The Gentleman’s Guide To Fashion: A Roadmap To Avoiding Blunders

By Farah J March 20, 2024

Let’s face it, fellas, sometimes our fashion sense gets stuck in a time warp with our high school AIM screen names. (RIP, Xx_dankmememachine69_Xx). But fear not! This humurous intervention and helpful guide to ditching those fashion “yikes” will stop you from doing style sins that would make even a fashion-blind grandma wince.

We’ve all been there: the questionable graphic tees or the socks that mysteriously migrated from the laundry basket to our sandals. From questionable sock choices to clothing crimes that should be tried at The Hague, we’re about to level up your wardrobe game so you can finally stop looking like you raided your dad’s closet in 1998.

If you’re ready to ditch the “mistaken identity” compliments – like being mistaken for a lost contestant on 90s Nickelodeon – then buckle up, buttercup; it’s time to say goodbye to fashion blunders and hello to looking fly!

Holey socks

Okay, why do we often see guys walking around with holey socks like it’s the latest trend? The truth is that holes in socks are a big no-no in the fashion world. They’re like tiny black holes sucking up all your style points! 

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Be brave, men, say your goodbyes and toss that sock into the trash. It’s time for some sock-shopping therapy. It’s all about finding the right fit for your feet. So, do yourself a favor and bid farewell to those hole-ridden socks! 

Slick and greasy

Boys may not like to admit it, but they secretly adore the hair care goodies. Who doesn’t love the idea of a perfectly styled mane? But here’s the kicker: it’s easy to go overboard with these products, and trust us, it’s not a good look.

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So, gentlemen, let’s make a pact to avoid this fashion disaster. You don’t want to be the guy with hair so stiff it could poke someone’s eye out. Embrace the art of moderation and keep your hair game on point without drowning it in product.

Say no to denim shorts

Alright, gents, gather around for a little fashion heart-to-heart. It’s time we talk about denim shorts causing quite a stir. Yes, those knee-huggers that are present in every man’s wardrobe. Aren’t they like that one friend who’s always around, but you’re not quite sure why? You’re always hesitant to ditch them.

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Remember, fashion is about making statements, and your choice of shorts should be no exception. Swap out those denim duds for something more refined, like chino shorts. They are way cooler and look sophisticated. Trust us, your wardrobe will thank you.

The fanny pack era is gone

Why do some men think that the dreaded fanny packs are making a comeback? Seriously, if you catch sight of someone sporting one of these eyesores, it’s like an assault on your retinas. And let’s be real, fanny packs never really made sense in the first place.

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You all need to keep it chill, dearest men, and collectively agree to leave the fanny packs where they belong, buried deep in the archives of regrettable fashion choices. Don’t worry; there are plenty of other ways to carry your keys and wallet without sacrificing your dignity. 

Cheap sunglasses

Dude, let’s talk shades! We’ve all been there, rocking the sporty shades, thinking we look effortlessly cool, but the truth bomb is, they haven’t been cool since, like, the year 2000! Those bargain bin shades with plastic frames are not doing you any favors. 

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Here’s the secret: sometimes, less is more. Skip the shades and focus on accessories like a dope hat or statement watch because cheap sunglasses aren’t adding much value to your look anyway. So throw those weird shades away and prioritize quality over quantity. 

Rainbow costume party

Have you ever noticed that some men unintentionally end up looking like they walked right off the set of a costume party? While expressing your style is essential, there’s a fine line between being fashion-forward and looking like you’re wearing a costume. 

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Remember, folks, you want to look put together and confident, not like you’re playing dress-up. Try to balance trendy elements and traditional pieces to create a cohesive outfit that reflects your style without looking like a caricature. You’re a real person, not a cartoon character.

Sports jerseys need to come off

The sports jersey syndrome is a fashion fumble that is as common as mismatched socks. Listen up, gents, sports jerseys are perfect for cheering on your team, whether you’re at the stadium or home. But once the final whistle blows, it’s time to hang up that jersey.

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Imagine wearing your lucky team jersey to a job interview or a first date. You won’t get that job and you won’t score a second date. They’re comfy, but trust us, your significant other won’t be impressed. So, men, you should save the touchdowns for the field. 


Let’s talk about clutter! How can women rock a whole arm party with bangles, rings, and earrings? The ladies look stylish but it doesn’t always translate well for the men. Pile on too much jewelry, and you go from “smooth operator” to “five-year-old’s dress-up box.”

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Guys can rock jewelry, but it’s all about keeping it sleek and simple. Think of one or two statement pieces, not a full-on orchestra on your fingers. Ditch the giant, gaudy rings and chunky bracelets because less is more when it comes to men’s accessories. 

