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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