7 Essential Shoes Every Man Should Own—and When to Wear Them
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- May 31, 2025
A man’s wardrobe is only as strong as his foundation—and that starts with his shoes. Every man needs a versatile footwear collection that can effortlessly transition from casual outings to formal occasions.
Whether you’re heading to the office, hitting the town, or relaxing on the weekend, the right pair of shoes not only completes your outfit but also speaks volumes about your style and attention to detail.
STYLEAFRIQUE™•com has curated a guide to seven essential shoes every man should have in his wardrobe, along with tips on when to wear them.
1. Classic Oxford Shoes
When to Wear Them: Formal events, job interviews, weddings, and business meetings.
A timeless staple in any gentleman’s closet, the Oxford shoe is defined by its closed lacing system and sleek silhouette. Typically crafted in leather, black Oxfords pair perfectly with a suit or tuxedo, making them ideal for high-formality occasions. Brown versions can slightly tone down the formality while remaining polished and sharp.
2. Derby Shoes
When to Wear Them: Business-casual offices, dinner dates, smart-casual events.
Slightly less formal than the Oxford, the Derby features an open lacing system that makes it a touch more relaxed. It’s a versatile choice that works well with tailored trousers, chinos, or even dark denim. A brown or oxblood leather pair is an excellent go-to for day-to-night transitions.
3. Loafers
When to Wear Them: Casual Fridays, weekend brunch, summer weddings, travel.
Loafers are the ultimate blend of comfort and style. With no laces to fuss over, they are easy to slip on and off, making them ideal for casual outings and laid-back office environments. Choose a suede or polished leather pair to elevate your casual look; they pair well with chinos, tailored shorts, or even jeans.
4. Chelsea Boots
When to Wear Them: Date nights, casual office days, nights out, and fall/winter weekends.
Chelsea boots are sleek, ankle-high boots with elastic side panels, offering both comfort and style. Black leather versions elevate smart-casual looks, while brown suede pairs well with denim or corduroy. They’re ideal for transitional weather and effortlessly bridge the gap between casual and dressed-up.
5. Brogues
When to Wear Them: Semi-formal settings, creative workplaces, weddings, and dinners.
Brogues are defined by their decorative perforations and can come in Oxford or Derby styles. Wingtip brogues in tan or chestnut leather add character to otherwise plain outfits. They strike a balance between formal and casual, making them a great choice when you want to show a little personality.
6. Sneakers
When to Wear Them: Everyday casual, weekend errands, laid-back social events.
Sneakers are a must-have for those who value comfort without sacrificing style. Whether you prefer classic canvas sneakers, classic white sneakers or trendy athletic styles, there’s a shoe for every casual scenario. They pair with almost anything—jeans, chinos, shorts, or even casual suits, making them perfect for running errands or meeting friends for coffee.
7. Sandals
When to Wear Them: Beach days, summer parties, casual outings.
When the temperature rises, a good pair of sandals is essential. Look for stylish options like leather slides or flip-flops for the beach, or opt for more supportive designs for everyday summer wear. They’re perfect for throwing on after a swim or for casual outings in the sun.
