Pest's Pads: Cheap market item that fits a few sets, the person that wears this is not doing it for profit and they just like the way it looks.
Team Player: You do not wear this. Well, now you do so you can complain but honestly I have not seen a soul wear this since it came out.
Throttlehead: Biker scout. You're making the biker scout and you might even be edgy.
Chaser: This is the "Everybody wears it now" cosmetic from summer 2022. I've seen more people wear it since it came out than people who don't.
Barefoot Brawler: You're a silly little guy, you. Making jokes and all that. You suck with your pipe aim though.
Combat Casual: If you're wearing this, you either are wearing it with the Squatter's Right too or it's strange and you have it paired with other strange cosmetics. There is no other reason to not equip the Squatter's Right with it and it only looks good with the Squatter's Right.
Western Wraps: You use the frontier justice and gunslinger and you purposely set up on hightower because you know it'll make somebody mad. Thought I was going with the western engi set? Well yes, they normally do wear it, but they're annoying.
Hawaiian Hunter: You have this in strange or unusual form. I have seen 4 unusual Hawaiian Hunters as opposed to 0 normal Hawaiian Hunters.
Tactical Turtleneck: This is THE definitive "great cheap cosmetic" that everybody agrees upon. I have seen nobody express their distaste for it, it's all good comments.
Undercover Brolly: Cheap unusual form. You DO NOT wear this. It's so ugly that even trolls won't wear it. Should be removed.
Boston Brain Bucket: You unboxed this and wear it so you don't feel like you wasted your money. You did.
Ripped Rider: Edgy scout misc. You're probably using stock scattergun, pretty boy's pocket pistol, and the boston basher and you will pee yourself if you ever see a friendly, even on a friendly server.
Detective: You have the detective soldier loadout. That's it.
Hawaiian Hangover: You have the pooped deck and you are GUARANTEED to use it after a random crit grenade kills 4 people pushing the cart on Upward.
Squatter's Right: Combat casual stereotype except this one actually fits with other cosmetics.
Lawnmaker: You are a good but not great engineer that uses fun weapons over the meta and your favorite map is probably Barnblitz.
Fizzy Pharmacist: This is a trader cosmetic. Traders wear it with a medic unusual because it looks good on pretty much anything.
Tropical Camo: You're a sniper on a trade server that makes no exceptions for anybody. You will completely lock down the server and everybody will hate you for it.
Kazan Karategi: Expensive! You wear it with that one flame fighter cosmetic from like 2020 and you spam the fireball taunt whenever you get the chance. Around the corner? HADOUKEN! Spawn doors? HADOUKEN! Enemy teleporter in your base? HADOUKEN! God!
Head Banger: Human sentry buster, will do literally ANYTHING to destroy a sentry nest, and will probably succeed. Brave people they are.
Soda Cap: You're a new player that got a pretty good unbox so you're keeping it.
Monsieur Grenouille: You're that one spy in ever trade server that is completely AFK and has been AFK for around 12 hours straight. When you aren't AFK, you are the best damned gunspy the server has ever seen.
Night Vision Gawkers: The NEW observer look. Has caused a split between tradionalism and modernism in the observer spy community. I'm seriously not joking.
Rocko: Friendly server player and fairly nice guy. They just kind of chill. Note: NEVER break the no-kill rule on a friendly server when one is in it. They WILL dominate you so bad you won't touch TF2 for 3 weeks.
Decorated Veteran: DAMN YOU'RE RICH! Anyways, I've only ever seen a spy wear it and the spy in question also had a burning flames unusual, so yeah.

Imp's Imprint: Pretty good scout misc. You'd think it'd be an edgy cosmetic but there are far more aggressively edgy cosmetics in this case.
Firearm Protector: You're wearing this with the other cosmetic. That's it, there is literally no other situation I've seen somebody wear it in.
Bombard Brigadier: Cool stuff. This cosmetic is worn by demoman they have good pipe aim but still insist on using stickyspam, which will get them killed, a lot. Usually worn with the Whiff of the Old Brimstone.
Nightbane Brim: Great cosmetic that you will wear for the rest of October and then not until next October because it doesn't fit much non-Halloween stuff.
Horror Shawl: BOO! Did I scare ya? Also, edgy.
More Gun Marshal: Heavily underrated cosmetic that actually has pretty cool styles. Instant woman magnet if you wear this, you absolute Chad.
Hunting Cloak: Edgy sniper cloak! Wear this with the chronomancer and the hat that shall not be named.
Turncoat: The most solid and general Spy misc since the Business Casual. Also 50% chance the spy wearing this is a great gunspy.
Beaten and Bruised: I love this. All-class FIVE STYLES! For cheap, too! We should artificially inflate the price of this.
Starlight Sorcerer: I think there was a stereotype for the camouflage pajamas for sniper a while ago, something about listening to music waiting for something to kick in. This is exactly that, word for word.
Masked Fiend: Edgy.
Safety Stripes: Only worn with the Firearm Protector, even though it's fine on its own.
Road Block: You're also wearing the Road Rage.
Dustbowl Devil: Western engi with a hint of EDGE. Probably uses the Black Dahlia pistol instead of the normal one.
Lavish Labwear: Just a very solid medic misc. It's nice. Also wearers of this use the Vaccinator.
Headhunter's Brim: The next step on the stairs to full edge. Why do sniper mains take themselves so seriously?
Cranial Cowl: Excellent soldier hat. Also, edgy joke.
Alcoholic Automaton: I don't need it, I don't need it... I NEED IT!!!!
Road Rage: Mad Mask but worse.
Victorian Villainy: You use the overdose and that one medic melee that shows enemy health, and you only do it for the sake of using non-meta weapons.
Propaniac: Flame mohawk. Reminds me of the Bunsen Brave.
Onimann: *Que Linkin Park*
Fire Breather: Furry.
Magical Mount: Pony Express for Pyro. Pyros using this also use the Pyroland Decorated Weapons.
Misha's Maw: It finally got in! New friendly heavy hat. Also furries, but less than Fire Breather.
Cabinet Mann: Like the Beep Man, but for nostalgists.
Pony Express: Ladies and gentlemen, it got in. Good day.