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Want to know the fastest way to ruin a perfectly good bike ride?
Wear the wrong thing.
I’m not only talking about minor fashion slip-ups here – I mean the kind of clothing choices that can send you flying over your handlebars or leave you walking funny for days (or not).
These aren’t just style fails; they’re cycling survival lessons written in chafed skin and torn dignity.
Flip-flops (Unless You Hate Your Toes)
Whoever first thought, “I’ll wear these thin pieces of foam secured by a toe thong while operating a moving vehicle” clearly never experienced the joy of a flip-flop getting mangled in a bike chain.
These summer “shoes” are cycling suicide—they slip off pedals, offer zero protection from road debris, and become downright dangerous in sudden stops.
The worst part? When it rains, they transform into slippery death traps.
Your feet (and face) will thank you for choosing real shoes.
🤔 I think sandals (so basically more secure straps) can be OK for very (VERY) casual rides. There’s also the option of sandals with cleats.
Read more: Best cycling sandals
Dark Clothing at Night (Probably Better To Be Seen!)
Wearing dark clothing while cycling at night is basically playing hide-and-seek with cars—except you’re the only one who knows you’re playing.
Even with decent bike lights, dark clothing makes it tough for drivers to see you until they’re dangerously close. This is especially true on poorly lit streets or during bad weather.
Sure, that black cycling kit might make you look sleek and professional during the day. But at night, it could be the last outfit you ever wear.
🤔 If you must wear dark clothes, then try to at least put some kind of reflective band or socks on your legs. Because the legs are always moving it is more likely to catch a driver’s eye than a stagnant reflective item of clothing.
I know reflective gear isn’t always the most fashionable choice, but it’s better than becoming another roadside statistic.
Headphones That Block All Traffic Sounds (Death Wish Much?)
Blocking out all external noise while cycling is like voluntarily giving up one of your most important safety senses.
Those noise-canceling earbuds might make your playlist sound amazing, but they also silence crucial traffic cues like approaching vehicles, emergency sirens, or warning honks. Even the sound of a car’s engine can tell you a lot about its speed and direction.
Your favorite workout mix isn’t worth the risk of missing a critical audio warning.
If you absolutely must have your tunes, consider using just one earbud or try bone-conduction headphones that keep your ears open to surrounding sounds.
⚠️ I don’t normally wear headphones, but when I do (off-road or very safe and quiet roads), I use bone conducting headphones so I get the best of both worlds.
I would recommend NO headphones when riding in heavy or fast traffic
100% Cotton on Long Rides (Welcome to Sweat Central)
Cotton….
What starts as a comfortable shirt quickly becomes a sweat-soaked nightmare that refuses to dry. This is especially true under a backpack or in humid conditions.
Your body produces sweat to cool you down, but cotton traps it against your skin, defeating the whole purpose of sweating in the first place.
The chafing alone is enough reason to ban cotton from your cycling wardrobe forever.
Super Short Shorts Without Padding (Your Bottom Will Thank You Later)
Those trendy short shorts might get you likes on social media, but they won’t make friends with your sensitive areas.
Without proper padding, every pedal stroke becomes an exercise in endurance—and not the good kind. Your inner thighs will quickly remind you that friction is not your friend.
💭 For really short casual beach path rides, short unpadded shorts are just fine. The more miles you rack up, the less I say the are just fine.
The human body wasn’t designed to sit on a small piece of leather or synthetic material for hours.
Save the cute shorts for after your ride, when you’re not bouncing on a bicycle seat.
Heavy Jeans on Hot Days (Say Hello to Sweaty Chafing!)
Jeans and hot-weather cycling go together like sandpaper and sunburn.
The combination of heat, sweat, and rough denim creates a perfect storm of discomfort that gets worse with every mile. Your legs essentially become steam ovens wrapped in stiff, unforgiving fabric.
Even a short ride can turn into an endurance event when you’re fighting against heavy, sweat-soaked denim.
👖 Remember: just because you can ride with jeans on, doesn’t mean you should—especially when the mercury rises.
That Old Helmet From 1995 (Your Brain Deserves Better!)
Helmets have expiration dates for a reason.
My bicycle helmet from the 90s, it’s still hanging up in my parents’ utility room
byu/Kramit2012 in90s
That vintage 90s helmet might match your retro bike perfectly, but its ability to protect your brain expired somewhere around the time of dial-up internet.
The foam inside degrades over time, becoming brittle and less able to absorb impact – even if it looks perfectly fine from the outside.
Helmet technology has advanced dramatically in the past decades.
Modern helmets are designed based on current research about how brains actually get injured.
Shoes With Laces That Party Outside Your Pants (Potential Chain Tangle Disaster)
Letting your shoelaces flow freely while cycling is like playing Russian roulette with your feet.
One moment you’re cruising along, feeling great about life. The next, you’re performing an impromptu gymnastics routine because your laces decided to tango with your chain.
👞 I only wear laces on very short casual rides, as I prefer dedicated shoes. If I am wearing laces, always look down after I start and if there’s any loose laces, I get straight off the bike and tighten them up,
Your bike’s moving parts are constantly looking for something to grab, and loose laces are like an all-you-can-eat buffet for your chain.
The ten seconds it takes to secure your laces could save you from a world of pain and embarrassment.
Don’t learn this lesson the hard way.
Skirts Without Shorts Underneath (All It Takes Is A Gust Of Wind)
Freedom of movement doesn’t have to mean freedom of exposure.
A skirt alone offers the worst of both worlds: it can tangle in your chain, catch on your seat, and reveal everything you’d rather keep private.
The simple addition of bike shorts underneath transforms this liability into a perfectly acceptable cycling outfit:
The wind has impeccable timing for maximum embarrassment.
The memory of accidentally flashing an entire bike path lasts longer than the ride itself. Especially in the age of social media!
White Pants Near Chain Grease (They Won’t Stay Pretty For Long)
When it comes to white clothes, bike chain grease is basically permanent marker in liquid form.
The laws of the universe dictate that the cleaner and more expensive your white pants, the more magnetically attractive they become to chain grease.
Managed to dirty my new, white pants on my bike chain! Any suggestions as to how to remove it?
byu/Rare-Option1714 inCleaningTips
The dark, stubborn stain appears with just the slightest contact—often without you even noticing until it’s too late.
Chain grease doesn’t wash out with normal detergent.
Sandals With Socks (The Ultimate Crime Against Fashion)
Not all fashion crimes deserve jail time, but this one might be a felony 😂
We talked about sandals being better than flip-flops for safety (and they are), but with socks? Guilty as charged by the fashion police LOL.
I think if bike touring, sandals and socks gets a bye. Comfort is everything when you’re cruising long distances.
Sandals with socks on a bicycle announce to the world that you’ve completely surrendered to practicality over dignity.
Fellow cyclists will pretend not to see you. Pedestrians will cross the street to avoid association.
What did we miss? Are there any other clothes or accessories that should not be worn?
Tell us about them in the comments below 👇
Gloves…fingerless or not. Protect your hands if you go down. Eventually you will