The Ultimate Guide to Men's Dress Shoes: Styles for Every Occasion

Andrew Jackson, 7th President of the United States.

While Andrew Jackson wasn't talking about literal shoes, his words still ring true. Big shoes (or the right ones) can make all the difference when stepping up to a momentous occasion. Choosing the right dress shoes can make anyone's head spin. But the right pair can bring your outfit together and leave a lasting impression.

After all, when it comes to making a great first impression, you quite literally need to put your best foot forward—so why not make sure that foot is in the perfect pair of shoes? Whether you're dressing for a big meeting in the office or a gala fundraiser, understanding styles of men's dress shoes and when to wear them is essential.

In this guide to men's dress shoes, we'll explore classic styles, their best uses, and how to pair them with suits and accessories. And yes, let's not forget the importance of matching socks, which we'll also touch on to ensure every step you take radiates timeless style.

Oxford Shoes: The Definition of Elegance

George Frazier, midcentury Esquire magazine men's style pundit.

Any guide to men's dress shoes will include the Oxford. The Oxford shoe is the epitome of timeless style. You're safe in Oxford when people look down! Known for its closed lacing system, which creates a sleek silhouette, Oxfords are perfect for the office, formal events and weddings.

Black leather Oxfords are ideal for pairing with a black, navy, or charcoal suit, making them a staple for business settings or black-tie events.

Consider brown Oxfords in polished leather for a slightly less formal look. These pair beautifully with lighter grey suits or earthy tones.

Derby Shoes: Sophisticated Yet Versatile

For a more relaxed look, check out Derby shoes. They're a fantastic choice for office or casual settings. Black Derby shoes pair seamlessly with a navy or dark grey suit for a professional look, while brown Derbies can be worn with chinos or tweed blazers for a smart-casual vibe.

Derby shoes are also versatile across seasons, making them a go-to option for men who value flexibility in their wardrobe.

Monk Strap Shoes: A Statement of Confidence

Monk strap shoes, with their signature buckle closure, are a bold yet refined choice in our guide to men's dress shoes. Single or double-strap designs add personality to your outfit while remaining polished. Brown or tan monk straps are perfect for pairing with navy or grey suits for the office, while black options can be worn for more formal occasions.

These shoes are ideal for professionals who wish to exude confidence and individuality without being overly flashy. Their sleek profile also makes them easy to style with tailored trousers.

Loafers: Casual Meets Sophistication

"You have brains in your head. You have feet in your shoes. You can steer yourself in any direction you choose." - Theodor Seuss Geisel, a.k.a. Dr. Seuss.

Even Dr. Seuss knew the power of choice, and loafers are worth a second (or third) look when it comes to footwear. But there are times when loafers are not just an option but the perfect choice.

Loafers, particularly penny loafers, offer a stylish option for casual occasions. Their slip-on design makes them incredibly comfortable and easy to wear.

Choose leather loafers in shades of brown for a laid-back yet sophisticated look that pairs well with lighter suits, chinos, or even dark jeans. Grab a pair of suede loafers to add a touch of texture and seasonal flair for your next warm-weather event.

Chelsea Boots: Sleek and Modern

Chelsea boots are a versatile addition to any wardrobe. Their ankle-high design and elastic side panels create a streamlined silhouette, making them suitable for formal and casual outfits. Black leather Chelsea boots pair perfectly with slim-cut suits, while brown leather or suede options are ideal for offices that have a smart-casual dress code. Chelsea boots come in handy during colder months, offering style and practicality.

Brogues: Adding a Touch of Detail

You can spot brogues by their decorative perforations. You can get them in multiple styles, including Oxford and Derby versions. Brown brogues are versatile and pair well with navy or grey suits, adding personality to your outfit. Stick to black brogues for more formal occasions, and use them to complement tailored suits or blazers.

Full brogues (wingtips) add a statement to your outfit, while semi or quarter-brogues are more understated. We suggest taking the understated route. You don't want to draw too much attention to one part of your outfit.

Matching Colours and Materials: Polished Pairings

Pick colours and materials that complement your wardrobe staples to make the most of your dress shoes. Black leather shoes are the most formal and pair best with black, navy, and grey suits. Brown shoes are more versatile, working well with navy, tan, or earth-toned suits.

Any guide to men's dress shoes will include the importance of always matching your belt to your shoes. Brown leather shoes call for a brown belt, while black shoes require a matching black belt. But if you're feeling adventurous, pair a rich brown shade with black and see how the two elevate each other.

When it comes to socks, match them to your trousers for a seamless line or use them to add a pop of subtle colour. For more on sock etiquette, explore our article Dress Sock Etiquette: Elevate Your Style from the Ground Up.

Guide to Men's Dress Shoes: The Importance of Investing in Quality

Dress shoes are an investment in your style and comfort. Our guide to men's dress shoes wouldn't be complete without mentioning quality. High-quality shoes last longer and offer better support and a more refined appearance. Look for brands that use full-grain leather and prioritize craftsmanship. Well-maintained shoes will pay dividends, ensuring you always look polished and professional.

Step Confidently into Sophisticated Style

Choosing the right dress shoes is about more than completing your outfit—it's about enhancing your confidence and personal style. Whether you're slipping on the classic Oxford, the versatile Derby, or the bold Monk strap, each shoe style brings its unique flair to your wardrobe.

Remember the quote from Dr. Seuss; You have brains in your head. You have feet in your shoes? Armed with Aklasu products along with our articles and ebooks, you'll put both your brains and feet to good use while finding success in whatever you do.

Elegant dress shoes need sophisticated socks.