The Most Comfortable Dress Shoes On Zappos

1. Bruno Magli Butler Cap-Toe Oxford

It would have been disingenuous to start off this list of comfortable dress shoes without what is perhaps the most popular style of formal shoe, the cap toe oxford. As our top choice, we’ve gone for the made-in-Italy Bruno Magli Butler bal oxford for a number of reasons.

First of all, the soft calf leather will ensure the upper molds to the silhouette of your foot after only a couple of wears. Couple that with the premium cognac-toned Italian leather and genuine hand-burnishing, and you get a classic style in a handsome presentation. We prefer the cognac though black calfskin is also an option if you’re looking to stay as formal as possible.

Perhaps most importantly, the Butler oxford employs an Extralite rubber (EVA) outsole that is not only extremely lightweight but also incredibly durable thanks to its ago construction.

2. Allen Edmonds Chromexcel Strandmok

If you’ve browsed your way through a couple of our most popular shoe guides, you’ve probably realized that we’re big fans of the Allen Edmonds brand as a whole. More specifically, the Strandmok style is without a doubt one of our favorites.

While brogues tend to be considered a bit less formal due to their trademark decorations, we think that employing refined leather for the upper such as Chromexcel easily moves these into the formal realm, especially considering that these shoes boast traditional 360-degree Bench Welt construction. The leather choice, along with the precise pinking, medallions, and perforations, also give the shoes a subtle antique or distressed vibe that is indubitably formal.

To ensure comfort, these Chromexcel Strandmoks also possess a CustomCork insole that ensures a custom fit to your individual foot shape, as does Allen Edmonds wide-ranging shoe size and width options. And if these turn out to be the best shoes you’ve ever worn, you can rest easy knowing they can be resoled down the line.

3. Salvatore Ferragamo Scarlet Loafer

There may not be a more iconic Salvatore Ferragamo shoe style than the bit loafer, particularly the “Double Gancio” style that mirrors the buckle on their world-famous belts. As with the Strandmoks above, with a loafer shoe, you could be looking at a more casual style, however, the leather choice and overall execution produce an absolutely premium shoe that is nothing short of elegant.

The Scarlet Loafer possesses a soft, textured leather upper, leather lining, lightly padded footbed, and minimally stacked heel. Its almond-shaped toe ensures your foot has plenty of room while still remaining a classic silhouette.

Overall, the low weight of this loafer coupled with the convenience of it being a slip-on style and its absolutely stunning design make it one of our personal favorite shoes on this list. We’ve considered the price point in placing it at this position and have also included other more affordable options below.

4. Salvatore Ferragamo Recly Loafer

You’re not seeing double – we have indeed included a second loafer option from Salvatore Ferragamo on our list of comfortable dress shoes.

While we find the iconic Scarlet Loafer an outstanding shoe, we understand that not all individuals are partial to the bit loafer style. With this Recly Loafer, you get the same premium construction and materials in a more traditional style – the penny loafer.

Like the Scarlet Bit Loafer, the Recly Loafer boasts an unstructured Italian leather upper, leather lining, cushioned footbed, rubber heel strike, and durable leather innersole. We’ve also gone for an attractive walnut leather tone that Salvatore Ferragamo refers to as “Radica”. Whatever you want to call it, we’ll just call it beautiful.

5. John Varvatos Waverly Chelsea Boot

At position five, we arrive at our first boot style on this list of the most comfortable dress shoes. And yes, dress boots can be comfortable! You simply have to find the right ones, and we think these John Varvatos Waverly Chelseas fit the requirements. Let’s explore…

For a pair of boots to be comfortable, you’re first going to want to go for a slimmer silhouette that reduces weight; the Chelsea style undoubtedly fulfills this. Next, you need buttery soft leather and interior leather lining that permits all-day wear; the Waverlys are right there with these needs as well. Lastly, you need to ensure the insole and outsole also lend themselves to comfortable wear. With their rubber and cork sole blend, the Waverlys complete the list of requirements.

Of course, these being classically-designed Chelsea boots, the Waverlys possess the elastic panels that permit you to slip them on easily. Yet, in this expression, the panels have been “hidden” under the premium leather to conserve the formal shoe protocol.

6. Johnston & Murphy Sayer Cap Toe Double Monk

Deeper into this list we expand our selection to include styles that are not only more affordable but also slightly more versatile, so that you may dress them up or down depending on the occasion.

The Johnston & Murphy Sayer Double Monks crafted of a lustrous Mahogany Italian Calfskin are a great choice. The decorations on the cap-toe and the upper are subdued enough to be noticeable but not overly so. Likewise, the low stacked heel and leather outsole up the formality of the style, but comfort is not sacrificed as a foam-cushioned, leather-covered footbed will separate your feet from the ground wherever you walk.

Do not let the price point of the Sayer Double Monk (when compared to the previous selections) confuse you – this is an excellent pair of shoes with superior construction built to last for years.

7. Magnanni Ronin II

Nearing the end of this list, we land upon another loafer style. This should come as no surprise as loafers are some of the most comfortable styles of shoes that a man can count on in his repertoire.

The Magnanni Ronin II are available in a number of different materials, though we’ve settled on the grey suede variety. If you’re looking for a single pair of dress shoes, consider more traditional leathers such as calfskin, but we simply found this suede irresistible.

As the previous loafer selections, the Ronin IIs have a “saddle” with a minimal metal component. There are also stitching details throughout the vamp and toe box along with a burnished apron toe. With comfort in mind, this slip-on Ronin employs a lightweight rubber sole, leather lining, and leather insole.

8. Johnston & Murphy Conard Dress Cap Toe

For our value choice on this list, once more we look towards Johnston & Murphy, a brand that is not only known for high-end men’s styles but also affordable dress options that offer higher quality than competitors.

With the Conard Dress Oxfords, few cessations are made when designing this brogue style. It still possesses the attractive broguing details we saw in more expensive shoes from our list. The leather upper is hand-burnished, the inside is lined with leather, and the footbed is cushioned for comfort. Lastly the sole, of durable Boldwelt construction, has been painted to add a pop of color that imparts an attractive personality to an otherwise traditionally dressy style.