Dress for Success: It’s Not Just A Suit

So…every Monday is “Dress for Success” for our business program. It’s a great opportunity for kids to dress—and hopefully act—more professional and responsible. I love Dress for Success, and use it not only as a teaching tool, but to evaluate anything that might be going on in a kid’s world that requires my assistance. We maintain a closet for kids who forget (or just don’t have) their dress clothes, which kids can access freely anytime during the week. 

So…this Monday is also Spirit Day at our school. Monday’s theme is “Chill out”, with kids encouraged to come to school in their pajamas.

What to do? What to do? What to do?

It’s really quite easy to me, and completely depends on your definition of “Success”. 

Do you define Dress for Success as looking like a cookie-cutter, suit-wearing clone on Wall Street? I don’t. Certainly not in the corporate environment our students are entering. We need to prepare them for all eventualities—not just the Hollywood version of a successful “businessman”. 

Dress for Success in my classroom includes supporting the corporate culture and traditions of the environment you are working in. For my school, for Monday, the culture of our school will be “chilled out”. Supporting that Student Council initiative, in my professional opinion, is an excellent example of the non-conformist Dress for Success model for this generation. 

So…jammies and slippers will get full credit, too. 

The Five C’s To Dressing For The Right Occasion At The Right Time

I’ve regurgitated the quotes for years, just like you: “Dress like your boss’s boss” and “Dress for the job you want, not the job you have”. But the current corporate environment doesn’t support the traditional thinking on the subject. With Silicon Valley leading the charge for “Casual Everyday” instead of just Friday, many of the hottest professions we are training these students for do not wear suits every day. 

We need to grow with the times, and support our students’ being successful in environments that might be quite foreign to us. 

We need a new model for Dress for Success. Introducing my Five C’s:

C – coordinate

I absolutely, positively do not care what job you are trying to get, you must wear a matching, well-coordinated outfit. What that means can vary wildly across different industries, but seriously, Boo Boo, you need to look good. Your definition of good doesn’t have to match mine, but it should follow some type of standard. While a polo and khakis might be suitable for a Target interview compared to a full suit for a para-professional position in a law office, neither will get you the job if they are not well-coordinated and look presentable. 

Well before the interview day, encourage students to try on their chosen outfit and spend time in front of the mirror from a critical perspective. That is the time to find out there is a stain on the tie/scarf, or a missing button on the shirt. Ill-fitting pants can be replaced a week in advance, but not the day of. In my experience, shoes are quite a downfall for our young professionals. Encourage them to buy a single pair of black dress shoes—kitten heels at most for the young women—so that they will have something suitable no matter what they wear. 

C – choose quality

There isn’t a teen on earth who is interviewing with a Rolex on their arm. That’s not the type of quality I am referring to. I’m not brand conscious when it comes to interview attire at all. I am, however, a quality snob for the outfit. Even if you are going to an interview in joggers and a tech t-shirt (think applying at the local gym), you need to make sure that the outfit you choose is relatively bright—not faded, well-fitting and appropriate for the environment. 

I’m absolutely not above wearing clothes from a big-box store—I’m looking at your CostCo!—but strongly encourage my cash-strapped teenagers to visit local thrift shops to build their professional wardrobes. It is quite possible, and significantly less expensive, to find excellent quality, barely used merchandise in a second-hand shop that you can use to obtain interview clothes. Thrift shopping is how we maintain our clothes closet in my classroom. There has never been a visit to a second-hand shop that hasn’t netted me at least a few ties and suit jackets for both genders—they are a goldmine.  

C – consider the career

I love Hot Topic. Really, I do. I can’t stand their merchandise, and going in there makes me break out in hives, but they have a spectacular business model that I reference in class several times. Hot Topic is the perfect metaphor for dressing for the chosen career. Every employee they have is, quite obviously, a fan of their merchandise. So applying there for a job, leave the Brooks Brothers suit and the Kate Spade purse at home. 

I am a firm believer that college isn’t for everyone, and the trades are too often overlooked as career options for our youth (getting off soapbox and saving it for another blog!), and I use those careers in my discussion about dressing for an interview. You wouldn’t wear a suit to a job as a day laborer. But you wouldn’t wear torn pants, either. It’s important that we teach our students to prepare for the career they are pursuing, and not fall into that erroneous belief that Dress for Success only means a suit. 

C – confidence

We’ve reached the most important part of Dressing for Success—what you have within you that you let shine through. You need confidence. Self-confidence in not only your abilities, but in how you present yourself. This is, really, why we do Dress for Success—to get students comfortable in that “costume”, so when they go for that college interview or that job, they are wearing something that is familiar and feels comfortable on them. Being comfortable in your outfit will help you maintain your confidence in your abilities to succeed well past the interview stage. 

Building this confidence comes in many forms, and should be reinforced on a regular basis. Not only is it important for them to be comfortable in their interview clothes, but they also need practice and assistance with the confidence that comes from repetition of interview techniques. While they are “dressed up”, this is the perfect time to do a quick ten-minute handshaking warm-up, or maybe throw them an interview question as their exit ticket. Help them maintain their confidence when answering your questions—have them look you straight in the eye, and review with them how much better a slight smile looks to the interviewer. 

Help them lose the “deer in the headlights” look teenagers often have. 

C – charisma

RobberBaron has tremendous charisma. His ability to make others comfortable in his presence, and inspire them to agree with whatever he is telling them is absolutely uncanny. 

He is the perfect salesman.

Which is exactly what a person needs to get that job. 

In my decades of experience, all students behave differently when they are Dressed for Success. They stand a little taller, walk with purpose, make better eye contact, and have a much more pleasant demeanor. It is extremely rare for someone to skulk into my classroom on a Monday with their head down and a sour expression. Something about dressing in their best leads them to act like an adult with a purpose. An adult with a job. 

That is what makes Monday so important. I need to work hard to harness these positive, outgoing thoughts so that they become more familiar and normal for students. The sooner they can develop a positive attitude about their appearance and abilities, the sooner they will find that inner charisma that will draw people—even potential employers—into their spell. 

So, I give more compliments on Monday. I stand at my door an extra minute or two having brief conversations. I walk the room more frequently, commenting positively on every students’ efforts to look professional. I shake hands instead of just saying hello. 

Most Importantly

Students need to be true to themselves. They go through much of their life trying to please someone. They have “bosses” at home and more of them at school in the front of the classroom. They answer to their coaches, their Advisers, and the employers. They need to have their own voice in what they are wearing to support their confidence.

So, yes, that SpongeBob tie is acceptable. Yeah, I know that skirt is barely meeting dress code, but it’s acceptable for Dress for Success. Ok, I know you love those heels, but you can barely walk, but it’s fine for today. 

I help them feel strong and powerful, until they gain the confidence to feel that way on their own. Sometime in April, usually, of their senior year.

But for Monday…jammies are fine!

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