Dressing Like an Entrepreneur

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Years ago, many Entrepreneurs wore ties to the office and casual Friday’s were unheard of, unless you were speaking about meeting your work colleagues, customers or investors in the pub after the workday was done.


But now, things seem to be different. Polo’s, Chino’s, Jeans, Open Neck Shirts – the list is endless. But even though the modern day Entrepreneur needs to keep it simple and comfortable enough for the workplace and for meetings, one can still be unique and stylish, adding a personal signature to an overall look.

As an Entrepreneur, I’m a true believer in being independent and a free-thinker, so here are my top ten tips for dressing to win and impress.

Clothes should reflect a style that makes you appear successful, comfortable and confident. But don’t be afraid to develop your own style, too.



  1. First off, know your meeting attendees. What do I mean by that? Simple. Do a bit of research to know the person or group you are meeting with. If you are off to a meeting in California with a bunch of thirty-something Silicon Valley people, do not wear a suit. Chino’s, Nice Jeans (get a good pair such as Tommy Bahama) and an open neck shirt would work. (A hidden-button down collar works well). But, if you are planning to visit New York City to meet with lawyers or investors you’ll likely need a nice suit or at least a sport jacket (please – no big, loud checks or stripes, you can show off your personality somewhere else). Pair the jacket with neutral colored trousers or slacks (I use the term slacks to describe business casual pants). But check your audience first. There is nothing wrong with sending an email ahead of time and ask: “Just checking on the dress code for the meeting! Is it suits and ties or business casual?”
  2. Even though it might be out of vogue, Entrepreneurs may STILL wear a tie for business meetings both inside and outside of the office. In fact, if you are travelling overseas for meetings (which I do a lot), be sure to check local customs and business dress because in many countries businessmen and businesswomen still wear formal attire for meetings and dinners. However, a word of caution. In some countries, be careful about the color of your tie. Certain colors have different meanings. For your choice of ties, go with an expensive option. You can get away with a less expensive shirt, but not the tie. Ferragamo and Hermes ties are wickedly expensive but they will outlast cheaper options and they always look great. I’m still wearing some of these ties I purchased years ago (both tie brands are sold at airport stores, such as London’s Heathrow Airport). And these ties seem to be timeless with their styles and patterns.shutterstock_145190851
  3. When building and accessorizing an outfit, Entrepreneurs should choose between a variety of accessories, including a bold tie and classic French cuff shirt. Accessorize with a decent pen such as Mont Blanc along with a pair of cufflinks, to keep the look trendy, yet professional. Lately, I’ve been quite taken with Tateossian cufflinks although they are a bit pricey. shutterstock_203276854
  4. There are an abundance of suits and jackets to choose from, but I like the more classic look and I’m definitely not built for the ‘slim’ or ‘tailored’ look.  But nevertheless, it’s important to keep trendy and up to date with your outfit. The smaller, independent clothing stores usually have knowledgeable sales people and sometimes you can find clothing that is unique and well made. GQ Magazine provided a great summary of some of these stores around the US. Fillings, a Gentleman’s Outfitter in my hometown of Lancaster, Pennsylvania is a great example of a company that knows how to treat and customer and Jay Filling, the owner, has never steered me wrong in the 25 years or so I’ve known him.  So check Fillings out if you are ever nearby. If you are close to a major metropolitan area Nordstrom is always a good bet. My all time favorite is Brioni, but you’ll need a fat checkbook tobuy anything from that line! But again, there is no substitute for quality. I’m still wearing clothing purchased from aBrioni store many years ago. One of the things I learned years ago: do not listen to the advice of the sales clerk if you feel in the slightest bit uncomfortable with what youare being shown. You need to exude confidence in your meetings, and if you feel the suit or outfit you are wearing might not look nice, then forget it. There are some good sales guys out there, and with a bit of trial and error, you’ll soon get to find one you can trust.shutterstock_147374198
  5. Shirts are an important part of your outfit. And although there are lots of options, you’ll need a shirt that has been made by a company that understands business shirts. I’m a big fan of Charles Tyrwhitt. They have great styles and choices. You can send them your measurements and they will customize your shirts. Delivery is quick or you can visit one of the US stores . I particularly like the non-iron selections for travel. I’m not saying the Charles Tyrwhitt shirts will last forever, but at the prices they charge it’s an easy choice to replace the shirts when they look a bit beaten up. I prefer French Cuffs, but that might be an age thing. With a crisp, well made shirt, nice cufflinks and a brand name tie together with a superior quality jacket or suit, you will project the right amount of a confidence and professionalism at your business meeting.
