How To Make Men’s Dress Shoes Comfortable

(This guide is strictly for men's dress shoes. If you're looking for a good resource for women, visit our women's shoe size guide or our general footwear guide on how to make shoes more comfortable)

We’ve put together a list of the best hacks to make ready-to-wear men’s dress shoes in particular, more comfortable. Our comfort kits requirements are just guidelines to help you make the most of your footwear- feel free to interchange elements to suit your needs.

The most pronounced difference between dress shoes and everyday footwear is simply that most dress shoes are created with (sometimes) rigid leathers. They’re almost always classic in style and fit and you’d be walking on a leather sole which is most often, not very comfortable.

When it comes to classic dress shoes, fit is vital for comfort. Fit comes from firstly making sure that the size you buy is the right one.


Fit first

Follow our guide on how to tell if your shoes fit.

Like with clothing, footwear has fitting standards that it needs to adhere to. However, just as clothing sizes are merely a guideline- a cookie cutter standard that is most certainly not a ‘one size fits all’ solution to perfect fit. Our first piece of advice when discussing any issue around comfort and shoes is to have your feet measured. Feet change; with age, illness, lifestyle changes, pregnancy etc. Having your feet measured at least once every six months is a good idea to keep on top of any changes your feet are going through.

Shoe Cobler

The most perfectly comfortable pair of dress shoes can most definitely be found by going the bespoke route. Google bespoke shoemakers in your area and your experience might look a little like this: PIC

Your foot will be measured the traditional way with a tape measure, the shoemaker will then create a ‘last’ or foot mold representative of your foot shape (quirks included). The shoemaker then makes a shoe up in your desired style out of cheap material to test the fit- once you fit this primary prototype, any fit changes will be taken into account and your final shoe in the selected high-quality leathers you choose. Bespoke shoes feel and fit better with each wear as each shoe, left and right is unique to your feet, warts and all. That being said, the bespoke experience is an investment and can be an expensive treat when you’re ready to spoil yourself.



Tips for specific dress shoe types


Men’s Oxfords

mens oxford shoes

via grenson

Whilst they’re the go-to choice for the snappiest dressers, they’re not the most forgiving in terms of comfort because the ‘quarters’ (that’s the bit that has the eyelets and lacing) actually doesn’t open fully and is sewn under the toe bit of the shoe.

Top Tip: if, during fitting, the lacing system hurts or is too tight over your arch- go for a wider fit and not a size up. If you can feel the eyelets, choose a better designed style where the tongue prevents the eyelets from touching the foot.


Comfort Kit Requirements


Comfort grips Silicone Strips Ziploc Bag


  • Heel grips: Keeping the heel steady in the shoe will prevent repetitive chafing and blisters at the back of the shoe. Make sure you purchase a heel grip with a soft suede feel.
  • Silicone Strips: Sometimes, the seam that runs across the width of the shoe can bite into the top of the foot- laying a thin silicone strip over this place can offer some respite from the bite.
  • Insoles:Whether you have a flat foot or just like to have the extra cushioning, insoles are your go-to hack for making any style of footwear feel great on your feet. Investing in custom insoles is as seamless as using the FitMyFoot app to order a pair in minutes.
  • Ziploc Bags: If your shoes are still somewhat too tight on the foot, fill a ziploc bag halfway with water, insert into your shoes and pop into the freezer, as the water freezes, it will expand your shoe- you will be able to get a good stretch in the arch height of your shoes this way.


Men’s Derby’s

mens derby shoes

These, unlike Oxfords, are a little more forgiving in terms of fit because the ‘quarters’ are sewn on top of the whole shoe and can open all the way to expand somewhat and give you a little more space over the arch when tied loosely.

Top Tip:Sometimes, wearing thin bamboo socks with a shoe that is just the right size but a teensy bit too tight does the trick by protecting your foot without adding any bulk- bamboo has the added benefit of being pretty absorbent.



Comfort Kit Requirements


foot weith arch support shoe stretcher Spray bottle with shoe stretching serum



  • Instep Supports: Derby’s are not always the best choice for people with low arches- wearing a good, supportive molded insert can lift your foot toward the throat of the shoe and will prevent you from needing to choke the laces to keep the shoe on.
  • Shoe Stretcher: If your problem is the opposite to the above, then either take the shoes to a cobbler to stretch or buy a shoe-stretcher to use at home- or try out a DIY shoe stretching serum:
  • Shoe Stretching Serum: Equal parts rubbing alcohol and water, first test out the alcohol on an inconspicuous part of the shoe to make sure that it will not stain your shoe. Pour solution into a spray bottle and spray your shoe, until it’s damp, wear them until the alcohol dries and then treat your shoe with a good leather conditioner after that.



Men’s Chelsea Boots

Chelsea Boots

This laid back classic style sometimes also known as the Beatles Boot, made popular by its namesake has been around since the 1800’s. They’re often the choice for people who prefer not to have to fuss with laces but still want a classy look and as a bonus, they’re easy to put on and pull off.

Top Tip: Always choose Chelsea boots that have the elastic panel stretching over the ankle- it makes for a super comfortable walk.



Comfort Kit Requirements


hair dryer and socks arch support heel lifts



  • Socks and a hairdryer: This type of shoe can sometimes run a bit tight over the girth of the foot. If you’ve sized wider and the length size works but the fit is a bit tight- wear thick socks, put the shoes on and then heat it with the hairdryer for about 15-20 minutes until the leather is soft and continue to wear it until the leather cools down.
  • Arch Support:Sticking in a bit of padding at the arch will lift your plantar up off the insole of the boot and add a layer of comfort.
  • Heel lift:If you find that your ankle chafes against the leather, add a heel insert/heel lift to lift your ankle out of the chafe zone.



Men’s Monk Strap Shoes

Monk strap shoes

Known as the classy man’s shoe, this buckled style has been reinvented and redesigned to sometimes feature two buckles. Whilst the purpose of the buckles is to keep the shoe firmly on your foot, some Mediterranean men wear theirs partially unbuckled for a casual kind of nonchalance.

Top Tip:If you feel the buckle biting into the top or side of your foot when wear-testing these shoes in store, try a style that has either the two buckles or look for a different style that features a buckle that’s placed lower.



Comfort Kit Requirements


Shoe Horn Thick Socks


  • Shoe Horn:This style is always a bit of a squeeze to get into. A shoe horn will get your foot in easily without damaging the heel counter of your shoe.
  • Thick Socks: This is a hardy styled shoe and requires some wearing in. Gently stretch out your shoes by wearing thick (or double) socks until they feel just right.



Men’s Penny Loafers

penny loafers

This Norwegian farmer’s staple made it’s way onto the fashion scene around the 1930’s and was given this moniker because the leather pocket on the top of the shoe was the perfect size to hold a penny. It’s by far one of the most comfortable classic styles. Today, the styling of loafers ranges from sleek classic lines to trendier stitching and patinas and most don’t really feature the pocket that gave it its’ name.

The most common complaint when wearing loafers is the heel slipping off when walking- solve this by investing in customised insoles from FitMyFoot and pairing that with a heel grip to hold the back of the shoe firmly to your foot.



Comfort Kit Requirements


Heel Grips


  • Insoles:No matter whether you fit wide or narrow, this style of shoe really does benefit from the addition of a padded, molded insole. A good quality one will absorb perspiration and keep your feet from feeling fatigued.
  • Heel Grips:For men with narrow heels, a padded heel grip will keep the shoe on your foot without you needing to scrunch your toes for that.

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