I am now in my forties and despite having a fairly relaxed attitude to what I can and should wear, it is always possible to look like a mid-life crisis guy by wearing inappropriately youthful footwear at my stage of life.
Nobody wants to be “that” guy who is obviously trying way too hard. Sneakers can look great, but not with everything all of the time. When and where is it cool to do so then?
Sneakers are 100% cool for weekend wear. I like wearing a comfortable pair of Nike, Adidas SPZL or Saucony when I am off for the weekend. It’s almost a middle finger to the relative formality of the working week that has preceded it.
Comfort must be considered too. It’s easier to hare around a supermarket, followed by the swimming collection, in between a Scouts drop off in cushioned shoes rather than leather soled brogues! Practicality is a big plus.
A nice shoe in a white, grey or blueish hue, will sit nicely with most denims and chinos. I still find turning up the trouser leg makes the look that bit cooler. Your look (and your denims) will be totally ruined by having material hanging down the back of your sneaker.
Going for a coffee or lunch
I would wear a more fashionable sneaker out to coffee or lunch. By more fashionable, I mean a sleeker, more minimal shoe. Like these below
Team them with chinos or decent denim for a laid back cool look. Adidas Stan Smith would be the standard-bearer for this type of tennis shoe like sneaker and are a good price-point. Minimalism will always be cool in my book. Your clothes don’t have to shout, as long as YOU are happy in them.
Cinema or Theatre
You’ll be in the dark for most of these outings (literally and possibly metaphorically), but don’t let that be an excuse.
As above a cool, clean look will make you feel the part. Add a jacket or blazer to your look and you are really getting it on. You could go more casual with a bomber or leather jacket. Just make sure glow in the dark laces are not included.
Yes, sneakers/trainers/runners are totally cool and acceptable for us older guys. Not all of the time though. Like, I wouldn’t wear them out to dinner with my wife. That’s what brogues/wingtips/boots etc are for. I wouldn’t wear them if I was going to be out late either (perish the thought). They are a great option during the daytime and you will look as if you are trying, but in a good way and just enough!
Brands to look out for-
Common Projects (ultra-cool if you can afford it)
Adidas Stan Smith (the classic must-have)
Nike Cortez (range is pretty cool and well-priced)
Nike Flyknit (all over the local gym. Hipster faves)
Fred Perry (Kendrick leather versions)
AMI Paris (see my ones above. Lovely quality)
Gucci (unless the mortgage is due)
TIP– If you are looking to spend a bit on new ones, the sales are just around the corner, so hold fire for a couple of weeks!
Thanks for reading. Hope some of the above was helpful.