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How to Choose Your Next Dress Shoes

With so many shoes to choose from, it may become difficult to choose your next dress shoes. Every year we see new variations on the many designs that have persisted throughout the years. Double monk straps are becoming very popular, but for how long? We also see the same traditional colors along new colors like burgundy or even green. So, which shoes should you buy next?

Do You Have the Basics Down

You need to start off with the foundational shoes first. See, most men have 4 levels of formality in their life:


1.CASUAL: jeans and a T-shirt; going to the grocery store or to a friends house.

2.SMART CASUAL: nice jeans or khakis with a casual dress shirt; going to a BBQ or hanging out with friends.

3.BUSINESS CASUAL: chinos and a dress shirt; on a fancy date or to work.

Handmade-HandCrafted-Men-Leather-Shoes-Black Derby, aniline full grain, goodyear welt, blake stitch, formal shoes


4.BUSINESS FORMAL: suit; wedding.


You need black oxfords for level 4. Black derbies will do as well.

Level 3 gives you more options. Just make sure the shoes are not an exotic color. Many can work here: derbies, Chelsea boots, monk straps, oxfords, etc. Just stay away from more casual shoes like loafers and chukka boots.

For level 2, you have all the colors open to you. Stick to casual shoes like loafers, chukka boots, most boots to be honest, etc.

Dress shoes for level 1 would look silly.

Are you on a budget? Some brown or burgundy oxfords will cover level 4 and 3.  Some Chelsea boots will cover level 2 and 3. You want at least two pairs of whatever shoes can fit into level 3 so you can alternate.

Do you already have the basics down? If so, things get complicated at this point. You need to examine your goals.

How old are you?

If you’re younger, you can afford to experiment more. Try bold colors and designs. Burgundy is ‘in’ right now as are double monk straps. Of course, if you’re looking for more respect or maturity then go with classics. A black derby shoe is classic but still cool. As an older man, you no longer have to try to stand out. Your character is enough. That being said, nothing is more exotic than an older man with a bold piece in his outfit. Try some boots!

Where do you work? What is your friend circle like?

Look at what others are wearing. If no one has dress shoes, then some very casual dress shoes will set you apart while not making you look awkward. Try some oxford boots. If you work somewhere where people wear dress shoes, sometimes wearing burgundy shoe will do the trick. Some burgundy oxfords are formal enough to fit in.

Do you have any future commitments?

If you have a promotion coming up or a wedding, pay attention to what the required attire is.


No matter, enjoy your next purchase!


For more information about 2019 trends:

Best Dress Shoes for 2019

1 Reply on How to Choose Your Next Dress Shoes

  • It’s good to know that you can experiment more if you’re younger. My younger brother was telling me last night about how he is needing to find some dress shoes to get for the new job that he will be working at in a couple of weeks, and he wants to make sure that he finds the right shoes. I’ll make sure to pass this information along to him as he searches for dress shoes to get!

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