A well-rounded shoe collection is the cornerstone of effortless style, and 2025 highlights the perfect blend of comfort, function, and timeless appeal. Whether dressing up for a formal event, running errands, or enjoying a casual outing, having the right timeless shoe styles for men ensures you’re always prepared. From iconic loafers to contemporary mules, this curated list showcases the essential footwear every man needs to achieve both practicality and sophistication for any occasion.
10 Timeless Shoe Styles for Men to Own
1. Chunky Sneaker
Some outfits call for a bold statement, and that’s where the chunky sneaker steps in. Known for its oversized sole and exaggerated design, this style adds a touch of personality and enhances comfort and support. Whether you’re aiming for a streetwear-inspired look or need extra presence in your footwear, chunky sneakers offer the perfect balance of function and fashion.
Technical options like Asics Gels bring a performance-driven aesthetic, offering durability and a sporty edge that works well with athletic and casual outfits. On the other hand, a cleaner silhouette like the New Balance 990v5 provides the same substantial feel but in a more refined package, making it a great choice for those who want extra size without overwhelming their look. Whether paired with relaxed denim, cargo pants, or even tailored joggers, chunky sneakers inject energy into any wardrobe while keeping things comfortable and on-trend.
2. Slim Sneaker
While chunky sneakers bring boldness, a sleek, slim sneaker is the understated essential that every man needs. Defined by its low-profile silhouette and minimalist aesthetic, this style seamlessly complements a wide range of outfits, from casual to smart-casual. It’s the go-to option to keep things refined and effortless without paying too much attention to your footwear.
Timeless choices like the Adidas Samba or Converse Chuck Taylor 70 offer a perfect blend of style and versatility. The Samba, with its leather upper and classic gum sole, pairs effortlessly with tailored trousers, jeans, or even shorts, while the Chuck 70 brings an old-school charm that works with everything from relaxed fits to contemporary streetwear. Whether you’re dressing up or down, a slim sneaker ensures a clean, polished look without unnecessary bulk, making it an enduring staple in any wardrobe.
3. Loafer
Loafers are the ultimate blend of ease and sophistication, making them one of the most versatile shoes a man can own. Their slip-on design offers effortless wearability, while their sleek silhouette ensures they remain stylish across various outfits. Whether you’re dressing up for a dinner date or keeping it casual on the weekend, loafers transition seamlessly between different looks. A black leather pair adds an edge to denim, brown suede pairs beautifully with chinos, and even a well-crafted penny loafer can elevate tailored shorts in warm weather.
For those just stepping into the world of loafers, a sturdy and slightly rugged option like Dr. Martens provides a modern, casual introduction. The chunky sole and durable leather make them a great everyday staple. As style evolves, upgrading to a refined classic like J.M. Weston’s 180 loafer or Alden’s hand-stitched penny loafer delivers an elevated, timeless look. With the right pair, loafers can be the footwear that effortlessly bridges the gap between
4. Running Shoes
With running making a strong comeback in fitness and fashion, a solid pair of running shoes is a must-have. Whether training for a marathon, hitting the pavement for a casual jog, or embracing the athleisure aesthetic, the right running shoe blends performance with everyday style. Comfort, support, and durability are key factors when choosing a pair that can handle high-intensity workouts and laid-back city strolls.
For all-day comfort and a cushioned ride, Hoka One One delivers with its signature chunky sole and cloud-like support, making it a favorite for runners and sneaker enthusiasts. On the other hand, the Nike Zoom Vaporfly is a go-to for serious runners who need a lightweight, responsive shoe for race days or intense training sessions. Whether you’re in it for the miles or just the effortlessly sporty look, a quality running shoe ensures both peak performance and off-duty style.
5. Dress Shoe
Once the cornerstone of every man’s wardrobe, dress shoes have evolved from rigid formality to a more versatile essential. While classic silhouettes like Oxfords and derbies remain timeless, today’s styles emphasize adaptability—allowing a single pair to transition between formal and smart-casual looks easily. Whether you’re dressing up for a wedding, an important meeting, or a polished night out, having the right dress shoes ensures you balance sophistication and practicality.
For a traditional yet contemporary option, an Oxford black or deep brown shoe is a refined choice that works seamlessly with suits and tailored ensembles. If you prefer something more relaxed but still elegant, a derby shoe like the Paraboot Michael blends craftsmanship with a slightly chunkier sole, making it ideal for business attire and off-duty looks. You invest in a timeless style beyond formal occasions by choosing a versatile dress shoe.
