Theory: there are fashionable dudes and then there are fashionable DADS, and the two are very different creatures. Regular old fashionable dudes (unmarried, childless) don't have a full-blown existential crisis when they put on a fedora. They're perfectly happy wearing tight jeans and peacocking at the bar with a well-stirred Manhattan in one hand and a carefully worn-in book of Nietzsche in the other, and they don't think it's weird to spend money on themselves (AKA more than $10 on a pair of jeans).
But fashionable dads are a different story.
Everything's just so much more complicated when you're a fashionable dad. A simple act of fedora-wearing suddenly means you're "trying to hard to imitate your teenage son." Tight jeans are now "inappropriate," spending a lot of money on a nice pair of leather shoes is "irresponsible" (think of your fedora-wearing son's college fund! Think of all the fedoras he'll need in grad school!). And so the dad with a secretly fashionable soul never buys anything nice for himself. He's petrified that he'll look like he's clinging to his lost youth — when really, he just enjoys a nice cufflink and a quality spritz of cologne every now and then. Is that so bad?!
Whether your own particular papa has dreams of moving to Brooklyn or just spends a lot of time keeping his beard well-coiffed, Father's Day is the time to say, "I see you, Dad, and I appreciate what you've got going on."
Why: You've caught him staring longingly at the Wikipedia page for Silicon Valley, wondering why he didn't invent "the Twitter." He may not be planning his app's IPO anytime soon, but with a leather messenger bag, he'll look like he could.
Why: There's lounging and then there's Instagram-worthy lounging, and these sorbet-colored pants demand the latter. Burn Dad's ratty old long-johns and let him know you'll be expecting to see some "from where I stand" photos on social media at least once a week.
Why: Aw, he knew this day was coming. Dad's been shaving with the same janky razor since he was a young buck, so it's definitely time for an upgrade. I'm talking a shaving brush made with pure badger hair, a razor-and-brush stand, and a monogrammed apothecary mug for whipping up a nice old-fashioned lather. Make sure you clarify that this doesn't mean you're okay with a handlebar mustache.
Why: Who knows what cheap, alcohol-drenched aftershave Dad's been patting on his cheeks, but it's time for a scent that's almost as good as a vacation.
Why: He's always been a little bit iffy on jewelry, but that's because he didn't know it could look this manly. The tiny Buddha head will remind him to stop stressing about that retirement fund, and the gorgeous detailing will make him the hippest attendee at the block party by far.
Warbly Parker Dean Sunglasses, $95, Warbly Parker
Why: Because all the cool kids are wearing them, and who was the OG cool kid back in the '70s? Dad, that's who.
Why: To celebrate their 75th anniversary, Blue Note has been remastering the jewels of their catalog in hi-def resolutions. The result is classic, vintage cool with a quality upgrade — just like Dad, now that he's started his half-marathon training.
Why: It's simple, classic, and just a tad kitschy. Plus, he's always been a bit of an Anglophile.
Why: Dad would never buy himself a $200 robe — in fact, you should probably keep the price tag to yourself. But you're always trying to get him to lounge more, and now he has no excuse. Plus, he'll look great when he goes out to get the mail (because if anyone still gets mail, it's Dad).