Any asshole with a tailor can look decent in a suit, but it takes more than that to truly be a “style gawd.” Even with the abundance of knowledge that the average gent can access thanks to the glorious Internet, many of you still find yourselves in the unfortunate position of being completely and utterly swagless.  So—starting right this very second—we’re taking it upon ourselves to help redeem a few poor, pathetic bastards who sought out our steezy wisdom.

When does floral not work, and is it possible to ever wear too much?

That’s a good question. I was just gonna leave it at that, but I realized I probably wouldn’t keep this job very long if all I did was answer questions with “Good question, IOENO either.” So I’m gonna assume you’re asking if floral patterns can actually fuck up an alphet instead of adding a touch of whimsy and a “pop of color.” And I’m gonna say, very definitively: Yes and no. You should consider floral and camouflage two sides of the same patterned coin. Which means that small doses are key. If you’ve got a pocket square or a tie or a bucket hat that happens to be decked out with all-over peonies, go ahead and wear it, my guy. Just don’t mix it with a bunch of other patterns and shit. Which is my longwinded way of saying that the only time floral doesn’t really work is when you wear that shit head-to-toe. Also you’ll want to avoid a birds of paradise print because that shit is PLAYED THE FUCK OUT. — Jon Moy

What is one piece that can have me stuntin’ on the haters all year round? 

Yo, my man, I hate to be the one to break this to you, but this question is in and of itself evidence that you’ve clearly taken an “L” on this one already. Stunting on haters is a fucking mindset—a lifestyle. There is not, and never will be, that one single piece of clothing that will help you achieve this self-actualization of unstoppability. As soon as you realize this fact, you can truly start the lifelong process that is flexing on your enemies and thriving, while they perish a thousand deaths. — Lawrence Schlossman

Put an end to the uncertainty: If I’m wearing a navy suit, do I wear brown shoes or black shoes?

I’m sorry, when did we transport back to 2008? Excuse me while I boot up my LG Chocolate, log in to my Blogspot account, and check KanyeUniverseCity to see if ’Ye has posted any conceptual Japanese architecture in the past 12 hours. Do you have questions about Red Wing boots and casual bowties, too? Sorry, duder, but just FOH x a million with this basic-ass question. Having said that, black shoes. Black and navy is the end-all, be-all combination—not just for suits, but for any and all alphets you may need to put together. Jake Woolf

I’m looking for a good pair of “tailored sweatpants.” Is it worth going to Acne Studios to drop my rent on some sleek, black jawnz to pair with the thousands of white shirts I have?

Yes, you should absolutely pony up the dough for a pair of sweats that are not going to make you look like you’re on the ass end of a litigious divorce and thus are currently living with your friend Andrew until your credit score is back over 700. Our personal favorites are and will forever be from John Elliott, because they are top-tier quality and retail for the totally reasonable price of $170. Plus, he pays us to say that. More mainstream brands like Club Monaco and J.Crew also make solid options for around $70 or $80, but if you’re going to be wearing them as often as you would your favorite jeans, then why not spend the same amount of money? — J.W.

I see the appeal of bucket hats, but I don’t know where to begin. Can you recommend me a bucket hat so I don’t end up looking like RiFF RAFF? 

I’m giving you the benefit of the doubt and not moving your question directly to the trash bin for comparing bucket hats to RiFF RAFF. Bucket hats are manna from heaven…if manna from heaven was a brimmed hat instead of a miracle food that fed people in the desert. I understand your trepidation, though. A lot of dudes put on a bucket hat and they end up channeling “v. old white guy on vacation who somehow got separated from his tour group.” My thing with most guys and hats is that they’re just not used to seeing themselves in a bucket, so obviously it looks kinda weird and silly. But the thing about bucket hats is that they are weird and silly. You just gotta get used to seeing yourself with one on. My recommendation for a decent starter bucket hat would be anything in a dark, solid color. I’m thinking dark navy blue. Engineered Garments makes some great bucket hats. Keep it simple and I promise that you’ll be out there flourishing, smoking blunts, and living life like Redman, one of the bucket hat demigods. — J.M.

I hate how my iPhone looks in my pocket. It fucks up my entire look. What’s the best way to combat this problem?

First off, thank you for your question. Second off, maybe you’re just wearing your jeans too tight. I mean, if you can see the EXACT outline of your phone in your pocket, I’m more concerned about the health of your gonads, my guy. Did you know that fish have their gonads near their hearts? We evolved to have gonads that descend outside of our bodies because we are warm blooded. So don’t fuck with Mother Nature by wearing skinny jeans. But for real, if you aren’t willing to just put your phone in your back pocket or your coat, then maybe just wear slim jeans instead of skinny jeans? Actually, just get some tight-baggy pants, which are the new skinny jeans. What are tight-baggy pants? Pants that are kinda baggy and/or drop crotchy and then get tight below the knee. Which means you can still put your phone in your pocket without a struggle. Or you could just get a Skytel pager and then borrow your friend’s phone to call back that girl who is surprisingly adept at beeper code. — J.M.

Every time I think I’ve discovered something new, I get handed my late pass. How do I stay ahead of  all the trends?

For starters, you should be reading Four Pins, obviously. Bookmark that shit, check it every hour on the hour, live it, breathe it, and make it a part of you. Next, be prepared to spend all of your monies. I know, constantly dropping your hard-earned coinage on nothing but jawnz is a slippery slope, but you gotta sack the fuck up. Trends are, well, trends: fleeting moments of hot fire that need to be realized, sniped, and executed before they are merely a passing ship in the night. Staying on top of this shit is gonna take the better part of all the effort one can muster. Once you’ve mentally and physically committed both your life and checking account to this pursuit of fashionable wares, it’s time to cop everything and anything that is remotely “on and popping.” That way, there will never be a trend you haven’t at least tried. Welcome my friend, to your new life—a life that you have chosen just as much as it has chosen you. — L.S.

This feature originally appeared in the August/September issue of Complex.

Illustration by Duke Aber

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