Dressing for Success in a Start-Up: When and How to Ditch the Hoodie

Business.com / Starting a Business / Last Modified: February 22, 2017

Here are some simple suggestions and tips to help you knock it out of the park by dressing perfect for every business situation.

So you just graduated college and your buddy has a killer idea for creating a brand new platform to shake up an entire industry.

He wants to meet you for coffee to pitch you on the concept and he wants to get you to be part of his startup team. So, after the excitement starts to wear off (just a little bit), it hits you. What should I wear to the meeting?  

Dressing for success comes with a lot of qualifiers. What does success look like? How should you dress for different business situations? Don’t worry.

Here are some simple suggestions and tip to help you knock it out of the park by dressing perfect for every business situation, based on my personal experiences in the world of startups and Fortune 500 consulting. 

Related Article: Dress to Impress: Work Wardrobe Staples Every Professional Woman Needs

Know the Person You’re Meeting With 

When I was starting out as a freelancer, I enjoyed the extreme casual dress code that came with finding clients online. There were days where I legitimately didn’t change out of my pajamas until I took a shower at the end of the day. Hey, if your commute is a matter of rolling out of bed and into the office chair three feet away, why bother with changing?  

But, as I grew I started to build relationships with clients around town. What I realized was that meeting people in the community and earning their business was pretty profitable. And with all the newfound person to person interaction, I needed to start putting more thought into my wardrobe. 

I like to look at a wardrobe as just another way to do what psychologist call “mirroring”. To build instant rapport and a sense of comfort with other people, just do what they do. If they fold their arms, you fold your arms. If they show up to work in shorts and a t-shirt, you show up to work in your favorite t-shirt and shorts. If they wear cuff links, then go to the store and get a high-end outfit to match their style. 

To effectively mirror someone else, you need to know them so that you can prepare ahead of time. If you don’t know them well, or have never met before, go with business casual for a solid, middle of the road approach that hedges your bets in either direction. 

Think About the Purpose of Your Meetings Throughout the Day

Even if you work in a super casual environment, you need to give some serious thought to what your schedule looks like for the day. For example, if you have a meeting with a new client, then it’s a great idea to dress to impress. Make an amazing impression, and if you find out they’re laid back and casual, you can always more effectively mirror them after you’ve won the account. 

Related Article: The C-Suite Responds: Are Piercings & Tattoos in the Workplace Still Taboo?

Dressing up is a sign of respect, and new clients love to feel that they have your full attention and effect. The level of detail in dressing yourself is a subconscious communicator of how detail oriented you are. 

Tips From My Girlfriend

All right, for this part of the conversation, I’m going to have to rely on the input I received from my girlfriend, Michelle. She’s managed to climb the corporate ladder pretty effectively, so I’m confident that she knows what she’s talking about. 

Comfort First 

Don’t wear uncomfortable outfits. Whether it’s a pair of heels that kill your feet, or a dress that’s gotten uncomfortably tight in a few places, if you’re uncomfortable at work it will impact your performance throughout the day. Plus, if your shoes are uncomfortable and you take them off in your cubicle, there are some unsetting side-effects that are sure to make you the least popular person in your department. 

Say Yes to the Dress

Spring has sprung and you’ve got some killer dresses lined up in your closet. Michelle says, “Say yes to the dress.” Just make sure it’s workplace appropriate. That means the length needs to come down to somewhere between your knees and the end your fingers with your arms at your side. The design of the dress is also important here. In terms of neckline, high necks are perfect for more formal environments.

A V-neck might be something you’ll want to spend some additional time considering; too much cleavage can signal that you aren’t a serious professional and give off the wrong message to coworkers in an office setting. 

If, like Michelle, you’ve got a killer body that you want to show off, don’t be afraid to go with outfits that are a little more form-fitting. Trade a little curve for cleavage and you’ll find that you’re still able to turn heads without offending sensibilities. 

Related Article: Interview Success Secrets: How to Project Confidence With the Right Attire

Overall, I hope that you’ve learned a little from my and Michelle’s experiences dressing to impress for any occasion. With a little thought and planning you can kill it in any situation with the perfect outfit that exudes confidence, comfort and professional style.

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