So if you are getting out of college, graduate school or even high school and starting to work in a professional setting, it is important to maintain a good impression with your bosses and your upper level managers.. This is especially important if like me, you had a baby face, or in general you are just young. Regardless of what anyone has told you, you don’t know what you don’t know, you may or may not know how to deal with the politics of working in a company.

I wish it was not the case that we are judged, but get used to the fact you will be judged every day of your career. You will be judged on how you handle meetings, how you handle conflict and yes, even how you dress.

I found changing my wardrobe made a noticeable effect on how I was perceived. This included my peers, my senior management and even led to presentations in front of the C suite at several Fortune 500 companies. When you are presenting to the CEO, CFO, General Counsel or other C suite executives, Jeans and T-shirt are just not appropriate, regardless of what kind of company you work at.

Many of you are going to say something like, “hey my company, we don’t wear suits, everyone wears what ever and is super chill”. And I am going to say in that case, these rules apply even more. This ultimately is not to impress your peers, but to make a lasting positive impression of the senior leaders in your company. I applied this rule for myself at Financial Companies as well as super casual tech companies on the west coast.

Rule 1: Khakis are no longer allowed

Just about every guy I know defaults to khakis when they work in a business casual environment. Nope, no longer. If you are in a situation where you’re casual enough for khakis, its casual enough for jeans then. A nice pair of dark colored denim is also more stylish than khakis. Instead, you are going to switch you trousers. You can do a lightweight wool, but I even used polyester (gasp) trousers from Kenneth Cole that were more comfortable than khakis and looked much better.

The problem with khakis is they are no dressier than jeans, but less dressy than trousers. They fit in this odd ground in between the two. Your rule of thumb is always to dress one or more levels better than those around you. The only con is your dry cleaning bill might go up a bit.

Kenneth Cole REACTION Men's Twill Stretch Modern Fit Flat Front Pant, Black, 36x32

Rule 2: if it looks good with a tie, it looks good without a tie

This is something you will have to get your head around. Because when done right, a shirt you wear with a tie, can easily be worn without a tie and still look slick and professional. So in my case, I would look for shirts with an english spread collar which laid real nice along your shoulders and neck without a tie. I also would wear french cuffs sometimes which gives you a layer above those around you.

There will be times when it is appropriate to wear a short sleeve shirt. Going for a golf shirt will work, but I found a couple brands of button up short sleeves I like. In all cases the collar laid nice, had a flat bottom to wear un-tucked. This worked especially well in the middle of July when it was just too unbearable to wear a long sleeve shirt.

Michael Michael Kors Mens Regular Fit Glen Plaid Dress Shirt 17 1/2 34-35

Notice the Spread Collar? Good with or without a tie.


Rule 3: Sneakers are out

Even if you are wearing jeans, sneakers are out. Unless you are going for hipster douche bag look, its time to put on big boy shoes. This means for lack of a better term, dress shoes. You can do suede if you want, but I always stuck with black leather. This way I didn’t need to have multiple belts and I could wear them with just about any thing. My favorite was a pair of split toes shoes. While not as dressy as a Cap toe I felt like I could easily wear them with jeans as well as a suit.

Allen Edmonds Men's Ashton Split Toe Oxford,Black,10 B


Rule 4: Cover your tattoos

This will be controversial because people with tattoos love their tattoos. But the rule of thumb, is in a corporate environment, you keep them covered. So if you have a full sleeve, you will wear long sleeves. You want the boss to concentrate on your achievements, not your skin art.

Starter Wardrobe

If I was to go back into the corporate world or graduating from college and didn’t have to wear a suit, I would start with the following. 2 – 3 pairs of black and/or charcoal trousers. Either light weight wool or polyester. Don’t worry about wool, as it breathes really well and will be more comfortable than cotton over time. The great thing is, as a man, no one really notices your trousers, and if you had a suit, you would be wearing most of the same things all the time. I would then add in a dark blue denim to wear as well. If dry cleaning is needed, you can rotate through your trousers.

Second would be 5 – 8 button down shirts. There are lots of plaids with a subtle pattern you can get. I would mix normal cuffs with french cuffs. Over time you can add to this. But it gives you enough variety over time to not have the same clothes on all the time.

For undergarments we are talking about t-shirts, socks and underwear. I am not going to tell you what underwear to buy ( I like Ex_Officio) but for undershirts, Calvin Klein makes these awesome shirts with a lot of lycra in them. If you drank to much beer in college, this comfortably holds in that fat to make your shirts lay flatter. They are also thin so they are not over tho during the summer.

Socks are up to you. You can go colorful or go plain, but you will need dress socks. I find it amazing the quality of socks these days. I have been wearing this one companies dress socks that have a wool exterior and silk interior for super comfort. If you buy too thin a sock, your dress shoes will slip.

Shoes are up to you. But a nice pair of leather uppers is the way to go. Don’t skimp here because remember, you will be in them for 10 plus hours a day. Don’t skimp. I like Allen Edmonds, Cole Haan and others for their comfort. You can go for a split toe, cap toe or detailed oxford. Buy the right shoes and they will last you for years.

Completely Optional

Watches to me are more of a jewelry option than a time piece. I haven’t worn a watch in years since I can just look on my phone to see what time it is. If you are going to wear a watch, make it something special. whether you buy a high end divers watch or apple watch, it is up to you.

If you have french cuffs, you will need cufflinks. If you are low on money, than get the silk twist knot cufflinks that are easy to put in. They are more casual but work really well and you never have to worry if you lose them. But over time, you might want to buy or borrow a pair of metal cufflinks. I inherited some from my dad. Most I don’t wear but there is a pair of silver ones that I love. See if Grandpa has some from his youth.

Your Goal

Your goal is to change perception of you. Ultimately, yes, your work will define how well you have done, but I have seen some super talented employees never move up because managers didn’t want to put the guy with black shorts, t-shirt and army boots in front of the executive, no matter how good his work was.

It is not just work either. You will feel more confident all around when you are dressed nice. This is something the opposite sex will notice as well. And over all, we are looking for a more adventurous and fulfilling life.

So get your wardrobe in order, and move your career ahead. I will try and talk about suits later in time but to be honest, I have not worn a suit in 20 years except for interviews. I am not sure how much it applies but if you work in some industries it will.