Once upon a fur

All right, guys, wearing fur is as outdated as a flip phone. Leave the fur at home unless you’re planning a winter expedition to the Arctic. Sure, it might keep you warm when camping in sub-zero temperatures, but please don’t wear it anywhere else.

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Honestly, who wears fur in public these days? And you know what? Putting on a fur coat will leave you open to many raised eyebrows and confused, angry looks from passersby. You’re more likely to get mistaken for a time traveler than a trendsetter!

Feet insecurity?

Listen up, fellas! Some folks might try to tell you that wearing socks with sandals is comfy or even practical. But let’s be honest, comfort does not always equal fashion. And in this case, brothers, it’s a major fashion mistake, and honestly, it looks gross! 

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Sandals are designed to let your feet breathe, and socks are about keeping your toes toasty. Mixing them is like inviting your winter coat to a pool party. And obviously, it doesn’t make any sense. So next time you’re wearing sandals, leave your socks at home. 

A walking ad

We get it, gentlemen; something about rocking a logo makes you feel like you’re on top of the world. But those brand names don’t make you who you are. You’re more than just a walking billboard for some fancy label, and what you wear doesn’t define your value.

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There’s nothing cooler than being confident in your skin, regardless of the brand of shirt you’re wearing. So, next time you’re tempted to splurge on that overpriced logo tee, remember that true style is not about showcasing some fancy brand.

Dirty and beaten-up kicks

Fellas, you know that feeling of putting together a killer outfit and feeling sharp from head to toe? Then you glance down, and BAM! Scruffy sneakers with questionable stains. Not a good look. A beat-up pair of shoes can drag down even the most expensive outfit.

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We know that shoes don’t have to be fancy or expensive. A classic pair of sneakers or boots can be the perfect finishing touch, but they gotta be clean. You wouldn’t want to walk around with shoes that look like they’ve been through a war zone.

Monochrome madness

Men, unless you’re auditioning for a role in The Matrix sequel, decking yourself out head to toe in the same color is a bit villainous, don’t you think? Blending in might be cool if you’re trying to sneak past the fashion police. 

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Why don’t you all break free from the grayscale monotony and inject some life into those threads? Whether it’s a vibrant tie or a subtle contrast with a patterned shirt, it’s time to ditch the one-tone wonder and embrace the spectrum! 

Either this or that

With tie clips and vests, this look seems like someone got a little too excited with the accessory drawer. We know that vest is your tie’s best friend, but why would you add a tie clip to the party? It’s unnecessary and a bit confusing! Thre’s just too much going on.

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The vest is like a built-in tie clip. It holds everything in place and keeps your tie from flapping around (unless you’re attending a strange, themed party)! A tie clip is just a bit much! So next time you’re rocking this look, ditch the clips. You’re better off without them.

Suspend either one

This dreaded combination of suspenders with a belt has been haunting the wardrobes of unsuspecting men for far too long, and it’s time we put a stop to it. Why would anyone do this disaster to themselves? It’s like wearing a raincoat and carrying an umbrella simultaneously—totally unnecessary. 

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If the whole point of a belt is to keep your pants from taking an unscheduled trip south, why would guys throw suspenders into the mix? Are we trying to double down on pants security here or something else? We’re still waiting for an answer.

Floppy collar

Guys, let’s talk about your floppy-collar city. A limp collar is like the fashion equivalent of a deflated pool toy – all the potential for fun, but just kinda sad. But hold on, there’s a superhero in this fight, which is the collar stay.  

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These little lifesavers (well, shirt-savers) are like tiny invisible braces for your collar points. A fashion superpower with zero commitment? Yes! Now you can transform your look from “dudester” to “sharp dresser” just by sliding in that collar stay. Amazing, right? 

Check your tie length

Ah! The never-ending case of the too-long or too-short ties. Honestly, men, do you think finding the correct length for a tie isn’t rocket science? Yes, it is! Apparently, it’s something the male species struggles with—the world world of men’s fashion is wild.

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If the tie is grazing your belly button or barely skimming your chest hair, Houston, we have a problem. Note that it needs to hit right around your belt level. And don’t forget about the width, it’s just as important. You know it’s all about the proportion.

Button, button

We’re sure you know those little guys called “buttons” can make or break your look. There seems to be some confusion out there about how many to button up, and let’s be honest, an unbuttoned disaster can be an absolute confidence crusher.

