5 Shoes Every Man Should Own

Whether you’re heading to a first date, attending an important meeting, or simply going about your day, dressing well is always a priority. While many men focus on their bespoke suits and tailored shirts, one crucial detail is often overlooked — shoes.

In reality, your footwear can define your entire look. The right pair of custom-made shoes not only complements your outfit but elevates your overall presence.

So where should you start? With the essentials. Here are five must-have styles every modern gentleman should own to complete his bespoke wardrobe.

Black Oxfords

Occasion: formal, business, or professional attire
Material: leather

Atrue classic, black Oxfords are the foundation of formal footwear. With their sleek closed-lacing system and refined silhouette, they are the perfect companion to bespoke suits and tuxedos. Whether you’re attending a formal event, a wedding, or an important business meeting, a pair of black leather Oxfords ensures a polished and timeless look.

• Our Favorite Combinations:
  – Dress them up with a formal bespoke black suit or tuxedo.
• – Wear them to work with your favorite C&C bespoke suit and crisp white shirt. Be sure to add a pop of color or print with a silk pocket square and complimenting a sevenfold tie.

Brown Derby

Occasion: professional or casual attire (think smart to smart casual)
Material: leather

A footwear go-to for modern men, brown derby shoes were originally designed with real holes to help drain the water from the marshy bogs of Scotland. The traditional perforations along with the shoes upper section, called the brogueing, provide this style of footwear a distinctive element others shoes simply lack. Although made in many shades of brown, we recommend opting for a shade of medium brown, which will pair with almost any color slacks or chinos other than black. Less formal than the oxford shoe, brown derbys provide a smart and refined look while remaining comfortably chic.

Our Favorite Combinations:
– Bespoke chinos with a collared dress shirt and a pair of two-toned brown leather derbies.
– Pair them with your favorite grey blazer and white dress pants.

Tassel Loafers

Occasion: semi-formal, business casual, and casual
Material: suede or leather

Tassel loafers are the epitome of effortless elegance. Their laceless design makes them ideal for warmer climates, while their timeless style ensures versatility across occasions. Often worn without socks, they pair exceptionally well with lightweight bespoke linen suits and relaxed tailoring.

Our Favorite Combinations:
– Pair your tassel loafers with your bespoke linen shorts and a casual shirt for a stylish summer look.
– Wear them with your favorite crew neck and bespoke pinstripe suit for the perfect business casual look.

Double Monks

Occasion: semi-formal or business casual
Material: suede or leather

Unique and fashionable, the double monk shoe is an ideal choice for the contemporary gent. Featuring two buckle closures, instead of traditional laces, monk shoes were originally worn by European monks in the early 1400’s. Offered in a wide range of colors and materials, double monk shoes typically are crafted from leather or suede in black, brown, or burgundy. Depending on the event, you can wear them with socks (formal events) or without socks (casual events).

Our Favorite Combinations:
– Pair your brown double monks with a pair of bespoke classic trousers and navy blue cardigan for a sharp office look.
– Match your burgundy double monks with your favorite pair of blue dress pants, white dress shirt, and classic blazer.

Leather Boots

Occasion: business casual or casual
Material: suede or leather

Rugged and dressy, a pair of leather boots will compliment just about any of your daily looks.
In particular, leather brogue boots work with suit trousers and jeans and everything in between. They’re the perfect voice to inject a smart edge to your rugged look. Similarly, the Chelsea leather boots provide an easy slip-on style of boot, similar to a loafer. Chelsea boots can take you from the office to dinner with friends with ease.

Our Favorite Combinations:
– Team your leather Chelsea boots with a bespoke suit jacket and your favorite jeans for a contemporary take on business casual.
– For a more professional look, pair your leather boots with your favorite pair of chinos.

Collars & Cuffs Handcrafted Shoes

At Collars & Cuffs, we believe that great style lies in the details. That’s why we offer a curated selection of custom-made shoes designed to complement our bespoke suits, tailored shirts, and jackets.

Through our partnership with expert artisans, each pair is crafted with precision, combining traditional craftsmanship with modern design. Whether you’re investing in made-to-measure footwear or exploring ready-to-wear collections, every piece is created with the same attention to detail as our bespoke garments.

Building a strong wardrobe starts from the ground up — and with the right shoes, every outfit becomes complete.

Contact a member of our team to learn more about our bespoke menswear and custom shoe collections.