The Young Man’s Guide to Looking Smart

I remember my first corporate job interview. I showed up wearing khakis and a button down shirt. I sat across from a gentleman wearing a suit; he looked suave like he had important things to do. I recall thinking that there was no way I had the job, this “suit guy” was going to get it. I was twenty at the time.

As it turns out, we both got the job. Danny and I worked together for five years. During that time, he taught me a lot of lessons that, at the time, just annoyed me—but now I see them for the nuggets of wisdom they were.

“Dude, tuck in your shirt. Are you a fucking slob or something?” He said that one to me a lot. Danny once walked over to me, at his own wedding,  from a group of people, pulled me to the side and said, “Dude, flip your collar. That's not how you wear a tie, you bozo!” He fixed my tie up and walked away.

Danny was a central figure in my life for the time we worked together, I learned a lot about how one ought to carry themselves. I find myself doing the same here and there with my younger friends. Danny was about ten years older than me, I should mention.

You're a young man, but that doesn't give you an excuse to dress like a chump. What follows here are some tips to think about when dressing for the day, your job, and life in general.

Footwear Counts

More than what is given credit for, smart footwear creates a great first impression with people. It's not about the money that makes for a good pair of shoes either. So don't blow your wad on the best pair of shoes you can afford.

Consider your tastes but also avoid a few common offenders. Avoid sandals, unless you're at the beach. Sandals can be a turn-off and make you seem casual—which is fine, but if you're trying to make a strong impression just say know to flip-flops. Also, avoid torn and tattered shoes; they signify sloppiness. The white gym sneaker should be avoided, too. Are you a sixty-year-old father of ten? No? Then avoid. Retro sneakers, like an Adidas SL 72, or the Saucony Shadow series of sneakers would work well, also look at classic Asics for a refined but casual look.

Dress to Appear Older

The manner in which you dress up influences to a great degree the way you are perceived by others. And while I would be the first to tell you that it doesn't matter what other people think I know that impressions matter. It's an inconvenient truth. If your boss perceives that your sloppy, it affects how they view your work overall, it creates a bias within them. So why purposely create the “wrong impression?”

If you happen to be wearing the same sort of clothes that you had worn to college, you really cannot blame others for treating you like a kid with no practical experience. The only way to get around this is to look a little more mature and that means getting rid of your wardrobe of T-shirts, denim shorts, cargo pants, baseball caps, sweatshirts, etc. Donate everything to a deserving charity after keeping aside just a few for exercising and doing the dirty stuff, and replace them with clothes that will attest to your maturity.

Try to wear form appropriate clothing. That is, don't buy baggy clothing—look for clothes that are form fitting. I'm not saying find all the skinny jeans and buy them, no. But things that fit well. This goes for shirts, pants, etc. Form-fitting clothes make you look more like a go-getter.

Beware Fashion Trends

Finding looks and fashions you like will lead you down a potentially expensive rabbit hole.

First, I would think about what type of style you wish to embody. For me, I'm casual but put together. I'm not a sloppy person. No holes in my jeans, my shoes are cared for, and I wear clothing with branding I believe in or use. I have three suits, ten dress shirts, five pairs of jeans, two pairs of khakis, about ten or so ties, and ten pairs of shoes (two pairs running shoes, two dress shoes that are brown and black, four casual shoes, one set of boots, one pair of sandals).

For a more definitive guide, the Art of Manliness has a great article on how to build your wardrobe and breaks it down nicely.

Ensure Your Wardrobe Has At Least One Good Suit

Irrespective of what your job profile is, keep in mind that you need to wear a suit at least once in a while. Choosing a suit is tricky, go into it after doing some research on what to do and what to look for.

Make sure that the one you pick is a classically styled single-breast two-button in navy blue or charcoal gray. You should have it tailored for a good fit but if are buying one off the rack, and then make sure that it is adjusted to your size. Ask the store if they provide such a service but usually, you will need to visit a tailor. There are also many job profiles that require you to wear suits very frequently; this calls for you to choose the fabrics and colors with a great deal of care so that you are never out of place anywhere.


When going out in the real world for the first time, in a professional capacity, it's important to reflect on the clothes you wear. How long have you been wearing them? Life has seasons, just like fashion, things come and go into and out of fashion all the time. Does your current wardrobe reflect who you are today, or who you were yesterday?

Photo Cred: Chad Madden

Author Profile

Alex is the founder and managing editor at the Urban Dater. Alex also runs: DigiSavvy, for which he is the co-founder and Principal. Alex has a lot on his mind. Will he ever get it right? If he does, he'll be sure to write.

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