with a slight heel and a cleaner fit around the ankle to maintain a sleek profile. A well-fitted boot can enhance your outfit by effortlessly elongating the leg line.
Intriguingly, ankle boots first gained popularity in the 19th century and have since been a staple in women’s fashion for their versatility.
5. Orthopedic Velcro Sandals
Sandals with thick Velcro straps and rubber soles often choose function over fashion, potentially aging the wearer. While undeniably practical, the overtly utilitarian design can overshadow style, making them an unflattering choice for many outfits.
Opt for stylish comfort sandals with hidden support; brands blending style with footbed technology provide a more modern look while retaining comfort.
A quirky tidbit: Velcro fastening was inspired by the way burrs cling to animal fur, a discovery made by Swiss engineer George de Mestral in the 1940s.
6. Overly Practical Flats (With Zero Shape)
Flats that lack shape or structure, often in dull colors, can unintentionally suggest a disregard for style. These overly practical flats might seem like the easy choice, but they can detract from a polished look.
Instead, seek out flats with interesting textures, colors, or subtle embellishments to add a touch of sophistication and life to your wardrobe.
Interestingly, the ballet flat revolutionized women’s footwear in the 1950s, transitioning from dancewear to a fashion staple celebrated for its elegance and comfort.
7. Heavy Clogs or Mule Hybrids (With Thick Soles)
Clogs and mules have had their moments in fashion, often celebrated for their unique style. However, when they come with thick, heavy soles, they can look more dated than desirable. These styles can feel clunky, especially when paired with casual outfits.
For a more modern twist, consider sleek mules with a low block heel or a lightweight sole to maintain the essence without the heaviness.
A fun tidbit: Clogs have been around since medieval times, originally designed to protect feet from harsh conditions, which explains their enduring rugged appeal.