I need a new menswear icon for Fall.

Look no further than Joe Pera.

What about some icons that are less … 

“Staid?” Sure thing. Research David Hockney in the 70s. Or, better yet, look at what Tyler, the Creator’s wearing. Tyler, the Creator is the best-dressed man on the planet right now.

Sarah writes: I love a man in dark denim and a tee, but the man I love is a business casual kind of dude. His go-to outfit is a long sleeve button down paired with navy chinos and loafers. Is there a way to introduce some edge into his closet without cramping his style?

Like any really good question, this one has several answers. Let’s start with the easy one:

No single article of clothing is more versatile and at the same time more capable of instantly adding a little grit to a wardrobe than a denim trucker jacket. A denim trucker jacket is light enough for your man to wear in the fall. It’s a perfect layer to take deeper into the colder months. He can wear it with anything. Pair it with chinos and he’s already somewhere between Judd Nelson in The Breakfast Club and Martin Sheen in The California Kid.

You’ll love it. He’ll probably be okay with it. But that’s the real question, isn’t it? How edgy can it really be if you picked it out for him? Because either he feels most comfortable in a “business casual” mode of outwardly expressing his appearance — and people do feel this way, strange as it may seem — or he feels uncomfortable dressing in other ways. In the former case, you just have to accept that this dude isn’t super concerned with clothes, and if he’s otherwise presentable, that ought to be okay. But in the latter case, there is opportunity.

Your average guy, even in 2018, has one goal when he gets dressed every morning: to not look like an idiot. That feeling, that hesitation — that fear that results in a weird sameness, which is why, once you notice that one salmon-and-grey checked shirt, you’ll see it everywhere.

In order to make the jump from merely looking acceptable to really dressing well, you have to start standing out, so you have to risk looking like an idiot. And that’s not always an easy thing to make a case for.

Luckily, there’s another technique, but, to be fair, it may be too advanced for your man. The idea is to take preppy, business casual signifiers, and imbue them with your own subversive sense of private rebellion. Miles Davis pioneered this technique in the late 1950s. Thom Browne has made a career of it. André 3000 mastered the approach in the late aughts. Around that same time, STAG sold a Jack Spade tie with little pills and sunglasses on it that was just perfect.  Part of the trick is that the quality and craftsmanship of what you’re wearing has to be greater than or equal to the “real thing.” Because done right, the people around you won’t recognize the subterfuge right away. It’s the best. And he’ll feel less like an anonymous drone and more like an undercover agent.

Bo Fahs is a writer in Austin, Texas

Illustration by Nick Francis DiFonzo

Submit your questions to askedandanswered@stagprovisions.com