Over-50 Shoe Solutions for the Modern Guy

Your shoes make a statement. Make sure they're telling the right story.

Men’s style over 50 is always a bit of a confusing struggle. Should it be forward looking? Should I be wearing what I did at 40 or even 30? How should things fit?

The short answer to the above questions is: Be modern, be classic, and no, you probably should not dress like a hipster. They are playing with ironic fashion; on you it will just look like you are stuck in the 1990s.

Shoes to Avoid

The first and most important part of the challenge is the footwear. The shoe leads. The shoe more than anything is making a statement. Some simple suggestions would be to start with what to avoid wearing: Converse Chucks — these can work on fashion-forward women our age, but on us they seem sad. They pronounce us to be man-children, which is fine if you are 20, but embarrassing at any age over 50. However, white low-top Converse in summer with white laces are a beachside exception.

Also to be avoided: Anything that is the “dad” look. This is a look that is, similar to the hipster, an ironic take on footwear. Worn by people like us it is just full-on dad in not such a good way, as it is being used to describe something your dad would have worn, and should be avoided.

What About Socks?

Socks are another troublesome area. Our rules are: Never wear white sneakers with black socks, never wear a white athletic sock with anything other than athletic shoes, Paul Smith socks rule, when in doubt go for something with a nubby texture.

Elevate Your Sneaker Game

This is not to say that all sneakers are out, not at all. But the sneaker game needs to be elevated. Nike Air Max 90s in a monochrome ivory can be great. Also Common Projects makes a very nice leather-topped rubber sole sneaker that will say modern, casual, but not teenager. Of course, stay far far from anything marketed as a “comfort shoe.” Yes, some people have genuine podiatry issues and they should wear what attends to those needs. For the rest of us, the “comfort shoe” may be in our future, but that time is not here yet.

Stylish Classic and Modern

The message is that you are an intelligent, discerning man who has been through decades of style changes, and you know how to navigate the intersection of stylish classic and modern. Although we know men who wear a leather-soled boot, or even classic wingtip, our suggestion is, for most occasions, stay with rubber-soled shoes. Even a classic Stan Smith can work, or the crepe-soled desert boot.

What you want is understated elegance with casual confidence. Doc Martens are out, combat boots are out, uptight leather-soled shoes, except for actual formal wear, should be carefully considered before wearing.

If in doubt, send us questions. We are happy to dialogue on our sartorial thinking.

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    • Game on. Sorry to be the one to pull the bandaid, but it had to happen. The Chucks gotta go- almost always. There are exceptions, and I would put your own personal “Steve McQueen” style as one of them. You have a relaxed easy timeless elegance that makes you the rare person who can pull off Chucks. On all but the most style savvy, and I would include Omar in this group, they look like a sad reach back to a time that is best moved forward from. As to Nike, one needs to be judicious. The super tech look doesn’t work unless one is exercising. But the older classics- AirMax 90, Gazelle, etc can work. Personally, I live in ivory/white AirMax 90s in summer, and all olive green ones in the winter. This is a bit narrow minded of me, and I need to expand my range of the semi-wide sneaker that looks good with dark jeans.

  1. I’ve been wearing Stan Smiths for decades and felt like maybe I should change so went looking and found your article. But now I think I’m okay since you mention them specifically! They are classic. I did go through a phase of not wearing socks with them back in the ’80s, but I grew out of that…

  2. David, I’m 55 and pride myself on having some fashion sense. I just purchased a pair of Toga Virilis, black leather fringed, wingtip boots with metal accents. Please look them up and tell me what ya think for a guy my age. I think they’re pretty versatile.


  3. I am 51. I was told my recently purchased white w blue trim new balance sneakers were old man shoes …
    Just bought some Stan smiths. Can I wear tall white socks with these or is that a no go?

    Thanks for the article.
    I obviously need help !

    • Yes! JFK wore white socks, and you can too. You want some that look athletic without being cheap looking. My style icon Jonathan Cheung, former Global Design Director at Levis always wears white socks and white classic sneakers, and he is one very cool guy. Make sure the pants fit well and the the break or lack there of is intentional. That is the main mistake men make.

  4. Hi,

    Wife has been saying for me to buy some trainers to wear with cargo shows etc. However I walked through JD, Sports Direct and I was at a lost. Did like the idea of Nike Air Force 1 plain white. But at 6’5″ 19st and a size 11 to 12. They looked like I could rent them out as a BnB..!!!


    Normally wear Karimor Trek trainers….. everything else is casual DMs due to health issues or Loakes. No other casual footwear.

    • Hi Heath,

      Have a look at the Nike Tailwind 79. It is slimmer and has a nice vibe. They seem to release new colors all the time, but the good ones to go specialty site like The End.


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David Stewart
David Stewart
David is the founder and face of AGEIST. He is an expert on, and a passionate champion of the emerging global over-50 lifestyle. A dynamic speaker, he is available for panels, keynotes and informational talks at david@agei.st.


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