Style Tips For Male Entrepreneurs

entrepreneur style tipsIt’s possible to be productive wearing pajamas or wearing a business suit. And like Eric pointed out in his recent style post, dress clothing is optional for most entrepreneurs. But even though the freedom to dress down is part of the allure of entrepreneurship, sometimes a guy needs to clean up! Even Zuckerberg is forced to suit up on special occasions…

Like many entrepreneurs, I work from home and dress casually most days. But, sometimes I’m forced to dress up. So…over the years I’ve collected some wardrobe basics and learned a few things. Here are some style tips for men looking to upgrade their style.

The Cut

When it comes to the fit of new dress clothing, you have several different options.

Custom made. If money is no barrier, then buying custom-fitted clothing is your best bet. Find a local custom tailor to take your measurements. They can make shirts, slack, suits, or sport coats that fit you perfectly. If you want to take it to the next level, find a tailor in London or Hong Kong. If you are on a smaller budget, you can probably find a tailor in your town instead. Here in Austin we have Gassane tailors, famous for their presidential suits. Keep in mind that not all tailors do the work themselves…some outsource.

Fitted. There are companies that serve people who want well-fitting clothes, but don’t want to to shell out cash for bespoke clothing. Companies like J. Hilburn or Tom James will send a representative to your home or office to take your measurements. Then you pick the fabric and they will make pants or shirts that are customized to fit you. Not all their suits and blazers are custom made…in some cases items are pre-made and then tailored. I’ve had pretty good experiences with J. Hilburn. I’ve never used Tom James…they also have clothing options for women.

Tailored. The cheapest option is buying good quality clothing off the rack. Then, take it to your local tailor. Some bigger chains like Nordstrom Rack have in-store tailors. Of course, getting your pre-made clothing tailored isn’t the same as getting it custom made. But, it’s much cheaper and a great way to tighten up your style. Most guys can benefit from taking their existing clothes to the tailor…

Here’s a list of what every well-dressed man should own. How much you want to spend on these items is up to you. I’ve always disliked when people describe things as “investments”…but in this case the comparison is pretty apt. Good clothing won’t appreciate in value, but it is an investment in your appearance. And in the real word, appearance is important…especially for entrepreneurs who are selling themselves to existing or potential clients.


Suit. Every guy should own a suit. This is the staple of your wardrobe. Dark navy or charcoal are probably the best colors to start with. A wool suit is pretty standard, although if you live in a warm climate you might consider a lighter material or a wool blend so you don’t melt.

Sport coat or blazer. The blazer or sport coat is another important piece. Ideally, you want one that you can dress up with slacks and dress shoes. At the same time, you should be able to dress it down with jeans and Converse, depending on the occasion. Since I live in a hot climate, my navy sport coat is a lighter wool blend.

Pocket square. This is a fairly inexpensive, but important, accessory. Many times you will see a matching pocket square – tie combo. Never match the two…they should complement each other but never match. Many pocket squares are silk…but the best ones are linen. I prefer a simple white linen pocket square since it matches with most anything.

Tie. A tie is an important and obvious addition to any mans wardrobe. Ideally your tie should be silk…a Brioni or Charvet tie are pretty good to start off with. You can find them for decent prices on Ebay.

Belt. At some point you will likely need both a black and a brown dress belt. A high-quality belt can last you for the rest of your life. Calfskin is good, crocodilian or lizard skin belts are even better.

Dress shoes. After a suit or sport coat, shoes are probably the most expensive part of a man’s wardrobe. It can be tough to shell out hundreds for high-quality shoes. But they are extremely important…don’t ruin your look with cheap shoes. And expensive shoes can last a really long time if cared for properly. Your local cobbler can resole them repeatedly to extend their life.

Tie bar. A tie bar is a great way to bring it all together. Buy a real silver or platinum model and you’ve actually made a real investment!

Cuff links. Cuff links aren’t necessary. But they are rare and can really help polish off your look. You can get a cheap pair or go with silver or platinum again to match your tie bar.

Shades. Of course sunglasses are not necessary. But I live in Texas, so they are a nice accessory to have.

Bag. Some people call it a man purse. But most businessmen can benefit from owning a good, leather messenger bag. Great for traveling or carrying around a laptop or tablet.

Watch & Jewelry. I like to wear a nice watch on occasion, but for most guys that’s also optional. Unless it’s your wedding ring.

Here’s one final tip for guys…ask the women in your life to help you out if you’re stuck! Lot’s of guys have a problem finding clothes that compliment them. And picking the correct colors can be a real challenge. Some of us (like me) are legitimately color-blind…others just suck at picking colors that look good on us. Even the best cut clothes will look silly in the wrong color. Women are usually great at matching color…so ask your wife, sister, mom, or girlfriend to help pick color combinations for you.

Of course…none of these fancy clothing items is necessary. We can all get along just fine in jeans and t-shirts. But when entrepreneurs need to dress like grown-ups, it’s good to have these wardrobe essentials on hand.

What other style tips do you have for male entrepreneurs?

About Carson Derrow

My name is Carson Derrow I'm an entrepreneur, professional blogger, and marketer from Arkansas. I've been writing for startups and small businesses since 2012. I share the latest business news, tools, resources, and marketing tips to help startups and small businesses to grow their business.


  1. This level of dress is completely unnecessary for the tech types, too. 🙂

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