The other day, my friend was super upset with me because he watched one of my videos where I said an Apple Watch wasn’t stylish. I asked why he was mad at me because I was telling the truth, so we debated Apple Watches. I equate the Apple Watch to the Tesla for cars. If you’re a car guy, you’ll never rock a Tesla. If you’re somebody stylish, you’ll never rock an Apple Watch.
The conversation went further, and I asked him why he cared anyway. I’m a 48-year-old dude with an earring, so take everything I say with a grain of salt. That said, here is my list of items men should never wear in 2025.
And just a quick note: Make sure you wear clothing that fits your body. Get rid of anything too big, blousy, or baggy, or that doesn’t fit correctly (too tight).
Ditch these ASAP
- Air Force Ones. These shoes are the most overhyped and overplayed of 2024. I’m sick of seeing them, and I don’t think they look that good. I don’t love the profile, and if a 12-year-old girl can wear them, you, as an adult dude, should not. A better option is a white leather casual sneaker. I like the brand Axel Arigato in the Dice Lo style.
- Fashion hats. Fedoras were huge about 12 years ago, and then there was a flat bill-type cowboy-style hat that I thought the dudes looked douchey wearing. Then there was the beanie pulled-back phase. If you’re a dude that wears beanies rolled up, it’s not stylish.
- Crossbody bags. I’m sick of them.
- Ill-fitting denim. Whether it’s denim that’s too tight or denim that’s sagging down off your booty, you need to stop it. Wear jeans that fit correctly—not too big, too baggy, pulling, or puddling down at the ankles. This also goes for jeans that are overly distressed or a color other than blue, black, grey, or white in the summer.
- Fake leather. Fake leather sucks whether it’s a jacket, sneakers, boots
- Dad shoes. They do not make you look sexy.
- Ankle socks. What’s the point of these? If you want to wear socks, either go no-show or mid-calf. Go for something aesthetic and more stylish. Ankle socks suck.
- Tattoos. It’s alarming how many men and women are following this trend and covering their bodies with lots of tattoos. Most of these tattoos aren’t that great or pretty. They’re stupid.
- Inappropriate clothes. Stop wearing any t-shirts or socks that have inappropriate language or something stupid on them.
- Pointy boots or shoes. You should know better by now.
- Shiny shoes with jeans. Nothing makes you look like you have zero style more than shiny shoes with jeans. Make sure your leathers match if you are wearing dress shoes and a belt. You can’t have a beat-up belt, either.
- Tacky belts. Ensure you’re responsible with your belt, and do not wear big buckles or beat-up belts. Belts that yell, “Check me out! I spent way too much money!” should also be avoided. They are too showy and not needed. Anson Belts are the best option all the way around.
- Flashy items. If you have any loud and flashy items, you can do better. People who want all the attention for being stylish do not wear loud and bright logos, patterns, and flashy items.
- Dress shirts untucked. Dress shirts are meant to be tucked in. If you want to wear a button-up untucked, make sure it’s designed to be untucked. It will be shorter and not down past your crotch.
- Button-down collar. You will look stupid wearing a button-down collar with a tie and a suit. Don’t do it.
- Thin lapels.
- Thin ties.
- Suit bling. If you want cufflinks, that’s cool. If you want to do a white pocket square, that’s cool. But all of the matching tie and pocket square combos with flowers in the hole and lapel pins make you look like a loser. Also, too much matching doesn’t look good. Go for a minimal, clean aesthetic.
- Long shorts. Don’t wear shorts that come down past your knee. Also, basketball shorts look stupid.
- Not wearing underwear. You can see your weiner without underwear. Don’t do it at the gym or out and about because it’s ridiculous.
- Under Armor shirts. It doesn’t matter if you’re ripped or not, they are too tight. This goes for any overly tight pieces of clothing. It’s not a good look.
- Piercings. If you’re wearing a face full of piercings, you look trashy. Do better. If you have gauges, it doesn’t necessarily make you look sophisticated. People have perceptions of others with a lot of piercings and tattoos. You want to make sure you have every opportunity in the world.
- Jacked-up underwear. Don’t wear big boxers that do not offer support or sexiness. Wear boxer briefs or something a little tighter. If your underwear has holes or is stained, get rid of them.
- Yellowed T-shirts. If your T-shirts are stained, get rid of them. The same goes for dress shirts with pit stains.
- Muffin tops. If you wear shirts tucked in and have a big muffin top, size down.
