Let's be clear up front: the clothes you're buying when you turn 60 aren't going to define your style for the rest of your life. That could be thirty-plus years — imagine writing an article for a man of 30 and expecting him to follow that plan until retirement!
Every man needs a great fit. By your sixties you should not only know the importance of a good tailor, you should have one — or several — of your own, experienced men with your measurements on hand and a good understanding of your preferences.
Younger men project authority with aggressive cuts and bold color contrasts. At your age, that's a losing game. Impress people with the weight of your years rather than the force of your personality — dress like the elder statesman, not the young gun.
Our culture is not always generous to its elders. It's obnoxious, but it's something that realists should plan for. Middle-aged men, the older man in his retirement needs to still dress like someone with places to go and people to see.
Comfortable, well-fitted clothes, same as on any other man. Classic styles are going to work better than fashion-forward runway experiments, of course — they look “timeless,” which is a really great word to have associated with you as you get older.
An older gentleman has the inherent dignity it takes to wear a double-breasted jacket well. Buck the business-dress standard by getting it in a color or pattern that wouldn't work in a boardroom: forest green, chocolate brown; heather gray.
It's the most respectable solution to heat and humidity: light-colored, lightweight cotton and linen. You'll still have your jacket on when everyone else is rolling up their shirtsleeves, and you'll feel just fine.
Own a couple pieces in tweed. Jackets, trousers, matched suits, overcoats — it's a gentleman's three-season leisure fabric. Older gentlemen look particularly good in relatively high-fronted jackets with plenty of pockets, usually flap pockets.
A full or three-quarter length wool overcoat is the senior gentleman's best friend. It's well worth having one custom-made to get the perfect fit in the shoulders — with a straight coat, everything else follows from that, though some men like a bit of taper at the waist or flare at the hem.
Have a classic black tie dinner suit made: tuxedo jacket with either peak or shawl lapels, plain-front trousers with the proper braiding, white formal shirt, and all the necessary accents (black bow tie, shirt studs and cufflinks, dress pumps or highly-polished black oxfords, and so on).
Waistcoats are another of those looks that seems made for the dignity of an older man. Of course, one of their initial functions was covering the paunch of men who'd let themselves slip a bit, but you don't have to be expanding at the waistline to benefit from the nappy look.
- Logo T-shirts - Novelty neckties - Hawaiian and camouflage prints.