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Let's start with the jeans. Go for something darker that will fit his legs nicely and make sure the waist is actually his size. Many fathers I know assume that an extra inch makes them look slimmer. It does not.
Every man's style is a little different, but an oxford shirt is one classic everybody can agree on. It works with denim, chinos and suits any time of year. If your Dad is used to wearing "blousy" shirts, then start with this.
I can't stress the importance of a casual shoe that isn't a super-padded sneaker. That worked for George Banks in Father of the Bride, but he owned a shoe factory. Get pops into some casual lace-ups. Don't let him lose it at the shoes.
Now that we've covered the basics, it's time to look to accessories. I'm a huge fan of Warby Parker sunglasses—they're well priced, classic and hold up against a lot of wear.
A good timepiece is important. Chances are he already has a watch to wear, but giving him another option never hurt. If he has a metal band, go with leather and vice versa.
Undergarments, they're important. Hanro makes a super-soft pair of boxers that will last much longer than your average pair. A new pair of underwear is never a bad idea.
Rolling suitcases are not a good look. A simple duffle bag will have plenty of room for a long weekend worth of clothing. This waxed one from Jack Spade will age really nicely too—a sound investment.
You might be rolling your eyes, but a polo is one of the most versatile pieces a man can own. Dad can throw it on for the golf course, under a jacket or just bumming around. Just please, for the love of god, make sure it fits.
A clean shave never hurt anybody. Harry's mission is simple: "a great shave at a fair price." Can't argue with that.