How To Dress Sharp When NO ONE Else Does?

‘Why are you all dressed up?’

‘Think you’re better than me?’

‘Getting all fancy today, are we? What’s the occasion?’

Sound familiar?

How do you respond?

Perhaps you don’t know how.

Perhaps you feel RIDICULOUS, suddenly aware of how much you stick out.

You’re a single scrap of dapper in a sea of drab.

Experiences like this – especially early in your style journey – can really blindside you. How do you find the confidence to dress sharp when no one around you does?

Today I’ve teamed up with Raphael Schneider of The Gentleman’s Gazette to answer that question.

Raphael has a lot of experience being the best-dressed man in the room. He lives in Minneapolis and he’s often the only guy wearing an ascot, a bow tie, or even a necktie. He sets the standard when it comes to dressing sharp.

But a lot of men fear that someone will say, ‘What are you so dressed up for? Who do you think you are?’ Raphael gets that all the time – and he realizes that it can be hard to deal with. Here’s his solution.

#1. Find Your Why

Raphael’s first piece of advice is to ask yourself these two questions:

1. Can I be the best-dressed man in the room?

(Hint: YES!)

2. Why should I be the best-dressed man in the room?

For lots of very good reasons! When you dress sharp, you stand out from the crowd in a GOOD way. People notice you. They’re much more likely to come up and talk to you. They automatically think you’re smarter and more educated, and they have more respect for you.

Some people may be surprised by your style at first, but they’ll eventually see it as a part of you and come to expect it of you. Raphael is a man who’s not afraid to wear a suit to pick up some bagels. ‘People know me as the dress-up guy,’ he says. ‘When I go there right after the gym they’re like, “What’s going on? You’re not dressed up today!” ‘

But a lot of men fear that someone will say, ‘What are you so dressed up for? Who do you think you are?’ Raphael gets that all the time – and he realizes that it can be hard to deal with. Here’s his solution.

#2. Dress With Confidence

If you wear something smart, you have to own it and look effortless in it. It has to be part of who you are. There’s an Italian word for this: sprezzatura. Sprezzatura is the art of dressing with nonchalant elegance – embracing little imperfections like a crooked tie bar or a messy pocket square.

As with any new skill, dressing with confidence takes practice. Whenever I put a new outfit together I practice wearing it around the house. This way, my family can see it so I’ll know if it needs adjusting. If it’s a bit uncomfortable, I get used to how it feels and I’ll know what to expect.

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#3. Know What To Say

‘What are you dressed up for?‘ doesn’t have to start an argument. It can be the setup for a joke – or even for an act of kindness. Try these replies on for size:

‘It’s Thursday.’

‘I’m prepared for adulthood.’

‘I knew that I would meet a very important person today, and that just happened.’

Even if people are negative, try to take the high road and respond with kindness. This will usually shut down the conversation. They almost certainly won’t have a comeback ready, and you can go about your day.

It’s important to pick a reply that suits your personality. If you’re a serious guy, don’t respond by cracking a joke. If you’re more of a joker, go ahead. An out-of-character response just won’t feel genuine.

I find that if I give people a quick explanation – a bit about my career choice and where I’m going – they just accept it. That’s how people work. Even if you do something blatantly rude, like cutting in line, people are more likely to accept it if you offer an explanation. But don’t do that. It’s rude.

Finally, you’re very unlikely to hear someone say, ‘The way you’re dressing offends me.’It’s usually the other way round. People treat you better when you dress well, gentlemen. They give you compliments. They show interest. If they work in service, they may even give you special treatment. An extra shot in your latte. The last booth in a crowded restaurant. A hotel room with a spectacular view and a bottle of Champagne.

Bonus: Be Friendly

Worrying that dressing sharp makes you look arrogant is understandable. Raphael has a simple and brilliant solution: go the extra mile to prove that you’re not. Kindness and good manners are perfect accessories for any smart outfit.

Raphael uses his friendly personality to show people that he isn’t a snob. He says, ‘When I smile at people, that brings out the best in them. I may be dressed very differently, but if I can connect with them about a topic that they’re interested in, be it football or something that’s going on in their lives, they really respect that. They’ll say, “Wow, you’re a great guy. I want to dress like you.” ‘

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