How-to Guides

Guide to Men’s Dress Shoes – What shoes should you wear?

If you’ve never bought a pair of men’s dress shoes, you’ll be surprised at how many different styles and colors there are to choose from.

The best all-around dress shoe to buy is a pair of plain black oxfords.  These lace-up suit shoes can be worn to interviews, to the office, to weddings, and funerals.  They are far from ornate or flashy and blend well with almost any suit.

Get More Than One Pair

Just because black oxfords are your best all-around option, this doesn’t mean you should pigeon-hole yourself into just one pair of men’s dress shoes.

Shoes should be rotated each day so that they can air out for at least 24 hours between wears. Besides, there are many styles and color variations to choose from and it’s a good idea to own more than one pair.

Before we get too detailed, you should know that each style of men’s dress shoes can be broken up into two categories.

These are the slip-on shoe and the lace-up shoe. Lace-up shoes can be tied in a balmoral style and a blutcher style. Blutchers are open faced and balmoral use V type lacing.


Color Coordinating Mens Dress Shoes

Black – The black shoe is the most versatile and can go with virtually any color suit you have.  This is the first color shoe you should buy.

Brown/Burgandy – Most suits will also accept this color with the exception of a black suit. The darker the shade the more formal the shoe.  If you want to get real daring, you could even go with a chestnut colored shoe.

mens dress shoes guide

Mens Shoe Styles

Brogues – A brogue is a pattern created by punching holes into the shoe. Brogues can be half brogue, full brogue, or medallion brogue. The first two are almost self explanatory.

Full brogues will have a pattern running throughout while half brogues will have the pattern running through half of the shoe.  A shoe is considered to have a medallion brogue pattern when the brogue pattern is all around the toe of the shoe.

Buck Oxfords – A buck oxford is a more casual shoe which is not made from the traditional leather. Wear this on casual Friday or to a dress down occasion.  I’d recommend putting this further down on your list of dress shoes to buy.

Cap-Toe Oxfords – Cap-toe Oxfords are dress shoes with a toe that is sectioned off with a separate leather portion. These shoes are dressy enough for the office but not for a formal occasion.

Chukkas – Chukkas are dress boots used in both formal and informal situations.  Look around your office and use your best judgement when deciding on whether or not to wear chukkas to work.  A more formal work atmosphere may frown upon these.

Monk Straps – Monk straps have a single or double strap at the top instead of laces. These shoes are great for casual wear and the office but not for formal occasions.

The single strap can be more comfortable than the double strap, but the main difference usually comes down to which look you prefer.

Penny Loafers – Penny loafers are slip on shoes that can be worn casually and possibly to the office. The defining attribute on these shoes is the slit at the instep.

Plain Loafers – Plain loafers are another form of slip on shoe with no defining features whatsoever. The leather will dictate how formal this shoe is.

Side Gusset – The side gusset is a slip on shoe with elastic sides for a nice snug fit. These shoes can be worn to any occasion.

Split-Toe Oxfords – Split-toe Oxfords are a bulky shoe with stitching at the center. These are nice shoes for office wear.

Tassel Loafers – Tassel loafers are slip on loafers with dangling leather florets.  This type of suit shoe isn’t seen as often anymore, but was once very popular among suit wearers.

Wing Tips – Wing tips are men’s dress shoes with a brogue wing pattern on the toe. These shoes are great for casual wear and business wear.

I personally like these shoes and will sometimes wear them when I want to dress-up a pair of jeans.  Unfortunately, you’ll have to forgo this type of shoe in a more formal office setting or occasion.

wing tip shoes

Wing Tip Shoes

Shoe Maintenance

In case you haven’t noticed yet, owning a suit is hard work.  Suits, dress shirts, ties, and even dress shoes require a little extra care.  Men’s dress shoes often need to be shined and polished.

Shining a pair of shoes for the first time can seem arduous at best.  However, it gets easier each time and once you’ve got a good base on, shining your shoes should only take a few minutes.  Personally, I’ve come to find the whole process relaxing and sometimes even enjoyable.

Final Thoughts

One thought to keep in mind when buying a pair of men’s dress shoes is that the less ornate the shoe, the more formal it is.  This might seem counter intuitive, but it’s true.

While a nice pair of wing tips or brogues might require more work to produce than a pair of plain oxfords, it is less formal.  The reason for this is that the shoes with the least amount of styling will stand out the least.  This allows the suit, as well as the man in the suit, to stand out on his own.

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