How to Dress Up For Failure: 10 Obvious Fashion Mistakes Most Men Make

By Patrick Banks

Posted 3 years agoOTHER

There are two types of men in this world – those with an innate sense of style who are always impeccably put together, know their audience and dress the part, and those who completely, well, suck at fashion. Luckily for the second type, there are plenty of ways to fix that. The trick is realizing and acknowledging your style mistakes, which again, many men don’t and that’s where we step in.

If at least five of these ring a bell, you’ll finally get the epiphany and hopefully fix your mistakes. It’s time to face the music – your fashion choices speak volumes of your personality, so in order to make a good first impression, get the job, get that second date, you’re going to have to step up your game, so read on and see where it all went wrong.

1. The ultimate crime

Ok, let’s start with the worst. Yes, women can get away with wearing cute socks and sandals, men can’t – end of discussion. Socks and sandals combo is the ultimate women repellant. Ok, sometimes women get it wrong as well, so who are they to judge but, in all seriousness, no matter how well certain dudes pull the look off on the runways, there is no way you can pull this off in real life. If you’re going to wear Birkenstocks, make sure the feet are bare. There is an abundance of cool shoes that deserve socks, but sandals aren’t one of them.

2. Holding on to the past

The hipster is dead, if he ever truly existed, so stop being a member of a crowd that is extinct and start dressing like a real man. Yes, the whole hipster phase was cute and actually appealing for a nanosecond, but it’s time to be a grownup and develop a sense of style that is actually authentic and not ‘authentic’ in the sense that half the population is rocking it.

3. You overdo it

Whether you’re underdressed or overdressed is irrelevant because both approaches are wrong. When you’re seriously underdressed and borderline sloppy-looking, no one will take you seriously. On the other hand, if you try too hard you end up looking like a hot mess but in a diametrically opposite way. The key is to find this golden middle – keep things simple. Know which colours do you justice, make sure the clothes fit perfectly, follow trends that go along with your personality and that’s pretty much the gist.

4. Suit up


Unlike the previous generations, the younger ones simply don’t suit up, almost ever, not even to a wedding. While you don’t need to be Barney Stinson and have a suit arsenal in your wardrobe in order to look great, there are times when you definitely need to suit up. Wedding, important meetings, formal events – these all call for a suit, not that men’s suits can’t be rocked on an even more regular basis. After all, women love a man in a suit, so if you want to dazzle, dress to impress.

5. Not caring about fashion trends

We’ll give you Hawaiian shirts and socks with sandals – these were spotted on the runways along with pastel suits. Designers sometimes put the strangest, borderline ugly things on their models, and we’re definitely encouraging you not to follow every trend. However, just because you’re not supposed to fall prey to every trend, doesn’t mean you shouldn’t embrace certain ones that actually look good and will in fact refresh your wardrobe and give you a little style boost. For instance, the athleisure trend is awesome, and if you play it right you can pull it off for any occasion. Hey, you can even follow weird trends as long as you have the confidence to pull them off. The point is, there are amazing trendy pieces out there that have staying power, you just have to see which ones make you feel like yourself and you can rock whatever you want.

6. Not caring about details

Perhaps you’re blind to details, but women most certainly aren’t. They will scan you from head to toe, and even if you’re not trying to impress your date, you should still put in a little effort. Make sure your shirts are pressed, that your colors are coordinated, that you’re wearing the right shoes and that you add a little something to finalize your look like a great perfume and a killer watch. Style isn’t just about clothes, it’s about the little things that glue the whole thing together.

7. You’re a cheaposaurus

No one wants to spend $70 on a regular white T-shirt, and of course, this kind of spending is ludicrous. However, a nice crew sweater, a couple of quality button downs, a trench, a leather jacket, great jeans, good footwear as well as quality outerwear – whether you’re a jacket or a coat type of guy – these aren’t the things you want to cheap out on. First of all, they’re not called investment pieces for no reason – they will last you a long time simply because they’re made from superb fabrics, and secondly, they will always be in style – hence, you will always look good wearing them. Regular tees, hoodies and sweats you can save a buck on, but these basics deserve to be paid the asking price.

8. Not dressing for your body type

You may or may not have seen Crazy, Stupid, Love, but the story goes, wife leaves husband, husband meets a suave guy at the bar (Ryan Gosling), suave guy gives the poor dumped guy a makeover and makes him realize that he’d been wearing the wrong size of everything his entire life. Know your body, and make sure your clothes fit properly. If you don’t know how to do it, consult a tailor or a fashion-savvy friend.

Do everything, just stop looking like you’re wearing a potato sack. So, make sure your pants are the right length, as well as your sleeves. And please, oh please, iron your clothes. Nothing can ruin an otherwise perfect outfit than the fact that you look chewed up and spat out.

9. Accessories

Aside from perhaps a ring or a subtle chain or a watch which matches well with your lifestyle, most men can’t and shouldn’t wear jewelry. Perhaps there are tattoo and piercing artists that can pull that look off, but even they do it because it’s part of their personality. The rest of us should keep things super minimal in this department – you’re not a rap star, leave the bling to those who are.

Final mistake

The wrong haircut can ruin your entire face, so visit a good salon where you’ll get the right advice on what kind of hairdo suits your face shape, but we’ve crossed over to a whole new arena here. Grooming is a different topic, so perhaps we’ll discuss it some other time. For now, take care of that wardrobe of yours and go get ‘em.


About the author Patrick Banks

Patrick is a Berlin-based dating advisor, motivational speaker, a huge fitness and vegan diet enthusiast and the main editor at Wingman Magazine, specialised in men's health. His ultimate goal is to share with men around the world his passion for self-development and to help them to become the greatest version of themselves. He believes a healthy body and successful social interactions are two main keys to happiness.