25 Items that Make You Look BORING! 

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Not wearing a watch. A watch is the greatest accessory for a man. But this isn't the solution if you're wearing a technology watch. You will look average in basic in it. Take 30% off all Aura watches and straps (41mm, too) with code AlphaM.
No accessories. Accessories can elevate your style and make you come across better aesthetically. Whether a ring, bracelet, watch, or corn necklace, you can set yourself apart.
Dad bod. There's nothing sexy about a dad bod. If you want to look great out of your clothes, you need to work out.
No facial hair. If you don't have anything on your face, you will look soft and doughy unless you have super strong features. Also, don't cut off your sideburns. Sideburns help frame your face and finish your hairstyle unless you have a bald fade.
Hats 100%. If you wear hats all the time and in every environment, it's a thumbs down.
Visible undershirt. If you can see it, it's bad.
An untucked dress shirt that's too long. If your dress shirt is coming down past your crotch, you look boring and basic because that's what boring basic dads do. Remember there's a difference between casual shirt designs that are meant to be untucked and dress shirts that you're supposed to wear tucked in.
Sports paraphernalia. If your shirt has a logo, like a college sports team, it's boring and basic. Sports paraphernalia doesn't make you look stylish.
Boring shoes. Boat shoes, bad athletic sneakers with anything other than athletic wear, and dress shoes with sneaker bottoms are all thumbs-down.
Clothing that doesn't fit. You need clothing that fits your body. Don't wear baggy clothing, baggy suits, or anything else oversized. You need clothing that gives you a style hug. Also, untapered pants should be tailored and tapered. Whether jeans, khakis, or chinos, they should not bunch at your ankles. And regarding shirts, always look for a slim fit. You shouldn't wear skin-tight shirts, but they should not be cut boxy.
Tighty whities. Basic underwear and boxers get thumbs down. If you want to go boxer brief, black is okay.
Pathetic polo shirts. Big patterns like stripes are horrible, and country club logos are also a no-go. Also, I'd like to add Tommy Bahama to the list. Certain brands, like Brooks Brothers, make you look boring and basic. If you know what you're doing at Brooks Brothers, you can be okay with it if you have clothing that fits properly and is coordinated (old-money aesthetic).
Not dressing for the occasion. You should always aim for one level up. If the levels are already up, like for a wedding or a formal function, you want to ensure your clothing is tailored.
Black shoes. Most guys wear black shoes because they are safe and match everything. Go for a brown pair, which is rich and rugged and matches pretty much everything except for a black suit, which you should be wearing anyway.
Black suit. There's no point or place for black suits. Go super dark charcoal.
HEYDUDE shoes. These are so bad they should be a sin.
Long shorts. You need to show a little bit of leg, so your shorts should be a few inches above the kneecap. If they're baggy, it's even more horrible.
Middle management business casual. This is boring as hell, whether a button-up shirt tucked into khakis or a polo on casual Fridays. They're all basically wearing the same button-up that is buttoned too high.
Too many buttons. You need to expose a little upper chest (aka man cleavage).
Bulky sweaters. Lightweight Merino wool sweaters that fit your body and are a bit more contoured should be your choice. Fabric matters. If the fabric is big and heavy or itchy and scratchy, it's no good.
New Balance shoes. Enough said.
Festive t-shirts. T-shirts with things on them, like an American flag for the 4th of July, are basic.
White ankle or fun socks.
Matching tie and pocket square.
No hair product. If you towel-dry and head out the door, you're out of style and basic.