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For two-button suits, button the top one. Three-button jackets? Here’s where it gets fun, “sometimes, always, never” is the golden rule. Button the top (sometimes), always button the middle one, and never button the bottom one. Find the balance. Easy peasy! Remember, buttons are your friends. 

Sneakers with suit pants

Brothers, are you trying to blend a smoothie with a lawnmower here? Don’t get us wrong, we’re all for pushing fashion boundaries, but sneakers and suit pants? This look is like mixing peanut butter with pickles. It just doesn’t quite work out.

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We get it: sneakers are versatile and comfortable, but pairing them with your suave suit? Nah! Some people might dig this look, but most of us are scratching our heads. And don’t even get us started about those high-top sneakers with a three-piece suit. Damn! 

The choice of socks matters!

Believe it or not guys, socks can be the ultimate silent assassins of your outfit! They are like the secret handshake of style. The right ones show you’re in the know, while the wrong ones? Well, let’s say they raise some eyebrows and irritate people.

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Ditch the white socks (unless you’re rocking athletic wear), and those cartoon character pairs can stay in your childhood days. And for the love of all things stylish, please match your socks to your outfit. Trust us; it makes a world of difference. 

Consider the length of the pants

Wearing pants of the wrong length is as glaring as wearing sunglasses indoors. If you think the length of your pants doesn’t matter, you need to sit down and reevaluate some things. The length is crucial whether you’re rocking jeans, chinos, or slacks. 

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Believe us; nobody wants to see pants dragging on the floor like they’re auditioning for a role in a mop commercial or hovering awkwardly above your ankles like floodgates waiting to burst. Don’t be that guy stuck in a perpetual game of fashion limbo. You’re better than that.  

The right arm-length

Sigh! The wrong arm-length debacle has become a national epidemic and needs to be addressed immediately. Some men seem to be trying to bring back the medieval look with sleeves that could double as wizard robes. Unless you’re Merlin, that ain’t a good vibe. Also, we’re aiming for suave, not sorcerer.

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It might be a little challenging, but it’s not rocket science. Just a little snip here, a stitch there, and you’re golden. Your sleeves should be like Goldilocks’s porridge—not too long or short, but just right. Let’s keep those wrists visible, shall we? It’s called fashion, look it up! 

Ill-fitting suits

Gentlemen, you know that feeling of dropping some cash on a suit for a big event, feeling like James Bond ready to take on the world? But then, reality hits! The sleeves hang like drapes, and the shoulders look like you borrowed the suit from your grandpa. A complete disaster!

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A baggy suit is the fashion equivalent of a deflated pool float. All that potential for looking sharp but ends up sad and misshapen. Here’s the thing: an expensive suit is like a sports car – it only looks good if it fits right. Think about that.

Opposite of pointy shoes

Dude, ditch the clown shoes already! Take this as a reference: Square-toed shoes are about as fashionable as a flip phone in the age of smartphones. They cut off your feet like a poorly framed photo, making them look stubby and stuck in the 90s. 

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Trust us, the ladies (and everyone else) are not feeling that vibe. Step into some sleek, regular kicks instead. Your feet (and your dating life) will thank you. Give your toes some breathing room (and the world a break), please!

Tucked-in oldies 

Tucked-in shirts? It’s more like tucked-in dreams of being a ’90s accountant, dude. Unless you’re giving a presentation on “How to Use a Fax Machine,” let that big belly breathe. Why is your shirt permanently attached to your pants anyway?

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Newsflash, fellas: the tucked-in look isn’t doing you any favors unless you want to brag about still living with your mom. Let that shirt loose and show the world you’re comfortable in your skin. Think “effortlessly stylish,” not “stuffy accountant.” 

Male midriffs

Let’s talk about the midriffs, fellas. You know we’re talking about that hairy belly peeking out from a too-short crop top or a half-cut hoodie. Here’s the thing: it’s an all-or-nothing game. Rock a full shirt or go shirtless with confidence. Being stuck halfway is not a good look.

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Showing off your abs is great…at the gym. But on the street? Unleashing your navel to the world like a cheap surprise birthday gift? Not so much. Think of your midriff as a delicious dessert: best enjoyed in private, not the main course. You have to leave something to the imagination.

Dirty white sneakers

White sneakers: the ultimate symbol of fresh kicks…until they turn into a walking crime scene, that’s what! Dudes, we get it; you like the clean look. But here’s the thing: dirty laces screaming “I’m a lazy baby” on your white sneakers ain’t fooling anyone. 

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Here’s the deal: either commit to buying white laces every wash or embrace the slightly less fresh (colored) sneakers and skip the white altogether. Or buy white laces in bulk because those bad boys will need replacing faster than your phone battery.

