Startup Style for the Post-Hoodie Revolution

You’ve seen the movies and shows where young entrepreneurs, adorned in hoodies, sandals, and jeans, built an idea into a fortune. But, that’s not you. Maybe you come from a different time, a different culture, and/or you simply wouldn’t be caught dead in that outfit while in your office. At the same time, however, you’re not looking to don a suit every day. So, how do you meet in the middle and set a dress code for yourself, and, by example, for your company?

Comfort is essential, but that doesn’t mean you need to sacrifice style and any semblance of professionalism. Perhaps more importantly, you won’t need to break the bank in order to accomplish this goal of having a truly business casual look.

Dressing Right in the Startup World

As an entrepreneur, you need to be dressed in a manner that is acceptable in any situation. You may run into someone on your commute, you may have a last-minute in-person meeting, or you may simply have to go to a networking or social event after work. But, let’s get specific with some suggestions for men and women entrepreneurs in the startup world.

Here are some pro fashion tips for entrepreneurial men:

A nice sweater will be your saving grace as an entrepreneur. Have an old button-down shirt that may be a little wrinkled or has a small, unsightly stain? Throw a sweater over it. Sweaters come off as classy, but aren’t overbearing. Also, for most climates, they serve as a nice in-between – if it’s warm outside and cold in your office, or the opposite, a sweater won’t get you too hot or too cold.

Sweaters aren’t overly expensive, and there are a number of clothing establishments that sell cheap yet fashionable versions. You don’t need to be wearing cashmere when you’re working! Another tip: keep a sweater or two handy in the office. If you need to class up an outfit, or simply get cold, you’ll have a couple of stylish options on hand.

The same type of preparedness can be said for a blazer or a tie, as you should have these essentials in your office or car. Blazers can be worn in conjunction with slacks to dress up or paired with jeans (get some nice, dark pairs of jeans to round out your wardrobe) and sneakers to present a more casual look. You never know when you’ll need to run to a classy networking event or meet with a potential big-money client.

When it comes to day-to-day attire, you should have three to four really classy shirts – the same can be said for pants. Make sure you aren’t wearing baggy clothing; loose-fitting shirts and pants are the style of yesteryear. Coordinate some outfits that truly pop, and take some chances! Venture over to that high-end establishment you’ve always walked by and grab that expensive, Italian-designed shirt that may seem a little too colorful.

Also, think about the little things. Classy footwear can really make an outfit. Keep a couple pairs of nice shoes in the office or startup space – that way you won’t have to commute in expensive or uncomfortable shoes, but they will be available if required. You don’t need to wear penny loafers around all day as an entrepreneur, but if you’ve got an in-person, throw on the nice shoes for an hour or two. Make sure to have a pair of brown shoes and black shoes, and always match your belt color to that of your footwear.

And here are some pro fashion tips for entrepreneurial women:

Step one is to avoid the black on black outfits. These outfits are stylish, but black on black outfits are boring and expected, so take more of a chance when dressing for work! It’s not the corporate world, so you can adorn some colors that you wouldn’t normally wear to the office.

Your clothing choice needs to embody the soul of the entrepreneur: you need to be stylish yet assertive, confident yet not over the top. You want to own the space in which you operate and establish a presence. Try wearing that top that you save for date night every once in a while or a sleek ensemble if there’s a big meeting.

Climate is a huge determinant for women in the fashion world, so your outfit is going to vary based on the weather. During summer months, think of what to wear like you need to dress for a party where you may meet new people. Wear something appropriate (emphasis on this), comfortable, and stylish. Have some fun, but don’t go overboard.

You want your employees to see that they can loosen up a bit when it’s hot and at times when it’s difficult to wear extensive clothing. But, you also want people to keep in mind that they are at an office and work needs to be done.

You set the tone for the whole office, so be comfortable without being lazy: think loose slacks and a summery blouse. Sandals are also appropriate if they are classy enough for the office. As a general rule of thumb for fashion: if it seems like a casual article of clothing, make sure it’s a brand or style that is nice enough to compensate for that casual look. Flip-flops that you wear to the beach aren’t okay; flip-flops that you would wear to a boat cruise are fine!

Winter is a completely different monster. Buy short, chunky sweaters. A shorter, chunky sweater paired with a long thin top underneath allows for warmth while still covering up a lot. Make sure the top is the same color as the sweater. This monochromatic technique of matching the color of your top to your sweater makes a difference. It’s easier on the eyes, looks purposeful, and is more slimming.

Chunky sweaters work best with thick, narrow pants and a pair of tall boots. Make sure they are thick pants and not leggings. Buy several pairs of thick-knit narrow pants. Narrow-knit pants are key because you’ll need to tuck them into your tall boots. Adding a pair of patterned pants to dark winter outfits livens things up. For example, wear a black sweater, patterned pants (checkered or Tartan patterns are best if you can find them), and a pair of tall black boots and voila! Not a black on black outfit.

Look for kitten-heeled, tall boots. Having that 2” heel adds just the right amount of feminine style while avoiding the pain of walking in high-heeled boots. Also, try to match your boots with the color of your pants.

If you stick with my monochromatic techniques, coats are simply icing on the cake. Any color on top will work when the foundation matches. Just do yourself a favor: stay away from the rectangular bubble type of coats unless you can cinch the waistline with a belt.

Adapt to the Situation

As a leader, you don’t need to be the BEST-dressed person in the office, but you should always be professional. It’s hard for people of any age to respect someone who wears sandals or t-shirts into the office. You may also want to advise your employees to do the same, and you can accomplish this without seeming too “corporate.” Simply mention that they should wear something a little more professional “in case a client or customer were to come in.”

If you know that you have a meeting, dress up a little more than usual that day. This will show your employees that something important is happening, and they will likely adjust their mood and demeanor to mirror your adjusted look. Every once in a while, throw a tie on or wear a classy blazer or dress/skirt.

Another pro tip: if you’ve been out too late at a networking event or social gathering the night before, overdress! Your employees will think you’re aiming to be super productive that day, but you’re really just overcompensating for being a little tired or hungover.

Take Some Advice

As a leader, you may feel that asking employees for advice, especially with regard to style, is a little difficult. It isn’t, and it will actually elicit a positive response! If you have a stylish employee, go ask them how they choose their outfits or where they go shopping!

“I love your blouse, where did you get that?”
“Who makes that shirt and where can I find a similar one!?”

Asking these types of questions may seem silly or beneath your role, but it serves a purpose. This approach will not only provide you with some much-needed fashion advice, but also make you seem more personable to your employees. You need to be careful about the questions – don’t embarrass anyone and keep it appropriate. But, this can really help to build some camaraderie and may even give you some ideas.

Taking advice is good, but you should also be taking some chances! The startup environment is a place where you can try out some outfits and not be overly embarrassed or pressured. If you’ve got an important networking event in a couple weeks, try out that shirt you’ve been waiting to wear a week or two before. Then, ask for real assessments! At first, people may be reluctant to give you honest takes on your outfits. But, as time progresses and people get more comfortable, everyone will begin to open up!

Fashion is one of the easiest things to talk about in an office setting – everyone wears clothes! You also don’t have to like everyone’s clothes! A little white lie here or there never hurt anyone. Telling someone their outfit looks good is a way to put a smile on someone’s face and maybe even inspire a little increased productivity.

Bob Adams is a Harvard MBA serial entrepreneur. He has started over a dozen businesses including one that he launched with $1500 and sold for $40 million. He has written 17 books and created 52 online courses for entrepreneurs. Bob also founded BusinessTown, the go-to learning platform for starting and running a business.

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