How To Break In Your Dress Shoes

Dress shoes such as Oxfords, Derbies and brogues are normally made from leather. There are imitation leather dress shoes made from other materials which will need to be broken in too. However, these shoes will not mold to the shape of your feet in the same way that a leather shoe can.

Lots of things affect how comfortable dress shoes are. Does your brogue have a rubber sole or leather sole? Do you have especially long toes or flatter arches? Shouldn’t the shoe be comfortable right from the start?

Snug From The Start 

There are two schools of thought when it comes to choosing the right size and fit of shoe. You do not want to choose a size that is too small and will rub on your toes, but a roomier shoe will also be a problem as, in time, it will stretch.

Generally, you are advised to make sure that the shoe is ‘snug’ on your foot. In fact, there are also cultural differences when it comes to how well a shoe should fit you. Europeans prefer a tighter fitting dress shoe, while Americans and the English prefer a looser fit.

When you are looking at various styles of shoes and buying shoes from Europe or Britain, you must remember that the fit may be quite different. Because of this, it’s important to consider the kind of fit you prefer and work from there.

This is going to dictate not only where your shoes are made but also the kind of fit they will end up having once they have been properly worn in. While you’re shopping for shoes, make sure you take a look at where they were made. Also, take into account whether they trend towards being true to size or have a larger or smaller fit.

Dress Shoes Are Designed For Style And Comfort

Dress shoes like Oxfords and brogues are generally highly engineered and designed to be comfortable to wear. However, there are different shaped tips: rounded, more square or pointy. You need to choose a style that suits your foot shape too.

Something that is important to consider here is whether or not you have wider feet, as that can change the options that are available to you. Furthermore, it’s wise to consider the kinds of outfits you plan on wearing with the shoes so that you can get something with the right style.

Extreme Ways To Stretch Leather Shoes

Generally speaking, you have probably spent a lot of money on your shoes, so you should probably avoid the ‘extreme’ methods of making your shoes more comfortable. Unless your shoes are far too small, stretching them will be permanent and could ruin them.

It’s typically much better to choose shoes with a much closer fit to your foot. That way they can stretch into shape through normal wear without being too uncomfortable. If you need to, try out a few different size options to ensure you get the best possible fit.

Stretching with Ice in the Freezer

Placing bags of water into your shoes and then placing them into the freezer overnight is one way to stretch your shoes out. The water will freeze, and the ice expands.

In the morning your shoes will be stretched out. However, the leather will probably be dried out too, and will have water damage.

While there might be some rare instances in which this method might work, it’s generally not a good idea because of the damage it can cause. If you do try it, keep in mind that your shoes may be damaged afterward. It may be better to return or replace the shoes with something that offers a better fit instead of trying this.

Heating with a Hairdryer

Another way to stretch out the leather is to apply high heat. If you heat up the leather while wearing the shoes, they will stretch out and fit better. However, once again, you are stretching and damaging the leather by applying heat. This will be permanent and your shoes will also stretch during the normal process of wearing.

Like the freezing method, you will need to realize that your shoes could be irreparably damaged by this method. They also run the risk of ending up too loose if you adjust them to the perfect fit and then continue to wear them in.

Breaking In Your Shoes The Sensible Way

Don’t wear your new shoes for the whole day. Instead, wear them at home first, or for shorter trips. You could also take along a second pair of shoes. Over time, your dress shoes will stretch, and mold to the shape of your foot. This process can take a few weeks, but the leather will soften and your dress shoe will become more flexible.

Wear socks but remember that leather is a natural material that will not magically stretch back. You can manually manipulate the leather where it is hurting you, such as ‘riding your ankle’ or pinching your toes. You can also wear cushioned plasters if you have developed blisters.

Placing a shoe shaper into your dress shoes overnight will help break in new shoes. Or you could take your shoes to a specialist and have your shoes professionally stretched. Stuffing socks and newspaper into your shoes can also help to soften up the shoe.

These methods are generally much better as they offer a more natural way to stretch the shoes into shape. A professional will also be able to make the needed changes with a much lower risk of causing permanent damage to the shoes themselves.

Have You Chosen The Right Size or Fit?

The best way for you to break your shoes in is to wear them. Slowly, over time, the shoe will mold to your feet. However, if your dress shoes are still hurting you, then you need to look carefully at the fit and size. If your arches are too low, you can consider adding arch supports or an inner sole to your shoe.

