The Biggest Differences Between Styles Of Men’s Dress Shoes

If you want your next formal outfit to make a big positive impression, one thing is certain: you’ll need to pay attention to the details. Having a suit crafted from the finest materials is a great first step, but without nailing elements like fit and accessorization, even the most expensive garments can still look tacky or drab.

And when it comes to details, there’s perhaps no garment more important to get right than men’s dress shoes. Depending on the option you select, shoes can elevate the entire impression your outfit makes, or be a limiting factor that prevents you from achieving something truly great.

Fortunately, you don’t have to try to discern which dress shoes are the right fit on your own: so long as you stay within the major styles of men’s dress shoes, you shouldn’t have a hard time finding an option that looks amazing no matter your personal style.

That’s why this guide exists: in it, I’ll break down the major styles of dress shoes you’ll need to know about to build an outstanding formal outfit so that you can make the right decision every time.

The Icons: Oxfords, Derby Shoes & Loafers

When you typically think of “dress shoes”, one of these is probably the kind of shoe that comes most readily to mind. These types of shoe have become iconic for very good reasons, despite subtle differences between them: each of them features a simple and sleek leather body and is perfect for a wide variety of formal occasions.

As we’ve covered in a previous article, the difference between Oxford and Derby Shoes can be a little hard to discern. There are a few, but the primary difference is the “facing” (essentially, where the holes for your laces are located).

On an Oxford shoe, the facing will be discreetly tucked under the outermost body of the shoe, whereas Derby shoes feature the facing above the front of the shoe.

This might seem like a pretty minute difference, but it can make a huge difference with regard to the way the shoe interacts with the rest of your outfit. Oxfords give an impression that’s sleek and professional, whereas Derby shoes are slightly chunkier and more experimental.

Despite similarities between these two icons, discerning either of them from a loafer is relatively simple: loafers tend to be slip-on shoes without laces. Many loafers also feature a lower cut, creating an opportunity to show off some high quality socks.

So which should you wear? While any one of these shoes can be a great all-around choice for a dress shoe, I personally find that Derby shoes are a little more versatile than Oxfords and Loafers due to their versatility in a variety of fits and formality levels.

The New Classics: Wingtips & Monk Straps

If you’re looking to add something a little more off-the-beaten-path to accentuate your wardrobe, either one of these shoes is potentially an excellent option.


Especially for those with a passion for capital-M Menswear, Wingtips are becoming a widely loved staple due to their intricate and eye-catching pattern of perforations.

These intricate patterns can elevate otherwise minimalist dress shoes into veritable works of art. If you’re looking for a dress shoe that’s more on the formal side while also being highly expressive and exciting, these are a fantastic addition to nearly any wardrobe.

Monk Straps, on the other hand, are basically what you’d assume they might be from the name: the entire lacing system is completely removed in favor of one to two buckling straps. The result is a shoe that’s both unexpected and totally at-home in a wide variety of formal fits.

If you’re looking to breathe life into an understated, conservative look, these shoes are a perfect detail to add, especially in conjunction with other exciting details like complimentary pocket squares or watches.

The Boots: Chelseas & Chukkas

Maybe you’re looking for something a little more trendy and sleek rather than a more traditional dress shoe silhouette. Look no further: either one of these boot options will ensure you look up-to-date and totally dashing.


When I say “boots” in this context, I’m not referring to chunky wintertime snow boots, but sleek, sophisticated shoes with a higher profile made from the finest materials.

Chelsea boots, for example, are a longtime mainstay of my own personal wardrobe and find themselves at home in a wide variety of outfits. Chelsea boots are iconic for their low-profile, slim construction, featuring a discrete elastic band on the side rather than laces or buckles.

Paired with slimmer pants, Chelsea boots can create a sleek, slimming profile for your legs that makes the rest of your outfit even more impressive. Additionally, Chelseas can fit a variety of styles -- suede boots might be less formal than ones made from fine leather, for example.

Chukkas, on the other hand, are slightly more chunky and traditional. They’re essentially the Oxford approach to a boot, featuring a more durable sole but a similar construction and lacing style.

If you’re looking to embrace some modernity without looking totally out-of-place in more conservative dress settings, Chukka boots are built to embrace the compromise. Like Chelseas, these are also available in a wide variety of materials to fit many different styles and tastes.

Ultimately, whether your style is more on the conservative side or you love taking risks and being experimental with your fashion, a working knowledge of the major differences between styles of men’s dress shoes is a critical tool to build the outfits -- and the impressions -- that will make you look and feel your best.

There are a wide variety of options to select from, and no real wrong choices when choosing, with the exception of this one: more than almost anything else in your wardrobe, I highly recommend against trying to cut the cost of dress shoes.

As I said at the start of this guide, shoes are one of the key details that can make or break your outfit. Investing in premium quality materials and expert construction ensures that your shoes look and feel amazing as well as last for a long, long time.

If there’s one area to invest in your wardrobe above all others, it might just be this one.

Fortunately, Blaine’s carries plenty of outstanding mens’ dress shoes! Feel free to drop by Blaine’s website or visit our Montgomery location for some of the best men’s fashion that Cincinnati has to offer.