1. "Skinny guys should wear boot cut [pants] to make their legs look wider." -macadocious
This could not be further from the truth. Boot cut is the most unflattering of all pant cuts for skinnier dudes. It won't make your legs look any bigger, but the flare in the bottom of the leg will make you look sloppier than a straight or skinny cut pant.
2. "Shirts were supposed to be baggy in the shoulders and chest." -utilitym0nster
Shirts aren't supposed to be baggy. They're supposed to fit! A good rule of thumb is to get a shirt that fits as close to your body as you can while you retain free range of movement in your arms.
3. "I thought that wearing the right clothes would automatically mean that I'd dress better." - Poizar
A common misconception is that dressing up is the equivalent to dressing better. In fact, the two are completely unrelated, and a man in sharp casual wear will look better than a man in a sloppy suit every time.
Additionally, you should always be mindful to dress appropriately for the situation at hand
4. "I thought showing off you have money to buy 'high fashion' mall brands meant I was fashionable and looked good." -PSIKevin
Many "prestigious" mall brands are perceived as "quality," while they actually sell completely overpriced, poor-quality garments covered with gaudy branding. Labels like Abercrombie and Fitch and Armani Exchange are two of the biggest offenders.
Learning which brands to avoid and which brands are worth their price is a crucial step on the road to dressing better.
5. "Shorts are dumb and should only be worn by boys under the age of 12 or sportsmen." -themanifoldcuriosity
Most men are now aware that shorts are perfectly fine to wear in the warmer months, and even acceptable in some more casual office environments.
Just avoid the dreaded cargo short.
6. "Cargo shorts were cool because of everything you could fit in the pockets." -Adjustify
Again, cargo shorts are generally looked upon today as extremely passé and dated. Avoid these at all costs.
Instead, try a slim chino for a more modern look.
7. "Only construction workers and goths wear boots." -GDDesu
There's a wide variety of boots available, from brouged dress boots to vintage reproduction work books. There's a boot for every kind of man: not just black Dr. Martens and Timberlands.
8. "I thought boat shoes were the most fashionable shoes." -UnbiasedOnionRing
Boat shoes are still a great choice for summer footwear, but they are far from being the most fashionable shoe out there.
There are however, plenty of other choices available.
9. "I thought square-toed shoes were cool." -TummyDrums
Square-toed shoes haven't been acceptable for a while now, and men are urged to stay away from them. They are clunky, awkward, and distracting, with a completely unflattering profile.
Stick with your classic wing tips and Oxfords.
10. "I used to color coordinate my shoes with my shirt to make sure they were the same color." -Yeaga
While it can be a strategic style decision to make your shoes and shirt match, it is pretty much completely unnecessary.
In fact, for most outfits, this would look pretty ridiculous. It can work well for some street style outfits based around specific kinds of sneakers, however, but maybe wait to try this look until you get your fashion sea legs.
11. "I always thought the belt had to match shoes no matter what you were wearing." -WhoopItIsThere
Matching your belt and shoes is a good rule of thumb for the dressiest of occasions, but that's really the only time. It's not necessary for business suits or any level of dress lower than that.
12. "Black shoes went with everything." -KlausFenrir
Black shoes don't go with everything. For many colors of suits and other outfits, it would be very "fashion forward" to opt for black footwear.
If you want a shoe that goes with everything, buy a nice medium brown brogue.
13. "Pocket squares have to match your tie." -vim_all_day
Contrary to what you see news and sports anchors wearing on TV, pocket squares do not have to match your tie. In fact, they probably shouldn't.
If anything, your pocket square can match the color of your shirt, but even then it's not necessary. Feel free to branch out with your pocket square.
14. "I believed black suits to be the most versatile and best color of suit to buy." -Rerrgon
Actually, the most versatile color of suit is navy or charcoal. These are the first two colors men should buy suits in when they're starting to build their wardrobe.
Black suits are only suitable on occasions like weddings and funerals, and sometimes for the office. Use your black suit sparingly.
15. "I thought argyle sweaters were the height of fashion." — reddit-er
Argyle sweaters, while not super egregious mistake, have been securely out of fashion for a while now. The pattern just looks too old-school to fit into today's styles.
Other patterned sweaters, however, are certainly in style — so don't be afraid of them altogether. We recommend them as part of our winter essentials guide.