6. Hiking or Work Boot
A sturdy pair of boots is more than just a rugged style statement—it’s necessary for durability, support, and versatility. Whether tackling challenging terrain, braving unpredictable weather, or adding a raw edge to a casual outfit, a well-crafted hiking or work boot provides both function and fashion. These boots are built to withstand the elements while offering all-day comfort, making them a must-have for any well-rounded wardrobe.
The Red Wing lace-up boot is a time-tested favorite for a classic and dependable choice, known for its high-quality leather and longevity. Meanwhile, the Blundstone 500 delivers a slip-on Chelsea-style work boot that blends ease and toughness, perfect for daily wear. If you’re looking for something with a nostalgic, fashion-forward twist, a vintage-inspired hiking boot—such as those seen in Frank Ocean’s effortlessly cool styling—can add personality while keeping your feet prepared for adventure.
7. Dress Boot
A well-made dress boot is the perfect fusion of refinement and edge, offering a sleek alternative to traditional dress shoes while maintaining a polished aesthetic. Whether navigating a formal setting, elevating a smart-casual outfit, or simply looking for a versatile boot that pairs effortlessly with tailored trousers or denim, a high-quality dress boot is a must-have in any modern wardrobe.
For timeless sophistication, the R.M. Williams leather Chelsea boot remains an unbeatable classic, crafted with a seamless one-piece leather upper and a sleek silhouette that transitions effortlessly from business attire to evening wear. If you’re drawn to a more contemporary yet equally refined option, the Our Legacy Camion boot adds a bold touch with its robust sole and slightly more rugged appeal. Whichever style you choose, a dress boot ensures you step out confidently, blending craftsmanship and versatility in a way that suits classic and modern tastes.
8. Sandal
A well-chosen sandal is the ultimate balance between comfort and effortless style, making it a year-round essential in warmer climates. While casual flip-flops like Havaianas serve their purpose, a more refined option elevates your look without sacrificing ease. The right pair of sandals can transition seamlessly from the beach to the city, offering practicality and a fashion-forward edge.
Birkenstocks remain a staple for a timeless and versatile choice, thanks to their contoured footbed and classic leather or suede straps. If you prefer something with a more modern, utilitarian feel, Merrell Hydro Mocs provide a lightweight, water-resistant option that pairs well with relaxed summer outfits. Whether strolling through the city, heading to the coast, or lounging at home, a thoughtfully selected sandal ensures you stay cool while keeping your style sharp.
9. Mule
Once overlooked, mules have made a serious comeback, proving that effortless slip-on footwear can still be stylish. Striking the perfect balance between formal and casual, they offer a refined yet relaxed look that works across multiple settings. Whether heading to a laid-back brunch, stepping out for an evening event, or just looking for an easy yet polished alternative to sneakers, mules provide both convenience and sophistication.
For a sleek, minimal take, the Our Legacy Camion mule delivers a modern edge with its structured leather build and understated design. Troentorp’s clogs bring a touch of Scandinavian craftsmanship with a bold, chunky silhouette if you’re drawn to a more artisanal, fashion-forward approach. No longer just a niche choice, mules have cemented their place in contemporary menswear, offering an effortless way to refine your wardrobe.
10. Indoor Shoe
An often-overlooked essential, indoor shoes bring comfort and style to your at-home wardrobe. Whether lounging on a slow Sunday morning or working from home, the right pair ensures warmth, support, and an effortless sense of refinement. Unlike everyday slippers, a well-chosen indoor shoe blends comfort with a polished aesthetic, allowing you to move seamlessly from relaxation to casual hosting without sacrificing style.
For a luxurious, minimalist take, The Row’s Canal loafer offers a sleek, structured look that pairs well with loungewear or relaxed tailoring. Classic Uggs provide plush warmth on the cozier side, making them perfect for colder months. Whether you prefer a refined leather option or a plush shearling-lined pair, investing in a stylish indoor shoe keeps you feeling put together—even when you’re staying in.
Crafting the Perfect Shoe Collection for Every Occasion
A great shoe collection is all about versatility, comfort, and style; these ten essential pairs ensure you’re covered for any occasion. Whether stepping into a sleek pair of loafers for a night out, lacing up chunky sneakers for a bold streetwear moment, or slipping into a refined mule for effortless sophistication, having the proper footwear makes all the difference. By investing in quality, well-designed shoes that fit your lifestyle, you’re not just keeping up with trends—you’re curating a collection that blends timeless appeal with modern practicality. With these staples in your wardrobe, you’ll always have the perfect pair to complement your style, no matter where the day (or night) takes you.
