Best Comfortable Elevator Dress Shoes for Men

Best Comfortable Elevator Dress Shoes for Men

Dress shoes may never feel as comfortable as your favorite pair of slippers, but that doesn't mean they can't be comfortable at all.

At, we've put a lot of thought into comfort. For more than 20 years, we've studied the signature details of traditional shoe styles and learned to hide height-increasing insoles and lifts inside. We've made sure to make those lifts and insoles comfortable and stable, so in many cases, our dress Elevator Shoes are more comfortable that what you'd find at a shoe store.

But certain characteristics of dress shoes can make them even more comfortable.

We've picked out some of the most comfortable men's dress shoes here and placed a special emphasis on things that help add comfort. Feel is part of the package, after all - you'll love the boost in confidence you feel when you first put them on, and by staying fresh on your feet, that confidence will last as long as you want.

So take some notes and look for these attributes in comfortable dress shoes for men while you shop.

Perks of Derby shoes. The difference between Oxfords and Derbies is important for comfort: A pair of Derby dress shoes features two separate panels for the laces that go over the vamp, or tongue. This has an effect similar to how athletic socks grip the center of your foot. These CALTO leather dress shoes show that a Derby can be just as elegant as an Oxford.

Microperforated panels. Look at the sides of these CALTO Leather Derbies. The microperforated leather adds a dimension of refinement to the apperance, but also allows just a bit of extra breathing. That keeps your feet more dry and fresh.

Lightweight shoes. These CALTO dress Oxfords look sharp, but their lighter weight means your feet don't work as hard. Part of the reason sneakers are comfy is because of their light weight, after all.

Slip-ons and loafers. While loafers are clas">CALTO beauties. Part of the reason Oxfords are elegant has to do with the open face, and slip-ons offer an even more open look.

Dress boots exist. From these CALTO Chelsea boots to zippered or laced options, dress boots can have the same designs and Oxfords. The taller ankle height can also allow for bigger boosts in height - they are a good option for gentlemen seeking a boost as high as four inches.

Square toes. The cut of a square toe can look just as chiseled and elegant as a pointy one - study these CALDEN leather dress shoes to see what we mean. The horizontal space inside allows some extra room for your toes, however. That has the added bonus of enhancing your balance, so if dancing is in your future, a square toe may be a nice option.

Puff toes. These help traditional patent leather dress shoes such as these TOTO tuxedo shoes look just as refined, but the extra vertical space goes a long way toward comfort.

Now that you know what to look for, browse our large line of elevator dress shoes to find something that combines comfort and style. Whether you're planning for a day at work or a night on the town, you'll find something that increases your height, boosts your confidence and keeps you on your toes.


Back to blog

Leave a comment

Please note, comments need to be approved before they are published.

Subscribe to our newsletter

Be the first to know about new collections and exclusive offers.