First Impressions Matter: 6 Style Tips for Successful Male Entrepreneurs (at Any Age)

Making a good first impression is about more than “dressing for success,” whatever that means. Nor does it require fealty to the latest fashions. Successful male entrepreneurs understand the importance of timeless style at any age. Follow in their footsteps with these six tips:

  1. Dress for the Crowd

What flies in one setting falls flat in another. Before you dress for the day, review your schedule and prep accordingly. If you’re holding meetings with private equity wags all day, you’ll need to up your game. If you’re giving a lecture at your local technical college, feel free to go casual. Trust your gut.

  1. Mind the Eyes, Guys

Contrary to stereotype, entrepreneurship isn’t a young man’s game. That’s not to say you shouldn’t try your best to exude youthfulness in the arena, though. Applying men’s anti-aging eye cream every morning and evening goes a long way toward preserving that timeless crinkle, no matter what your birth certificate reads.

  1. Trim That Beard (or Let It Go)

Beards might be back in fashion, but that’s no excuse to embrace the wild man look. Keep your facial hair under control with a multi-use electric beard trimmer. If you’re having trouble keeping up or achieving the tastefully tame look you crave, start fresh after a full shave.

  1. Wear a Watch, Even If You Don’t Need to

21st-century entrepreneurship is all about pragmatism, or so we’re told. Time was when a sensible wristwatch was the epitome of pragmatism — how else could you possibly know that you were on track to make your next appointment?

These days, watches aren’t strictly necessary, in the sense that they’re the only personal possession capable of telling the time. But it’s impossible to overstate the cachet of a sleek wristwatch — digital, analog, or smart. No need to spend a fortune, but do bear in mind that nothing quite exudes quiet confidence like a fashionable timepiece.

  1. Send a Message With a Leather Messenger Bag

Unless you’ve invented a time machine to spin back to Palo Alto circa 2007, that oversized backpack needs to go. Now. Switch it out for a sedate leather messenger bag that looks and plays your age. You’re grown up, you’re out of the house, you’re running your own company, for goodness’ sake. It’s not like you can’t still bike to the office with your bag slung over your shoulder.

  1. Belt It Up

Last, but not least: don’t forget to belt it up. Even if you’re hopping on the tuckless shirt bandwagon (no judgments, if you are), you’ll want a sturdy, stylish leather or cloth (careful!) belt that draws the eyes without making a scene. Bonus points for a belt that actually, you know, matches your shoes.

Your Style Is Your Personality — Wear It Proudly

You don’t need to be told twice that you only get one chance to make a first impression. You know this.

What you might not realize is just how powerful an asset your distinctive style can be. Your personal style is an extension of your personality; while one pocket square doesn’t a complete man make, you surely feel more confident with that ready-for-business look than without.

So, wear your look with pride. The only thing better than making a good first impression is leaving a lasting one.

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