Men’s style for Middle Aged Men

posted in: Style advice | 3

Two good men friends of mine, who are both successful Chief Executives, urged me to do this post: What the heck should middle aged men wear, off duty?

Let’s face it a suit is a marvellous thing.

It hides imperfections, makes most men look taller and slimmer, and give a sense that they are, well, buisness-like (smart and well organised). The colour palette is mainly neutral – grey or blue with a white or blue shirts, and sometimes a bit of excitement in the tie department. But increasingly tie-less. I asked the two middle aged chaps to tell me what they were concerned about:

  • Looking too young
    Young men smart casual
    Too young
  • Looking too old
  • Wanting to look fashionable, in a good way
  • Not embarrassing their children or wives
  • Dealing with a little “middle aged” spread,; good food and drink takes its toll
  • Having no idea what “smart casual” means

As you can imagine it is very difficult to say “wear this” because so much depends on a) your individual shape and b) your own preferences and style c) your colour palette.  So I will just give some principles and then suggest a few outfits that seem to work for lots of men.

Here are the principles

  • Wear the right size (too big and too small look equally terrible). Get things altered or have them made for you. Don’t wear tight clothes especially T shirts and polonecks (slim fitting is fine (so long as you are), but I don’t want to see your nipples)
  • Casual means comfortable. Here is an opportunity to wear merino or cashmere jumpers; softer cotton, silk or linen shirts; stylish T shirts and sweat shirts; denim, cotton or corduroy trousers. Wear understated luxury.
  • Colour is a good idea – grey/white/blue/black will always look good but be a bit daring even if it is only one item eg shoes, scarf, gloves
  • Texture can be good – tweed, chunky knits, but not if you are small or overweight
  • Stick with your wardrobe personality
  • Work with your body shape
  • Celebrate grey hair – get a good fashionable cut, and pay attention to excellent grooming
  • Wear casual shoes – brown leather proper shoes can be nice, smart boots, or quality trainer-type shoes – generally keep it more classic than young men wear

You can try a shirt and casual jacket with jeans or casual trousers. The first two gents have chosen toning shirt and trousers with a darker jacket. The third man has a more classic look with darker trousers toning with his jacket, and a lighter shirt.

Another look which is nice is a cashmere sweater or a classic style (fishman/sailor/arran type) with jeans, with or without a jacket.


I see there are quite a few pocket handkerchiefs in these images. My husband doesn’t like them (feeling they are unfashionable), but I think it is quite a nice way to bring in a little colour. If you use one don’t fold it like something in an Indian restaurant. Just stuff it in your pocket artfully.

3 Responses

  1. Lynn Mally

    Here’s what my husband (an academic) wears all the time: jeans and a t shirt. When it’s cold, he adds a sweater. On rare dress up occasions, he has some fancier pants (sometimes just black jeans) and a sports coat. When the sky is falling, he adds a tie. Oh, but we live in Southern California, so this is normal male attire.

  2. Stephanie

    The outfits I like the least here are on the younger men. The middle-aged men are so ruggedly bearded and handsome. Agree with all of your points here. A great summary.

  3. Sox

    The young men look like they have been forced by their mothers into clothes that make them feel silly. (And I think they look too small on the wearers, no matter how young and fit they are.)

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