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In advanced middle age, sartorial quality is the dapper dad's best friend. Here, a chic yet casual blazer gets added lift from a pocket square. Zara blazer, $99.95 through Pocket square, $30 at Got Style (

Fred Lum

Question: Dear Mr. Smith: I'm afraid of Father's Day. I don't like being reminded that I'm a dad, because it makes me unsure of what I can wear. I'm 55, not yet a granddad, but past hipster. How fashionably can I dress without looking as if I'm trying too hard? For example, if I wear the same style of fedora as my daughter's boyfriend, will I look silly? And how about shirt-tucking?

This one troubles us all. A couple of years ago, I was taken with a black wool sweater with a giant white skull and crossbones woven into it. When I brought it home, my partner said it made me look like a director of rock music videos. Ouch.

In other words, I was just too old, trying to look like one of the kids in the way of your most embarrassingly earnest high-school teachers. It's a bit like trying to keep up with the slang: No matter how much you say "sick" and "hype" and "bro," no matter how much you fist-bump, you are going to get it wrong somehow.

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That said, there's no need to disappear into beige trousers and cardigans once you hit 40 or become a father. You don't need to abandon all aesthetic flare. In advanced middle age, sartorial quality is your friend.

You can go flashy if it's good flashy - and by flashy I mean Etro, Varvatos or Prada, not Stussy and Quiksilver. The baggy pants and T-shirts that are so flattering on teenage skateboarders look frumpy on a guy with a belly. And the red plaid lumber jackets or team bombers that look ironic on 19-year-old guitarists with beards make those over 40 simply look unemployed.

Hats, as you mention, are particularly tricky. Fedoras just make you look older: They are a sign of fussiness. It's as if they all come with mustaches. Ball caps are a sure sign you're bald. Generally, I would avoid hats except as practical protection against cold or sun. (And if you must, try a porkpie over a fedora.)

As to tucking, you're in luck: Current fashion favours hiding your shirttails. Even young guys are doing it. So you can dress like a grownup without fear of appearing square. (I don't believe, either, that hanging an untucked shirt over a bit of a paunch has exactly the camouflaging effect that most guys think it does.)

So what's cool dad fashion? We styled a few outfits for out-of-the-office wear that won't make you look either old or desperate. A forward suit worn without a tie says effortless polish. A work-wear-inspired look conveys easygoing chic. And the classic pocket-square-instead-of-a-tie is well suited for a weekend night out. (Warning: It's becoming something of a uniform among the 40ish urban set.)

Finally, remember that good-quality yet sober shoes - not cool sneakers - are a subtle way of expressing style while remaining dignified.

Ask Mr. Smith a question, or view the complete archive, at Russell Smith's online advisory service,

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Wardrobe Dont's


  • They may be needed in the sun, but we see them as a necessary evil. They usually look fussy. Ball caps are for children or the nervously bald. And no hats indoors!


  • Slimmer fits, please. We're big on gingham right now. T-shirts must be new - i.e. not faded - and not bear advertising. A wider boat neck is elegant. Polos with logos from corporate golf events are pretty much the most middle-aged thing a man can wear.


  • No turtlenecks, patterns or grandpa cardigans (despite what you see on young fashion designers).


  • Never wear a logo tie, joke tie or very wide tie. When in doubt, ask your significant other.


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  • A plain, dark-coloured one is fine. That huge D&G logo is not.


  • Narrow khakis can be sublime with a linen shirt, but with a golf shirt you'll look like a fundraiser for a provincial Conservative party. For denim, always go dark.


  • Deck shoes are for the insanely conservative. You can actually pull off showoffy sneakers like Vans or Airwalks if you're confident. Failing that, classic workwear boots like Redwings or Blundstones are always hip.

Fanny packs

  • Never under any circumstances.
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