We’re staring down the barrel of 2025, and some of you are still clinging to fashion choices that should’ve been retired with dial-up internet. I get it, comfort is king, and some trends just felt right. But trust me, what felt “right” ten or even twenty years ago might be screaming “fashion emergency” now.
It’s time for a reality check, a closet cleanse, and a no-nonsense look at what needs to go. If any of these hit home, don’t get defensive. Just open that closet door and get ready to upgrade your game.
Head-to-Toe Gorpcore Overload
Look, I appreciate a good hiking trail as much as the next guy, but unless you’re actually scaling Everest, why are you dressed like you’re about to? Gorpcore—that head-to-toe outdoor gear look—had its moment. By 2025, rocking a puffy trail jacket, a utility vest, and cargo pants all at once just looks like you’re trying way too hard. It’s overkill, and frankly, it screams “I got lost on the way to REI.”
Instead, pull it back a notch. One functional outdoor piece at a time is the way to go. A quality fleece or some trail
Y2K Fashion Throwbacks (Overkill)
Nostalgia is cool and all, but some Y2K fashion should stay firmly in the early 2000s. We’re talking big baggy cargo pants, trucker hats with giant logos, and those rimless wraparound shades that made everyone look like a low-budget action hero. A touch of the past is fine, but going all-in makes you look less retro and more like you’re trapped in 2003.
Your kids shouldn’t confuse you for a throwback photo of yourself. Moderate the nostalgia, fellas. Pick one vintage-inspired item—maybe a cool band tee or a classic denim jacket—and let the rest of those cringe-worthy trends from the early aughts fade into obscurity. Some things just haven’t aged well, like JNCO jeans or flame shirts.
Perched “Gnome” Beanies
What is it with those tiny beanies that just sit on top of your head, barely covering anything? You know, the ones that look like they’re about to fall off, offering zero warmth or actual style? They’ve been around, but by now, they’re more of a punchline than a fashion statement. Unless you’re auditioning for a garden gnome role, it’s best to ditch the mini-beanie.
A beanie’s job is to cover your head and ears. Opt for a classic beanie style that actually fits. It’s a timeless, masculine look that serves its purpose. Don’t be that guy whose hat looks like it’s trying to escape.
Baggy Jorts (Jean Shorts)
Let’s be blunt: baggy jean shorts, especially those knee-length or longer monstrosities, are the worst legwear known to man. They scream “stuck in the ’90s” and make you look sloppy. If you’ve got a pair of these denim disasters lurking in your closet from yesteryear, it’s time for an intervention. Denim was never meant to stop at the calf – let’s keep it as pants or not at all.
For summer, ditch the baggy jorts. Instead, go for chino shorts or more tailored shorts that hit above the knee. They’re cleaner, more flattering, and will instantly update your summer style. Trust me, your legs (and everyone else) will thank you.
The Mullet Revival
Okay, I know, I know. The mullet – business in front, party in the back – has had a bizarre resurgence with the younger crowd. But for the average 35–55-year-old man, trying to rock a mullet in 2025 is more likely to draw confused stares and giggles than compliments. Unless you’re starring in an ‘80s cover band, it’s time to let the mullet rest in peace.
Some trends were left behind for good reason. This hairstyle, while “ironic” for some, just looks ridiculously outdated on a grown man. Choose a modern haircut that actually suits your face and your lifestyle. You’ll thank me later when you’re not getting mistaken for a character from a B-grade action movie.
Sporty Wraparound Sunglasses
Remember those curved, sporty shades, often mirrored or with colored lenses, that were all the rage in the late ’90s and early 2000s? Yeah, those. Unless you’re a professional cyclist or a highway patrolman, those wraparound shades aren’t doing your look any favors. They instantly remind people of dated athletic wear, not modern style.
Upgrade your eyewear, my man. Classic frames like aviators, wayfarers, or even some sleek clubmasters are timeless for a reason. They exude sophistication and confidence. Ditch the high-tech, plastic-y look for something that says “I know what I’m doing,” not “I just finished a triathlon.”
Ultra Skinny “Spray-On” Jeans
The super-tight, spray-on skinny jeans trend had a good run in the 2010s, but that pendulum has swung. By 2025, anything that looks like it was painted on is out. These jeans are often unflattering, emphasizing areas you might not want to highlight, and for men over 35, they can make you look like you’re trying too hard to cling to your youth.
Give your legs (and your circulation) a breather. It’s time to retire those spray-on skinnies. Transition to slim-straight or athletic-fit jeans. They’re more comfortable, universally flattering, and give you a more balanced silhouette. You’ve had your fun, now let’s move on to something that actually looks good and feels good.