Suit up or suit down?

Suit up? It’s more like backpack down. Backpacks and suits are about as compatible as oil and water or maybe ketchup and ice cream. Talk about a fashion meltdown. Imagine the wrinkles and the discomfort. It’s an ugly disaster that doesn’t work. There’s no way to defend the combination.

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Unless you’re infiltrating a school for a top-secret mission (and even then, maybe rethink it), ditch the backpack and grab a briefcase or messenger bag. Anything is better than looking like you’re on your way to hike Mount Doom. Use your hands, not shoulders.

“Ugh” boots

Uggs on dudes? It’s more like “ugh” boots. Are we right or what? Listen, we all love cozy feet, but those fluffy slippers shouldn’t see the light of day (unless it’s, you know, actually night…and you’re inside). They’re the comfy slippers of champions but only when at home. 

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Stepping out in Uggs is like wearing your pajamas to a job interview—the same vibe. Stick to sleek boots or sneakers for the streets – there’s a whole world of those waiting in men’s size – and leave the Uggs for post-shower Netflix binges.

Lose the earrings

Men with earrings like pirate treasure chests resemble a fashion felony from the 80s. We get it; you’re a rebel, a total rockstar…of your basement band in 1987. Unless you’re auditioning for a Motley Crue reunion tour, lose the funky earrings. Gentlemen don’t wear them.

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Besides, the only thing those earrings should be holding up are questions like, “Uh, what year is it?” Simple studs or hoops are your friends at best. Keep it sleek and modern, and most importantly, keep people from asking if your mom still picks out your clothes.

Tiptoe crime 

Toe shoes? It’s more like a crime against Happy Feet. Seriously, men, who decided your toes needed their apartments? Do they need that much personal space? They make your kicks (well, you, actually) look like a short, rugged hobbit’s, if anything. And we’re already trying to be friendly with that statement.

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We get it, freedom for your little piggies, but trust us, they’re happier chilling together in regular shoes. These things offer about as much practicality as a chocolate teapot. Just ditch these foot freaks. These don’t make you look “different,” guys.

High “wasted”

Okay, guys, this is getting out of hand now. High-waisted pants on men? It’s more like high-risk fashion territory. We love a good throwback moment, but this isn’t it. Imagine stuffing your shirt into mom jeans – that’s the vibe you’re giving off. And it’s not attractive.

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Please leave the high-waisted wonders to the ladies. And for the love of all things stylish, please don’t tuck in your shirt if you take the plunge. It’s a full-on fashion faceplant waiting to happen. Here’s our number, thank us later for not making you look like a fool in front of everyone.

Canvas slip-ons, yes or no?

These things are the Crocs of the shoe world: dirt magnets with the aesthetic appeal of a soggy waffle – you could call them “canvas slop-ons”! This is the shoe of choice for, well, nobody who cares about shoes and their get-up, dignity, and reputation.

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Since these look as stylish as a dropped sock, you must level up your foot game. Even a spiffy pair of flip-flops (though we’re not exactly recommending those either) would be a fashion upgrade. Make the ladies happy, will you, and save yourself from embarrassment.

Grown men in crocs

Crocs on dudes? Buddy, you’d look more put-together wearing socks inside out. Those glorified clogs belong to toddlers or people who vacation in their driveways, not grown men. Even fuzzy bunny slippers (though not ideal) would command more respect. Forget we said that. We’re not recommending the latter either.

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Think of Crocs as the super lazy participation trophy of footwear. Those holey boys ain’t precisely sending a “sharp dresser” message. Maybe go barefoot? At least then, you could claim you’re one with nature, not one with questionable footwear choices.

Shark-tooth necklaces

A red flag in jewelry-loving men that you, girlie, need to look out for: Shark tooth necklaces, fellas! It’s more like an “aww snap” fashion blunder if you ask us! Those chompers belong on the ocean floor, not your neck. And they aren’t your biggest point of brag party either.

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It’s as cool as finding a seashell in your ear after a swim. These things haven’t been cool since Zubaz pants. Trust us, a real woman wants a man who can charm a shark, not just wear its leftovers around his neck. Step up your jewelry game and aim for sophistication.

Patterned suits have to go

Okay, this looks like a flowery disaster waiting to bloom. We’re talking giant, black and white blossoms that look like your grandma’s curtains exploded on your body. Tiny, tasteful patterns? Maybe. These monstrosities? No way! This has to go immediately.

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Ditch the giant, black-and-white nightmare if you’re auditioning for a role as “Grandma’s couch” in a fashion show. Leave the blooming bouquets for the wallpaper, fellas. A classic suit or a subtle pattern shows you have more style than a rogue dandelion.

