When it comes to men’s dress shoes, there are countless rules passed down from one generation to the next (some useful, some perplexing). Many of us have heard the advice to avoid brown shoes in the city, not to wear brown after 6:00 PM, or not to do business with a man that’s wearing loafers. These “pearls of wisdom” were passed down by our grandfathers when we were still figuring out which end of a shoehorn to use.
For many of us, stepping into a proper bootmaker for the first time was a bewildering experience, like navigating a foreign city, overwhelmed by the dizzying selection of hand-made shoes. If you’re confused by the countless shoe options out there, an easy and reliable choice is to look for Italian-inspired mans footware.
Italian craftsmanship has long been revered for its attention to detail, so you can trust that these shoes are not just stylish but also well-made, comfortable, and durable. The finesse of Italian design can instantly elevate any outfit, whether you’re dressing up for a formal event or just want to refine your daily outfits. You’ll naturally turn heads, exuding an unmistakable Italian elegance that speaks a lot without saying a word. Read on to dive into the world of dress shoes with confidence, understanding, and a little less confusion than your first visit to the bootmaker.
Oxford Shoes
Why are Oxfords so popular? The Oxford is the gold standard when it comes to formal footwear. With its clean lines and closed lacing, where the eyelets are stitched under the vamp, it delivers a sharp, polished look that fits right in at the office or any formal occasion. The sleek, minimal design on this mens footwear makes them look clean and professional, which pairs effortlessly with tailored trousers and suits. A cap toe adds enough structure without overdoing it, and black leather is always a safe bet.
Though they started in Scotland and are sometimes called “Balmorals,” today they’re more boardroom than castle. Simple, timeless, and quietly confident, they’re what you wear when you mean business.
Derbys
Derbys are what you reach for when you want a bit more breathing room. With their open lacing system, they have a slightly more relaxed feel than Oxfords, so they’re ideal for business casual days when a full suit might feel like overkill. They’re still smart, just not stiff.
You can wear them with tailored trousers and a sports jacket or dress them down a notch with chinos or dark denim. And while black works well, browns, cognacs, and oxbloods bring out a different character, especially if you’re after an effortless, worn-in charm.
Brogues
This style of mans footwear brings a bit of personality to your outfit without being too flashy. Technically, the term refers to the decorative perforations punched into the leather, which is a throwback to when they were meant to drain water during muddy treks in the countryside.
The modern Brogues are more of a style statement than survival gear. You’ll spot them in different styles, with variations like wingtips that sweep across the toe or more restrained cap-toe designs with just a hint of detailing. Whether you go for polished leather, soft suede, or a grainier texture depends on how casual you want to dress. They’re a good choice when you want something classic, but with a bit of flair.
Monks
Monk straps strike a confident middle ground. They’re not quite as formal as Oxfords, but sharper than Derbys. The bold buckle gives the style a touch of flair that sets it apart from the usual lace-ups.
If you’re after something refined but a little different, this is the style for you. The single strap leans classic and understated, especially in something like deep brown suede, while the double version has a more structured, almost military vibe, which makes a stronger statement. They’re the kind of footwear that quietly says you know what you’re doing, especially when paired with a tailored outfit and a bit of personality.
Loafers
Loafers blend laid-back style with sophistication. It’s easy to spot them in a men’s shoe store by their versatile slip-on design. They work seamlessly with everything from a sharp suit to casual jeans. You can add them to a pair to a relaxed office look or rock them for a weekend outing. You can also easily accessorise with sunglasses or a classic hat for a touch of personality (just like Michael Jackson did) if you’re feeling adventurous.
What makes loafers so great is that you can easily incorporate them into your outfits. They’re simple enough to let the accessories take centre stage, but sharp enough to complement them effortlessly.
Chukkas
Chukkas offer a laid-back yet polished vibe, with their ankle-high cut and simple two- or three-eyelet design. Traditionally crafted from calfskin leather, you can find this men’s shoe online in suede or even black kid leather for a dressier look. The introduction of crepe soles, thanks to Nathan Clark’s observations of soldiers’ footwear in Burma, gave rise to the iconic desert boot style.
You can easily style a tan or brown pair, though it’s best to avoid them with a full suit. The chukka’s easy-going nature makes it a versatile option, ideal for smart-casual outfits that need just a touch of sophistication without feeling too formal.
Chelseas
Chelsea boots bring an effortless cool that few other styles can match. Designed for horse riding, they later found recognition in the music and fashion scenes (thanks to The Beatles and the ’60s style revolution).
What makes them stand out is that sleek silhouette and signature elasticated side panel (although there’s also a zip version) especially if you’re channelling a little retro flair. They slip on easily, sit snug at the ankle, and work just as well with a sharp suit as they do with your go-to jeans and a vintage leather jacket.
Kilties
Lastly, Kilties aren’t your everyday type of footwear. Their fringed leather tongue sitting over the vamp adds some old-school charm and eccentricity to your look. You’ll see them pop up on everything from monk straps and loafers to chukkas. This adds texture and personality without being too loud.
This style is a subtle accessory that sets your outfit apart, the way a good watch or scarf might. Just keep the rest of your look simple and let that fringe do the talking.