The Men’s Shoe Guide
Men’s shoes decoded: styles, tips, and when to wear them
Shoes say a lot before you’ve even spoken. They can sharpen a suit, dress down a blazer, or carry you comfortably through a weekend city stroll. They’re not just practical, they’re the anchor of every outfit and often the detail people notice first. A polished Oxford shoe signals precision. A suede loafer hints at easy confidence. A crisp trainer shows you know how to keep things relaxed without losing your style.
The trick? Having the right pair for the right moment. That’s where this guide comes in. We’ve organised it by occasion and then by shoe, so you can skip the second-guessing and head straight to the pair that fits both your wardrobe and your diary. From boardroom meetings to black-tie events, off-duty errands to weddings that run long into the night, we’ve got every step covered. Think of it as a framework, one that makes sure you’re never underdressed, overdressed, or simply stuck in the wrong shoes.
Written By: Melisa Rustemova - Published: 08.09.25
Work Mode: Shoes for Corporate Life
In the workplace, your shoes do more than complete an outfit, they set the tone before you’ve even spoken. Think crisp tailoring, sharp lines, and footwear that communicates reliability and polish. From classic boardroom looks to modern business casual, the right pair can shape how you’re perceived.
Oxford Shoes
When it comes to formal men’s shoes, Oxfords sit at the top. Defined by their closed lacing and streamlined profile, they’re built for precision and sharp tailoring. Black leather Oxfords are the gold standard for boardrooms, pairing perfectly with charcoal or navy suits. For something softer but still refined, this season’s oxblood and deep brown tones bring a subtle modern twist.
Derbies are slightly more relaxed but still maintain a professional edge. Open lacing makes them forgiving for wider feet without compromising elegance. Dark brown derbies anchor lighter grey or tan suits, while suede versions bring a refined touch to business casual separates. They’re the go-to for offices that embrace comfort alongside polish, proving that practicality and style can coexist.
For offices that lean business casual, moccasins strike the right balance between polish and comfort. With their soft construction and hand-stitched detail, they feel relaxed yet still look refined. Pair effortlessly with tailored trousers and lightweight shirts, keeping you comfortable without losing definition. While not as formal as Oxfords or derbies, they’re a strong alternative for days when you want ease without sacrificing professionalism.
Pro Tip: For men with wide feet, derbies and moccasins provide comfort without compromising shape. Trainers, meanwhile, can now be office-appropriate if you choose clean, structured low-tops, perfect for more relaxed dress codes.
Smart but Easy: Daytime Done Right
Smart casual dressing is all about balance, refined enough for a lunch meeting but relaxed enough for an afternoon gallery visit. Here are the pairs that get it right.
Men’s loafers are a true smart-casual staple. With a slip-on design and understated silhouette, they work as easily with chinos and a blazer as they do with denim and a polo. Penny loafers deliver quiet sophistication, while soft suede loafers bring a relaxed edge. This season, chunky-soled loafers are dominating, a subtle update that adds height and presence.
Sitting just at the ankle, chukka boots bring structure without stiffness. Tan suede pairs look sharp with lightweight trousers and open-collar shirts, while darker leather options ground jeans and fine-knit jumpers in cooler months. A versatile all-rounder that transitions effortlessly between seasons.
Dress Boots:
For days when trainers feel too casual, dress boots bridge the gap. Sleek Chelseas' and pared-back lace-ups add refinement to smart-casual outfits, styling easily with tailored shirts and dark denim. Earthy tones like taupe, deep tan, and chocolate brown bring a fresh, modern edge.
After Dark: Shoes That Own the Night
Evening footwear is about presence. These are the shoes that catch the eye, whether on a rooftop bar, at a dinner party, or dancing the night away. Rich textures, bold silhouettes, and subtle details come alive after dark.
Monk straps replace laces with buckles, offering a refined alternative to more standard dress shoes. A polished double monk boasts sleek refinement without the fussy laces and elevates everything from slim navy trousers to a silk shirt. They can cross over into both formal and casual settings, proving a single pair can be remarkably versatile.
If you want comfort without compromise, designer low top sneakers are leading the charge in 2025. Clean, low-profile leather styles from brands like Lacoste, Ralph Lauren, and BOSS pair effortlessly with tailored shorts to t-shirts, but work just as well with jeans and an pullover. A perfect example of how luxury and laid-back can coexist.