Accessories overload

Chill with the bling! We get it; you wanna look like a million bucks, but piling on accessories like a pirate king is more “bling overload” than the “GQ model.” A watch and maybe some cufflinks – that’s all you need for it. It’s easy to go overboard, so keep this advice in mind.

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To show that you’ve got your fashion game on point, looking like you raided a costume shop jewelry box isn’t a flex and isn’t helping. Keep it simple, and keep it classy. Less is more, and your fingers will thank you for it.

Dental hygiene is not optional!

Ah, the elusive toothbrush – a tool seemingly abandoned by the male species. You may not see it, but skipping the morning scrub turns your smiles into a questionable shade of yellow, transforming the once charming grin into a potential biohazard.

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It’s not just unsightly; it’s a recipe for romantic ruin; it brews faster than a skunk at a perfume convention. Save yourself the embarrassment and invest in some toothpaste – your teeth will thank you, and so will anyone within sniffing distance of your fresh, minty breath!

Grooming is for men too

Scraggly beard, unkempt hair, and eyebrows that look like they’re auditioning for a bush league mustache competition? Come on, fellas, looking like you wrestled a badger and lost isn’t exactly a turn-on. Hit the shower, grab some tweezers, and maybe even a face wash.

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A quick trim, a splash of moisturizer (seriously, it’s not lotion!), and a nose hair eviction notice are all it takes to shave ten years off your look (and maybe win back that comb you haven’t seen since ’99). Trust us, a little self-care goes a long way. 

Human sculpture

Dudes, it’s time to ditch the hair product! We get it; you want that perfectly sculpted ‘do, but looking like a human grease sculpture isn’t the answer. But a glob of gel and a cloud of hairspray screams “helmet head” more than “effortlessly cool.” 

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A fistful of gel isn’t going to tame your mane. Less is more in this case. And for the love of good hair days, use the right stuff. Going to a rock concert? Grab the gel. Channeling your inner surfer? Hairspray might be your friend. 

Sunglasses mania

Let’s discuss sunglasses. Just because they’re trendy doesn’t mean they belong on your face. For once, consider your face frame and the time of the day before you perch those weird round glasses on your nose bridge. Not everyone can rock that look.

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Sunglasses should complement your face, not turn you into a bug from a bad sci-fi movie. Unless you’re dodging paparazzi, ditch the shades indoors and let your eyes do the talking. A confident gaze is way cooler than a face hiding behind the wrong sunglasses.

Hats off!

Hold on to your fedoras, fellas, because this fashion faux pas might blow your trilby right off! Hats? In this economy? Unless you’re Indiana Jones on a treasure hunt (and even then, maybe rethink it), boys, you need to ditch those bowler hats and fedoras.

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Once upon a time, hats were all the rage. But seeing a bowler hat in the wild is rarer than a compliment on your socks. Sun hats or baseball caps for summer? Sure, go nuts! But fedoras, beanies, or anything that makes you look like a character from a period drama are a big no.


Dudes, ditch the “shirt” that looks like a confusing fever dream. Is it a tank top or a fishnet? We have no idea, and frankly, neither does anyone else. A barely-there tank top made of cobwebs? We’re all for expressing ourselves, but there’s always a time and place, and this isn’t the best way.

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Is it casual? It’s more like casually horrifying everyone around you. This see-through net situation doesn’t belong at the gym, the club, or the grocery run. Its only purpose is to leave everyone wondering what fashion crime you committed and the appropriate punishment it entails.

V-neck overboard

It’s time to throw away the V-necks that make you look like you’re auditioning for a starring role in “Cleavage Canyon”! A subtle V-neck is cool, but one that dips south of your navel is plain wrong. You’ll be collecting more stares than compliments.

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Trust us, people won’t be admiring your well-defined pecs (or lack thereof) or your grizzly bear hair. It’s not a good look. Keep your chest hair a mystery and your necklines under control. You better stick to a classic crew neck or a less dramatic V if a V is a must.

Big, bold, and bad

Here’s the thing about T-shirts that double as billboards for your questionable sense of humor: those giant slogan tees that read like a lousy bumper sticker are more cringe than cool. “I Paused My Game for This?” It’s more like, “I Paused My Fashion Sense for This Shirt.”

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Small logos are ok, but those giant slogans usually land with a thud. Trust us, the only thing pausing is your chance of making a good impression. Leave the bold statements for your dating profile, and go for a classic T-shirt that says “effortlessly stylish” instead of “stuck in a teenage angst phase.”