  6. Trousers or slacks are always challenging in my opinion. There is nothing worse than a pair of trousers or slacks that are ill fitting. Again, this is where a good sales clerk or store-owner can help make sure you look your best before buying. My favorite trousers and slacks are the Italian made Zanella. They always look great and seem to last well. The Zanella brand has just been taken over by a US Investor group, so I hope the new owners don’t mess up the Company. Zanella’s can be purchased in many of the larger department stores around the country. Zanella offer many different styles and colors, they mix well with a blazer or sport coat and travel well. Check the hyperlink above for more details. If you don’t have one, invest in a trouser press. Place the slacks in the press and the heating pad quickly removes wrinkles and sharpens creases in both pant legs at once. Great for overnight use as there is nothing worse than appearing at a meeting in crumpled slacks.
  7. Whether its a casual day at the office or enjoying time with friends and family on the weekend, wearing good quality jeans and a collared shirt is a quick and simple base for a truly stylish yet classy casual look, which can easily be transformed into an elegant look by adding a blazer. This modern style can further stand out by adding a shirt with a hidden-button down collar, such as those from The Field. Collars that don’t have a tie to hold them in place have the annoying habit of curling up. I don’t particularly like traditional button down collars, although I own a few. A hidden-button down collar is good way to keep things under control. If you are considering a short-sleeved shirt, Reyn Spooner offer some great choices. These Hawaiian built shirts dating back to the 1940’s are classics. Now with modern as well as some original designs, Reyn Spooner shirts are well made, functional and with the most amazing artwork and patterns. One word of caution, these shirts are made on the smaller size, so I order one size up. Check out their swimwear, too.shutterstock_294034727
  8. Shoes are a personal matter. I prefer black shoes with clothes of blues/grays and blacks while brown/tan shoes go well with khaki/brown and neutral colors. But I’ve friends who mix it up and seem to get away with it. I guess a nice pair of dark brown shoes would go well with a dark blue suit or slacks. My all time favorite in the shoe line is….boots. For some reason, going back to my youth, I like boots. I have several pairs of all colors and kinds. Some are zippered and others are lace up. Aldo do nice boots and shoes as do Florsheim. But the best bit of advice I can give you here, regardless of whether you choose boots or shoes is to keep them clean. The worst mistake you can make is attending a meeting or function and your shoes are scuffed and dirty. It doesn’t take much to clean them, and you’ll prolong the life of your footwear in the process. The very best shoe and boot polish in existence is Kiwi. While serving in the Navy, this was my polish of choice when cleaning footwear!
  9. The weather doesn’t always cooperate, which is why raincoats, heavy winter coats and outdoor jackets were made. For rainwear, you can’t beat Burberry. And it’s a company with a very successful history of providing protective clothing to British Soldiers in WWI, Roald Amundsen and his team who become the first people to successfully traverse the Northwest Passage and a bunch of other famous people. Check out this old advertisement to see what I mean.shutterstock_212978260
  10. Finally, lets talk about travel accessories. If you are going to a meeting and you have a bunch of things to take along (laptop, brochures, notebook etc) then you’ll need a decent size briefcase/briefbag/backpack. And, if you are going overseas for the meeting then a sturdy, well-made suitcase is on your pre-flight shopping list. My all time favorite is Tumi. Tumi is a manufacturer of briefcases, suitcases and bags for travel. They are based in South Plainfield, New Jersey. Tumi products are legendary in their ability to stand up to wear and tear. I’ve owned several pieces for years and they still look great. If your budget runs to it, buy leather as I think they look nicer. But the ballistic nylon looks great, too. Each Tumi product has a 20-digit tracer code. Registering your luggage or briefcase with Tumi provides peace of mind that it will be returned to you even if your luggage tag is removed. Another great option is Tumi’s T-Pass®. Tumi has designed briefcases, bags and backpacks that are designed to meet TSA checkpoint requirements, which allow you to go through security without removing your laptop from the case. The split-opening case must be packed appropriately to ensure an unobstructed scanning of your laptop. Probably worth mentioning that the TSA reserves the right to ask anyone to remove a laptop from its case, or re-screen any laptop or case. T-Pass® works mostly in the US, as security screening processes in many International airports do not recognize the T-Pass® system.


My final word of advice is that your look really needs to be professional. People respect an organized, clean and disciplined look. You can still look good, even if you’re an entrepreneur just starting out on a shoestring budget. It’s not about having money. If you are looking at a suit from one of the men’s clothing stores  that only cost $150, go the extra mile and get it tailored. Buy an expensive tie. And always make sure your shoes are clean!


It’s the simple things that people notice, that take you far.



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