Excessively Baggy Pants
On the other end of the spectrum, we have the excessively baggy pants. I’m talking about jeans or trousers that are three sizes too big, pooling around your ankles, and swallowing your shoes. While a relaxed fit is perfectly fine and even stylish now, drowning in fabric just looks sloppy and makes you look shorter. If your pant legs could double as a sail, they’re too baggy.
There’s a clear difference between comfortable and chaotic. Get rid of anything that completely distorts your silhouette. Aim for a straight or slightly tapered leg opening that breaks properly at the shoe. A well-fitted pair of pants, even if they’re relaxed, always looks more put-together and confident.
Super Tight Suits (Spray-On Suits)
Remember when suits were so tight you felt like the Incredible Hulk about to burst out of them? That ultra-slim tailoring had its moment, but by 2025, it just looks uncomfortable and outdated. A suit should skim your body, not squeeze it. For men in their 40s or 50s, a too-tight suit doesn’t make you look younger or fitter; it highlights every wrinkle and restriction.
It’s time to retire those old spray-on suits or get them altered. Proper fit, which leans towards comfort and a slightly looser drape now, actually looks more sophisticated and modern. Invest in a suit that fits well in the shoulders and drapes cleanly. You want to look sharp, not like you’re shrink-wrapped.
“Broccoli” Haircuts
The “broccoli haircut”—where the sides and back are shaved short and the top is left long, curly, or permed, resembling, well, a broccoli floret—is another one of those fleeting trends. It might be popular with the Gen Z crowd, but for a man in the 35–55 range, trying this youthful, experimental cut can scream “midlife crisis” or just look wildly mismatched.
Some hairstyles are just of the moment and won’t age well. While it might be called broccoli, it’s not doing your image any favors. Opt for a more classic, flattering hairstyle that works with your hair texture without the extreme contrast. Don’t fall for overly trendy cuts that will make you cringe when you look back at photos.
Socks with Sandals (or Slides)
Alright, gentlemen, this one’s a classic style sin, even if some comfort-loving dads and ironic streetwear enthusiasts tried to make it a thing. Wearing socks with sandals or slide-on slippers in public just looks lazy and clueless. Yes, we know it’s comfy, and yes, even celebrities did it ironically, but it’s time to stop pretending this is okay outside the house.
Socks defeat the entire purpose of airy sandals. If it’s warm enough for sandals, go barefoot in them. Otherwise, opt for casual
Square-Toed Dress Shoes
Nothing screams “1990s” like chunky, wide, square-toed dress shoes. These were trendy when Friends was still on the air, but by 2025, they are considered one of the biggest style no-nos in footwear. They make your foot look clunky and instantly date an otherwise sharp outfit. If you’ve got a pair of these lurking in your closet from twenty years ago, it’s time to let them go.
Upgrade your footwear, buddy. Swap them out for shoes with a more modern silhouette—think classic round-toe or slightly tapered (almond-toe) oxfords, brogues, or loafers. This one detail can significantly improve your overall look. Your feet will thank you for choosing a shape that doesn’t resemble Frankenstein’s loafers.
Giant Logo Apparel
Wearing clothing with oversized brand logos or graphics plastered all over it – like a huge Polo Ralph Lauren pony or massive designer names across your chest – makes you look like a walking advertisement. While logos were once a status symbol, now they often come across as tacky, especially for a grown man. Subtle style speaks louder than a billboard on your chest.
Phase out those “logo billboard” pieces from your wardrobe. Clothing with subtle or no logos looks more mature and versatile. If you like branded items, opt for those with smaller, discreet logos. You’ll look less like an unpaid sponsor and more like a well-dressed man who doesn’t need to shout about what he’s wearing.
Ed Hardy Era Graphic Tees and Accessories
If your T-shirt still features bedazzled dragons, flames, tribal designs, or rhinestones, and it reminds you of 2007, it’s time for an intervention. The loud, over-the-top graphic tees and accessories from the Ed Hardy era were a fleeting fad, and now they instantly give off an “outdated mid-life crisis” vibe. Your T-shirt shouldn’t blind people with rhinestones or make them wonder if you’re heading to a 2005 nightclub.
These pieces draw the wrong kind of attention and make you look immature. Replace them with solid, well-fitted shirts or at least more modern, minimal patterns. Let go of the blingy tees, caps, or belts with outdated graphics. Bedazzled dragons on your shirt aren’t the power move you think they are, champ.
Ask Me Anything