Your foot may be slipping too much inside the shoe or running on the shoe. Similarly, if your foot is just too wide for the style of a dress shoe that you have chosen, it will continue to be painful to wear and will not support your foot correctly.

Your mobility will be hampered, and ‘breaking’ your shoe in may damage to your tendons and nerves. If this is the case, then you simply need to choose a different style and size and start again.

When it comes to the fit of your shoe, it’s not generally a good idea to “tough it out” as your feet can be damaged. It’s far better to take your time and select a shoe that you can wear in while still being relatively comfortable.

The Spritz Fix

All quick fixes will work, but you will need to be cautious. Is the whole shoe too tight or is just a specific part causing discomfort? You can make a solution of rubbing alcohol and water and rub it into the inside of your shoes. Place your shoes on your feet immediately and wear them.

This will help the shoe to mold to the shape of your foot. With any quick-fix solution, you need to be sensible. If you don’t have much time and are desperate to alter the fit of your shoe, then go ahead.

However, leather does stretch and applying a lot of leather conditioning products may be a better idea. Softening the leather is probably a better way to make your dress shoe easier to wear if you are in a crunch. You may also crack the leather if you bend your dress shoes too much.

If you’re considering a method like this, make sure to take into consideration how long you’ll need to deal with the discomfort in the shoe. If it isn’t long and you’ll be able to find an easier option later in the comfort of your home, that is generally a better option.

Breaking In Your Dress Shoes

The best way to break in your new shoes successfully is to do it slowly. It will probably take about 4 weeks and yes, you will have to suffer a little. However, there are a number of products and methods you can use to be more comfortable.

Keep in mind that while a little discomfort can be expected, you shouldn’t be in extreme pain. When you aren’t wearing the shoe, wooden shoe stretchers can also help to get them into the right fit. Be sure to wear socks and plasters (if necessary) during this time.

Remember also that you shouldn’t wear your dress shoes for a full day at first, but rather in shorter bursts. You will be rewarded with a well fitting dress shoe which has molded to your foot and will be very comfortable to wear.

A quick re-cap on the best way to break in those new shoes

So we’ve already discussed and established some tried and tested, centuries-old techniques for breaking in those new shoes. After all, you have invested in a pair of quality shoes, designed to last so you your pain will ultimately be rewarded when you are the proud owner of a pair of shoes that have very much been crafted to last and that will eventually fit you like a glove. So much so in fact, that they are going to feel more like slippers than shoes.

While that might seem like a strange analogy today, trust us, your shoes will most definitely stand you in good stead down the line with any painful pinching or discomfort but a fleeting memory. So the real moral here is not to get disheartened and remember that while you might have to break your shoes in gently at first until your feet fit them like a glove, pretty soon that is exactly what they are going to feel like.

Wear them around the house regularly

Don’t delay, go right now and grab your shiny new shoes from out of their box, pop them on your feet and have another ten minutes just wearing them around the house while you get on with a few extra chores. Walk up and down the stairs for example; even wear them while you are preparing dinner this evening. The point is, get used to how they feel on your feet while you are indoors, standing around and sitting down.

As we already discussed, the watchwords when breaking in a new pair of shoes are really, little and often. Don’t feel that you have to wear them for hours at a time. They may have felt initially comfortable in the shop and they will soon feel totally part of you too with some time and effort. So just to recap, we recommend regularly wearing them for say 10 minutes at a time to get you started.

Take them into the office with you to give them another trial run

Why don’t you try taking your new shoes along with you, but only wearing them sporadically at work for example? That way you know you can travel back and forth from home in your more comfortable, well broken in shoes while effectively giving your new ones a bit of a trial run so to speak.

If all else fails, head to a professional

If that is all taking too much time and quite frankly, you just love your new shoes and you want to get down to the business of actually wearing them properly, then as a final option, you could just head back into your local cobbler. Forget the heat and cold remedies, filling your shoes with ice packs or even potatoes. Instead, hand them over to the professionals and they will have you skipping with joy out of the shop for probably less than a decent pair of dress socks will cost you. They should be able to machine stretch the shoes to your exact specifications and after just a couple of hours drying time later, it will be like you and your new dress shoes have always been together.


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