With their signature perforated detailing, men’s brogues balance character and formality. Quarter-brogues lean subtle, while full-brogues make a stronger statement. Tan and jewel tones complement textured tailoring beautifully, giving your evening looks depth and dimension. While they’re not ideal for black-tie settings, brogues excel in after-hours environments, pairing effortlessly with tweeds, wool blends, or smart-casual tailoring.
Pro Tip: For weddings, dinner parties, or cocktail evenings, monk straps and luxury dress sneakers offer versatility. Brogues remain a classic, especially in slim, modern cuts.
The Big Occasions: Weddings and Black Tie
When the dress code is black tie or a formal wedding, shoes aren’t optional, they’re the foundation. The right pair honours dress codes, sharpens your tailoring, and ensures you look considered from ceremony to last dance. Formal footwear is about refinement: clean lines, polished finishes, and silhouettes that leave nothing to chance.
Dress Shoes
Classic dress shoes form the backbone of formalwear. Sleek profiles, high-shine and minimal detailing complete tuxedos and suits with ease. Black patent leather remains the standard for black tie, while high-shine brown pairs suit daytime weddings or less rigid dress codes.
Spectator Shoes
For individuality, spectator shoes deliver vintage flair. Defined by two-tone colouring and brogue detailing, they nod to 1930s style. Though less common today, they stand out with tailored separates or heritage-inspired suiting, especially in linen or wool.
Pro Tip: Comfort counts at long events. Opt for cushioned styles or discreetly structured dress boots to stay sharp all night.
Off-Duty: Weekend Steps Sorted
Weekends are about flexibility, shoes that adapt to brunch plans, city strolls, or last-minute meetups without losing their edge.
The ultimate all-rounder. From retro runners to bold chunky soles, trainers slot seamlessly into every man’s weekend wardrobe. Wide-fit trainers or cushioned soles keep comfort in check for long days, while slip-on trainers are a hassle-free option for quick coffee runs. Men’s technical trainers are also defining off-duty style in 2025. Think New Balance 350s, Nike Zoom Vomero, and ASICS Gel-Kayano. Stick to neutral tones for easy pairing with loose denim, cargos, or oversized hoodies. Street-led but elevated, they’re the ultimate weekend staple.
Men’s boat shoes remain a seasonal favourite for a reason. Their low profile pairs perfectly with linen trousers, tailored shorts, and open-collar shirts, making them ideal for coastal breaks and city afternoons alike. Opt for soft suede finishes in muted tones like stone, navy, or grey for a more contemporary take.
Modern sandals have evolved beyond the poolside. Minimal leather slides keep things clean, fisherman sandals add structure, and buckled silhouettes bring just the right amount of edge. Pair with linen tailoring or Cuban-collar shirts for warm-weather polish.
Pro Tip: Fit is everything. Make sure there’s no pinching at the toes or slipping at the heel. Wide-fit trainers and flexible uppers are particularly useful for men with broader feet.
Weather-Proof: Shoes for Every Season
Changing conditions shouldn’t compromise style. With the right seasonal footwear, you’ll stay sharp whether facing down rain, frost, or long commutes.
A timeless essential. Sleek, ankle-high, and elastic-sided, Chelsea boots transition easily between work and weekend. Suede Chelsea boots bring a softer look when worn with slim trousers and a wool overcoat, while polished leather versions pair perfectly with tailoring or even skinny jeans. Lug soles are trending in 2025, adding grip and a rugged edge without losing refinement.
Durable and dependable, work boots balance function with rugged style. Whether in lace-up or slip-on designs, they pair naturally with denim, cargo trousers, or utility jackets. Look for cushioned insoles and water-resistant finishes like Timberland boots, for everyday wear that doesn’t compromise on comfort.
Rainy weekends call for protection, and wellie boots deliver. Waterproof, tall, and built for the elements, they’re best styled with jeans and a waxed jacket to keep you dry without sacrificing your look. A must-have for unpredictable weather.
Pro Tip: A good pair of leather boots only gets better with age. With the right care, they develop a patina that tells your story, season after season.
The Final Word
Shoes define occasions, but modern dressing thrives on flexibility. Trainers can dress up into smart casual, boots can ground both suits and denim, and loafers can move seamlessly between day and night. From Oxfords and brogues to sandals and slippers, men’s footwear remains the cornerstone of every wardrobe.
The modern wardrobe thrives on flexibility: loafers that move from day to night, Chelseas that work across seasons, and dress sneakers that redefine evening style. Build a collection that works as hard as you do, because when your shoes are right, everything else falls into place.