How To Make Dress Shoes As Comfortable As Possible?

Dress shoes, for men and women, can up your style quotient for all occasions, both formal and informal. Dress shoes have evolved differently from footwear for casual occasions and sports shoes. Sometimes, with dress shoes comfort can get sacrificed at the altar of elegance. If you’re planning to buy a pair of dress shoes, then read on to learn how to give yourself the best shot at buying a comfortable pair. If you’ve already bought a pair of dress shoes that’s not as comfortable as you’d want it to be, fret not. We’ve got some cool actionable hacks that you can easily implement to wear these shoes.

Factors that Influence Comfort in Dress Shoes

  • Dress shoes, particularly the ones meant for formal occasions, have stitched leather insoles that are not cushioned. The wearer may experience discomfort.
  • Footwear for formal wear is invariably constructed using stiff leather that does not flex easily, and if the shoes do not already fit snugly, then breaking into such shoes can be uncomfortable. Leather outsoles too hinder flexibility, at least in the beginning. Goodyear welted shoes offer a more robust construction, but it comes at the cost of flexibility. Breaking into these shoes can take upward of six months. Blake stitching provides better flexibility for moving the feet.
  • Thin leather soles not only wear out completely, they can also steadily erode the wearer’s confidence to walk on smooth surfaces, like on tiled flooring inside buildings. They do not provide the required cushioning for comfortable wearing for hours. The wearer’s feet may ache by the end of the day.

Do the Dress Shoes Fit?

That’s the first consideration. The shoes need to fit, and if you can get this aspect of buying dress shoes right you improve your chances at owning a comfortable pair that won’t be much trouble breaking into as your feet and the shoe try to get to know each other better. Get your feet measured before buying a pair. Of course, you will try the shoes and walk around a bit to get an idea of the degree of comfort in terms of undue pressure on the toes or tightness on the sides.

Custom-made shoes are your best bet for the most comfortable fit. However, bespoke shoes are expensive. Most of us are more likely to buy mass-produced dress shoes, of a make and from a brand that suits our feet, sense of style, and our wallets. When buying Oxford dress shoes with a closed lacing system, check if the shoes feel comfortable after the laces have been tied. Oxfords, designed with close-fitting quarters, are not as given to comfort as other designs.

With respect to fit, if the dress shoe feels tight when the laces are tied, it may be a good idea to try a wider shoe style of the same size instead of moving a size up. This is particularly recommended for those with flat feet. Or, move up half a size to check for a comfortable fit.

Dress shoes are constructed such that they flex at the ball of the foot. So, the fit of the shoe must be such that the balls of the feet do not feel constricted. Of course, you must give some allowance for the fact that the shoes will loosen with time.

The right way to shop for dress shoes is to first ensure as correct a measurement as possible. There are three things to be measured. These are the length from heel to toe, the arch length, and the width of the foot. A Brannock device lets you measure these effectively. Most shoe stores have this device, and using this is the first step to ensuring that you buy the most comfortable dress shoes.

Since, sizing conventions vary with the manufacturer, you may want to try out dress shoes by more than one brand to get a feel for the size. There is no skipping this part, you have to try on the shoes.

Tips to Make Men’s Dress Shoes Comfortable

  • Instep supports offer support to the feet, especially for people with low arches. The right-sized support will lift the feet and help fill out the shoe so that the wearer does not have to tie the laces too tight for a snug fit. Also known as insoles, these supports provide orthopedic support by spreading the weight of the foot over a larger area. Proper arch support is essential for people with flat feet or plantar fasciitis. Even otherwise, arch supporting shoes reduce stress on the heels and prevent foot aches.
  • If the shoes are too tight, then a shoe stretcher at the cobbler’s shop may help loosen them and may yield the desired level of comfort.
  • If the shoes chafe at the heels when walking, then heel grips are a nifty solution. These will keep the heels in place. Try on shoes with socks that you would normally wear to get an idea of the most appropriate fit.
  • Knowledge about the attributes of dress shoe styles helps. If, for instance, you’re planning to buy Chelsea boots, then select ones with a firm yet elastic panel over the ankles for improved comfort.
  • Dress shoes, particularly the aforementioned Chelsea boots, may chafe at the ankles. A heel lift can help eliminate the chafing.
  • With monk strap shoes, the buckle may stick uncomfortably into the side of the foot. Consider choosing a pair with double straps that are placed a little lower on the sides.
  • It’s a good idea to have a shoe horn at home; it helps slide the foot in without discomfort and prolong the life of the heel counter.
  • Use leather conditioners that can soften the hard leather so that the material begins to conform to the shape of the feet. Choose conditioners that are appropriate for the leather type, whether suede, calfskin, full grain, or nubuck.
  • Thin absorbent socks can make a big difference to the wearer’s comfort. They absorb perspiration, prevent chafing, and where required can add that little bit of cushioning to the feet for a snug fit so that the heel does not slip.
  • Resole shoes with rubber soles, if required, to ensure a firmer grip and better flexibility.
  • As compared to lace-less loafers and slip-ons, dress shoes with laces and buckles allow you to loosen or tighten them to adjust for small changes in fit because of thicker socks in winter or changes in the size of the feet as the day progresses.

Tips to Make Women’s Shoes More Comfortable

Women’s dress shoes too come with their own share of comfort-related issues. While braving a little discomfort in the feet for the sake of appearing elegant at evening soirees is not unheard of, it is avoidable. Here’s how.

  • When purchasing dress shoes, consider doing so at the end of the day when the foot is at its largest. Yes, it’s an anatomical fact. Feet expand a bit from standing and walking. The fit of the shoe on the larger foot is a fair measure of the size that is ideal for you.
  • The construction of the shoe, particularly ballet flats, should be such that any flex produced during walking does not result in gaping loss of shape.
  • Flat-heeled shoes with an elastic topline will prevent the shoe heel from slipping.
  • If you’ve purchased 5-inch heels but are finding that walking in them is a tad too uncomfortable for you, then carry the stilettos to the cobbler to have an inch or two shaved off. What you may lose in height, you will gain in comfort.
  • Sometimes, all you need to do to feel comfortable walking in a pair of heels is to squeeze in the abs and place your weight first on the heel and then on the toes.
  • You probably already know that platform heels are more comfortable than regular heels; it’s something worth remembering the next time you want to add a pair of heeled dress shoes to your wardrobe.
  • Consider using heel grips on strapless shoes if you’ve got narrow feet and you’re not too sure about walking because you can feel your feet sliding around in the shoes.
  • Thin insoles inside open-top sandals can provide your feet with just the right amount of lift for comfort and balance.
  • Know the shape of your foot and purchase shoes that will be kind to your feet. If you have flat feet, then heels above three inches high will hurt the feet.
  • Stiletto heels present difficulties in walking, especially on soft earth. Attaching protectors on the heel tips can increase the surface area of the heels, add to comfort when walking and also minimize the chance of injury.
  • The level of comfort desired also varies with the occasion. So, if you’re going to be on your feet all day wearing dress shoes, then you may want to consider low pumps or brogues. For a wedding, you can choose heels with ankle straps and if the shoes cause discomfort from friction that cannot be allayed with insoles because of the strappy design and narrow profile of the shoes, the consider using a lotion to ease the friction.
Sarah Shawman

is the webmistress of Footwear 4 Workers.

She started this website out of displeasure with the fact that there are so few good online resources especially dedicated to the 99%: working people. Having suffered from work related plantar fasciitis herself, she set out on a mission to help others.

She updated this page on and will continue to update it as time goes on.

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