From 35 To 75—These 10 Shoes Are Always In Style

I’ve spent decades watching fashion trends come and go, but some shoes remain timeless.

Good shoes aren’t just about looking sharp—they’re investments that carry you through life’s moments with comfort and confidence.

No matter your age, certain footwear classics have earned permanent spots in our closets because they strike that perfect balance between function and style.

Here are my top picks for shoes that look appropriate and feel amazing, whether you’re 35 or 75.

1. Classic Leather Loafers

My first pair of penny loafers lasted nearly eight years—worth every cent I paid. These slip-on wonders bridge the gap between casual and formal with remarkable ease. The leather molds to your feet over time, creating a custom fit that feels like they were made just for you.

Men’s versions with tassels or penny slots have graced boardrooms since the 1950s, while women’s styles range from chunky-soled statements to sleek, minimal designs. I particularly love how they work with both tailored trousers and weekend jeans.

For anyone with foot pain or comfort concerns, loafers offer substantial support without sacrificing style. Plus, they’re one of the few shoes that actually look better with a bit of wear and character.

2. White Leather Sneakers

Nothing refreshes an outfit faster than crisp white sneakers. I once thought these were strictly for the young crowd until my 68-year-old mother started wearing them with everything from summer dresses to wool trousers.

The magic lies in their simplicity. Clean lines and minimal branding create a canvas that works across generations. Brands like Adidas Stan Smiths and Common Projects have perfected designs that never try too hard or scream for attention.

Caring for white sneakers becomes almost meditative—a quick wipe after wearing keeps them looking sharp. When shopping, opt for full leather rather than canvas for longevity. The slight price increase pays off in years of additional wear and improved comfort as they conform to your feet.

3. Ankle Boots With Stacked Heels

Ankle boots saved my wardrobe during those awkward seasonal transitions. The stacked heel provides just enough height (typically 1-2 inches) without sacrificing stability—critical as we age and balance becomes more precious.

Black leather remains the gold standard for versatility, but rich brown and even deep burgundy offer beautiful alternatives. The best designs feature clean lines without excessive hardware or trendy details that quickly date them.

My favorite pair has a slightly almond-shaped toe that elongates the leg without pinching. When buying, ensure you can wiggle your toes comfortably and that the ankle opening accommodates pants without awkward bunching. These boots transition effortlessly from work meetings to weekend outings, making them perhaps the hardest-working footwear in my closet.

4. Ballet Flats With Cushioned Soles

Ballet flats earned their iconic status for good reason. My grandmother swore by them, my mother collected them, and now I find myself reaching for them several times weekly. The key is finding pairs with proper arch support and cushioned soles—features that weren’t always available in earlier decades.

Modern versions from brands like Margaux and Rothy’s have revolutionized this category with memory foam insoles and flexible construction. The rounded toe box accommodates foot changes that naturally occur with age, while the low-cut vamp creates a flattering line on the foot.

For maximum versatility, start with black or camel leather, then branch into subtle patterns or textures. A slight elastic around the topline prevents slipping without creating unsightly gaps or pinching. These shoes truly prove that comfort and elegance aren’t mutually exclusive.

5. Block-Heel Pumps Under Two Inches

After years of torturing my feet in stilettos, discovering block heels felt like salvation. The wider surface area distributes weight more evenly, reducing pressure on the ball of the foot and preventing that dreaded burning sensation after hours of wear.

A height between 1.5-2 inches hits the sweet spot of elevation without compromising stability. I’ve found suede finishes offer subtle elegance for special occasions, while leather provides everyday durability. The best designs feature a slightly rounded or softly squared toe rather than extremely pointed styles that compress toes unnaturally.

For anyone navigating arthritis or joint issues, look for pairs with extra padding at pressure points and consider half-inserts for customized comfort. These practical yet polished shoes have carried me through countless weddings, interviews, and milestone celebrations with dignity intact.

6. Leather Driving Moccasins

Road trips introduced me to driving moccasins, but their comfort quickly made them my go-to for everyday errands. Originally designed for gripping car pedals, these shoes feature flexible rubber-nubbed soles that provide surprising traction and conform to natural foot movement.

The slightly raised heel and cushioned footbed make them ideal for those with plantar fasciitis or heel pain. Unlike many flats, driving mocs typically include proper arch support while maintaining a sleek profile. The leather upper stretches gracefully over time without losing structure.

Color options abound, but I’ve found navy, tan, and deep green offer year-round wearability. The hand-stitched toe detail adds craftsmanship without flashiness. For those between sizes, sizing up slightly accommodates natural foot swelling throughout the day—a thoughtful consideration as we age.

7. Walkable Slingback Sandals

Summer footwear often forces uncomfortable choices between style and comfort. Slingbacks solve this dilemma beautifully. The adjustable back strap accommodates natural foot swelling during warmer months while providing crucial stability that flip-flops lack.

My search for the perfect pair ended with a design featuring a contoured footbed and slight platform. The minimal 1-inch heel elevation improves posture without strain. Premium versions include leather linings that prevent the dreaded foot-stick during humid days.

Neutral colors extend wearability, but don’t overlook metallics—they function surprisingly well as neutrals while adding subtle interest. The exposed foot creates a lengthening effect on legs while allowing proper air circulation. For anyone with bunions or width concerns, look for styles with adjustable front straps that accommodate foot shape without highlighting problem areas.

8. Woven Leather Huaraches

Huaraches represent perhaps the oldest continuously worn shoe design in my collection. These Mexican-origin woven leather sandals have withstood centuries of fashion shifts for good reason—they combine breathability with surprising support.

Modern iterations feature cushioned insoles while maintaining the distinctive woven upper that flexes with movement. The closed toe provides more protection than typical sandals, making them suitable for light garden work or casual walks. They pair with linen pants, summer dresses, and even tailored shorts.

The natural leather develops a beautiful patina over seasons, telling the story of your adventures. For those with sensitive feet, the woven design accommodates slight width fluctuations without pressure points. Unlike many trendy summer shoes, quality huaraches can last a decade or more with basic leather care—making them both sustainable and economical.

9. Waterproof Chelsea Boots

Rain once meant sacrificing style for practicality until I discovered waterproof Chelsea boots. The elastic side panels make them easy to pull on—no bending or struggling with laces required. This feature becomes increasingly valuable as mobility changes with age.

Modern manufacturing techniques have created waterproof leather that doesn’t look obviously synthetic or plasticky. The ankle height provides splash protection without restricting movement. I particularly appreciate the cushioned collar that prevents uncomfortable rubbing.

The clean, minimal design transitions seamlessly from wet weather to indoor settings without looking like obvious rain gear. For maximum versatility, consider a lug sole for traction without excessive bulk. These boots have carried me through countless downpours while keeping feet dry and comfortable—proving that practical footwear needn’t look orthopedic or utilitarian.

10. Cushioned Walking Oxfords

European vacations taught me the value of proper walking shoes. After limping through cobblestone streets in inappropriate footwear, I discovered cushioned Oxfords—now an essential for any trip involving significant exploration.

The lace-up design provides customizable security while the slightly rounded toe accommodates natural foot spread during long days. Modern versions incorporate athletic shoe technology with traditional styling, creating hybrids that don’t scream “comfort shoe” aesthetically.

Leather remains the preferred upper material for its breathability and ability to conform to the foot’s shape. For anyone managing neuropathy or circulation issues, look for styles with extra depth and removable insoles that accommodate custom orthotics. These shoes represent the perfect marriage of tradition and technology—classic enough for business casual settings yet engineered for serious mileage.