This article was last updated on April 16, 2022
One thing I often hear from my lady friends is that their man shows them a good time, listens to them, knows how to be Mr. Lover-Lover, and is, in general, totally worth holding onto. He’s handsome, reliable — a solid guy. But there’s just this one thing that they wish he was better about: dressing.
They wish he would lose the hoodie and tight jeans and trade in those scrubby sneakers for something a little more put-together. Nothing too extreme, just a well-intentioned upgrade. It’s like he’s been cooking you spaghetti all this time, and now, you want a risotto. Feel me?
You need to educate him and present him with clear options. Steer him in the right direction with a gentle-yet-strong hand. You’ve got it! Here’s how to help your dude step his game up without making him feel like an extra trapped on the set of Designing Women.
**Note to new lovers: While my methods are sound, you definitely don’t want to begin this mission until after you have reached some milestones in your relationship (at least a few out-of-town trips, scandalous photo exchanges, etc) so tread lightly and good luck!
Menswear fashion blogs and sperm count studies have both proven that skinny jeans are not a good look for dudes over the age of 24. Your guy might not know that the trend clock for low-rise, peg-legged sausage cases ran out a few years ago, but fear not, easing him into a more flattering, straight-legged cut isn’t going to be hard. For one, just have him avoid anything marketed as “skinny” or “super slim,” unless he wants to dress like a tween. If he pushes back, just show him photos of Fall Out Boy. That always scares ’em straight.
For a first purchase, a pair of dark-blue, button-fly Levi’s 501s is the gold standard. If he is a little fancier and on the trimmer side, have him spring for a pair of A.P.C. new standards, which are cut cleanly and sharply and tend to run a little French (if you know what I mean). No matter what he decides on, he will thank you when his cash, keys, and other prized possessions all have room to breathe. Plus, sexy time is much more fun and spontaneous when it doesn’t require a pair of pliers to dispatch his offending nuthuggers.
If your dude is already rocking shirts with collars and his leisure look is more Vampire Weekend than casual Friday, you can recommend he ditch his sneaks and try on a pair of slip-on penny loafers like these Bass Weejuns. These have been making a big comeback the past few years and appeal to fellas who are exploring the always-handsome “cool grandpa,” “pothead professor,” or “preppy hot shot” styles of today. Gently explain to him that polished loafers are just as obnoxious as cement-soled Jordan reissues (in a good way), and if he is open to displaying a little Uptown edge, you would strongly approve.
And for the man for whom the loafer is a no-fly zone, gummy-soled desert boots can be his first solid step to a more grown-up shoe game. A pair of desert boots that have been sufficiently worn in say, “I’m sharp but I’m not trying to be anyone I am not.” They are chill, unassuming. They go great with everything from a sweatshirt to a tweed blazer to a polo and don’t cost more than a decent pair of gym shoes. Plus, they look even better when they are funked-up and a bit dirty so he won’t feel precious breaking his new dogs in.
The hoodie is the security blanket of the modern preswag male. Dudes h8 giving them up. To ensure a relatively painless transition, you need to hook up him with a solid, heavyweight sweater that can take the place of his favorite sweatshirt. Avoid stuff that’s too thin and dainty like Merino wool — that’s way too European for your dude. Instead, get him one of those fluffy “Shaggy Dog” sweaters that preps have been wearing since forever. J.Press are the OGs of the style, but if the price is too steep for your dude, Polo Rugby and J.Crew both make similar models in a wide range of manly colors, as well as some more “experimental” tones.
And if that is too much for him, just have him swap his hoodie for a nice, collegiate-inspired, gray, crewneck sweatshirt. He can cop one at the mall, throw an oxford shirt underneath it, and instantly look 100x better than any of the scrubs at the food court.
I really mean it when I say that most dudes don’t actually realize how gross their bathrooms are. It’s not because we are a bunch of slobs (although some of us are); it’s more that when we have work, rap, booze, and music to preoccupy our teeming minds, we don’t spend too much time thinking about gussying up our tubs or refreshing our supply of TP. Admit it, you sorta like that about us. But there’s a big difference between being a man’s man and being a barbarian. And you gotta be firm and real with your dude about that.
Let him know that if you are going to be spending the night, it would be super-duper thoughtful and cool if he would take 30 seconds to complete a few important tasks before your arrival. He should windex his sink (many guys are still sadly unaware that whatever a boner killer is called for ladies, having hair in the sink is it), wipe down his mirror, and have two clean towels ready. That’s the trinity right there.
If you are a regular guest at his place, unisex face wash, bougie toothpaste, and some sort of non-European-sounding moisturizer can all be smuggled in with minimum fuss. With any luck, he’ll read up on what you bought him, and you can spare him the anxiety of picking the stuff out on his own. And don’t freak out if you see a dope kit from Keihl’s hidden underneath the sink a few months later. He’s just exploring.
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