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Men's Dress Shoes Guide 

They say a man’s shoes is what everyone notices first. Men who wear nice shoes (most middle management, executives and c-suite employees) will judge another man by the shoes he is wearing. It's just like sizing someone up...although you probably won't be fighting.


You should be wearing nice shoes that you regularly care for; they will last you decades and don’t’ have to break the bank. In a dressier environment, leather soles on the shoes is the norm and any other soles might be viewed negatively. Rubber soles can be acceptable, generally if the thickness of the rubber sole matches what it would be on a leather sole (see example image to the right and click here to check out my post on Dainite Rubber Soles).


Based on the market price right now for nice dress shoes, $200 is basically the minimum to purchase a great dress shoe, so start saving! There are definitely sales that will bring that down, but a $200 pair of nice shoes will pay for themselves. You can repair the soles of the shoes for around $40 at your local shoe repair shop. I bought my first pair of Allen Edmond last year and they are two times nicer than the Cole Haan I own, and also two times more expensive.


Care for your shoes and they will continue to repay you over decades. Own shoe creams, brushes and moisturizers.


Avoid very square toe, clunky dress shoes. They are clear indicators of ‘not so good’ fashion decisions.


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Allen Edmonds Strandmok


Recommended to Start

Buy a pair of dark brown, captoe or wingtip, oxford shoes with leather soles. From there, perhaps pick up a pair of tan shoes. Mix up the style and go with either lace ups or loafers. Then expand elsewhere. Consider a tan pair of wingtips or a statement shoe of sorts. Bring it out maybe once a week or on nice weather days. Keep in mind people will definitely notice a nice statement shoe!


Don’t forget to buy a new belt that is a similar color to your shoes!


Money is saved in the long run by investing in a good quality shoe that will last decades. Sure, it costs more money upfront, but you’ll own the shoe forever!


Recommended to Start

The most basic shoes to own are a dark brown pair of oxford and a black pair of oxfords. Mix up the styles though: if you own plain black oxford lace ups perhaps go with a wingtip brown lace up or a brown loafer. Loafers are definitely acceptable with suits, although not as ‘dressy’ as an oxford shoe with a suit.


Once you have the basics, branch out to a tan pair or a shoe that catches a little more attention. Perhaps loafers with tassels or a pair of double monk straps. Don’t wear your ‘statement shoe’ every day, since they are more noticeable.


Allen Edmond Strand Dress Shoe
Cole Haan Dress Shoes Brown Bit Loafer

Eredita Loafers

OSK Custom Monks

As mentioned above, leather sole shoes are the only shoes to own in some work environments. A quality pair of shoes will have a quality leather sole that will last awhile. The shoe will also most likely be a Goodyear welt construction.  


In some instances, a pair of rubber sole dress shoes is necessary for extreme weather. Ensure the thickness of the rubber sole is not noticeable and equal to the width of a leather sole shoe. Click here to check out my post on Allen Edmonds Dainite rubber soles. 


I recommend buying a pair of galoshes. They’re great for wearing to and from the office, especially if you are taking public transportation. I leave them in my car when I’m meeting with clients and just wipe off my shoes with a very lightly damp cloth when I get home.


To reiterate a prior point: avoid a very square toe, clunky dress shoe. Read any article about the shoes not to buy and these are first on the list. Don’t be “that guy” in the office.


Basic Shoe Care

Do as your father probably did. Get an old shoe box, some old undershirts and start buying up shoe care products. The most basic and versatile product is a simple moisturizer.  You can pretty much use it on any leather shoe and you don’t have to worry about color. It won’t give you the highest shine, but it will clean the shoe and condition the leather.


Shoe creams are the way to go over wax based polished or oils. Everywhere I have read eventually all point to the shoe creams. Creams will condition the shoe and provide a nice shine. Other products (mink oils, saddle soaps, wax-based polished, etc.) can dry out and damage the leather if they are not used properly.


Basic Shoe Care

Most websites will tell you to clean your shoes once a week and it’s a sin not to! Realistically, every couple weeks should do your shoes justice.


Taking care of your shoes really does make all the difference for the longevity of the shoe. Nice shoes just start breaking in after a couple years (okay maybe a slight exaggeration, but they’re seriously comfortable)! Permanent damage can happen to the leather if they are not cared for.


Get cedar shoe trees and put them in your shoes right after you take them off of your feet. Shoe trees should be put into the shoe within several minutes of taking them off. This holds the leathers shape and also provides mild odor absorption. It is probably worth it to have one per really nice pair of shoes and rotate another set through shoes as you wear them.


As soon as possible, wipe the salt off the shoe in the winter (very lightly damp cloth) and stuff them with newspaper if they are damp. Never put them in front of any direct heat source, this will permanently damage the leather.


If your socks are getting wet in your leather soled shoes, then you need to invest in a Goodyear welt shoe. This will solve the problem.


Investing in a nicer pair of shoes allows the soles and heels to be repaired for much less than the cost of a new pair of shoes. The local cobbler will probably use a much higher grade leather sole than what comes standard on most shoes (I have noticed this on the past three Cole Haan shoes I had repaired).


Basic Shoe Care Essentials for Young Professional

Basic Shoe Care

Recommendation Links:

Cedar shoe trees

Shoe horn

Shoe cream kit

Brands and Price Points

There are a lot of great shoes out there for around $200. I would definitely stick with the shoe brands that actually make shoes (e.g. not Banana Republic or J. Crew branded shoes). You are just paying more money for their name put on another brands great product.


Just keep in mind that you are paying for quality, comfort and longevity.


Allen Edmond shoes are some of the highest quality dress shoes on the market and they can be found at a reasonable price. The brand is about as American as you can get. AE shoes are made on a lot of different lasts (molds), so a size 10 in one style might not fit the same as a size 10 in another style. They are hard to find on sale, but when you do and the shoe fits, buy them.

Allen Edmonds Strand (highly recommend)

Allen Edmonds Double Monk 

Allen Edmonds Dainite Rubber Sole


I’ve contemplated whether or not I even want to share this secret, but I will. . You’re welcome.


Brands and Price Points

Cole Haan shoes are great for a solid pair of stylish shoes at a reasonable cost. You can often find these on sale for around $120. Be cautious though, there is a wide variety of quality on their shoes. Just because they are Cole Haan doesn’t mean your boss won’t think they’re ugly.

Cole Haan loafers 

Cole Haan Wingtips 

Dursen makes a fantastic dress shoe for a great place! This is a boutique brand and really focuses on quality and customer service. I highly recommend this shoe above other brands in the $100 price point.

To Boot New York is a great brand that is typically rubber soled. This is a good brand to reference for an example of what a nice rubber sole should look like.

To Boot New York double monk

Magnanni is another great brand in the same price point as well.

Magnanni shoe

Mezlan seems to be nice quality as well, similar to the others mentioned.

Mezlan loafer

Frye shoes are really nice if you are looking for something in between casual and dressy. The quality is top notch and the selection is very broad.

Frye rugged loafer

Bass shoes can often be found for ridiculous deals at their outlet. I personally don’t think the quality is that great, but their style is generally on point and you can get them for a very reasonable price.

Bass loafer


Bostonian I have personally had trouble with the quality of the leather. I have noticed it doesn't breathe as well. They are good starter shoes though!

Sebgao makes a great loafer if you're looking for somthing super casual

Sebago loafer

​Johnston and Murphy is a classic shoe brand and can be found on sale for fairly resonably prices. 

Johnston & Murphy Derby


***All Photos and Content By Dapper Professional



Cole Haan Wingtip Brown Chukka Shoe

Cole Haan - Wingtip Chukka

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