What to Wear?

Clothing hanging on coat rack with hat.

Clothing makes a bold statement. It offers the world a distinct impression of who and what we are. Just look at the photos from the 2019 Met Gala — the “Camp” theme interpreted in myriad crazy ways by the celebrities in attendance. Not that I’ve ever attended the Met Gala (I’m sure my invite got lost in the mail), but it’s a great example of the power of a costume to showcase a person’s personality and identity.

Back in my teenage years, I didn’t quite fit in with the crowd. I chose to express myself differently than my peers from both a fashion and attitudinal perspective. Clothes were one way I stood apart.

I distinctly recall one day in the high school cafeteria when the lunch lady tried to charge me the teacher price for my soggy chicken patty and mashed potatoes. (Just an aside, weren’t those potatoes good?) When I acted surprised and informed her that I was merely a student, she looked me up and down and said, “Could’ve fooled me!”

It’s easy to understand what confused the lady at the cash register. My outfit that day included oxford shoes, cable tights, a belted shirt dress, and my long hair up in a bun. I looked exactly like a teacher! Most of my friends during that era were wearing Jordache jeans and tight v-neck sweaters with lots of blue frosted eye shadow. Not me. They often called me the Ivory girl because I wore very little to no makeup and catered to a preppier style. In the lexicon of early 80’s Charlie’s Angels, I was definitely not Farrah.

I have a friend who collects high top basketball sneakers. He covets them, treats them like pieces of art, and displays them in all their colorful glory in his apartment, posting selected kicks on his personal Instagram. Another friend of mine has a great hat collection. She always seems to know the right topper to wear for a particular occasion. These are wonderful individual expressions of style, and if you knew each of these people like I do, you’d say their shoes and hats suit them perfectly!

Office environments place external demands on our personal clothing preferences. In my employee days, when I worked in the media departments at different agencies around New England, I could immediately sense if I’d fit into a workplace dress code, or not. Often, I would err on the side of being a little more formal than my peers, the goal being to have my professionalism evident in my clothes as well as my demeanor. It was never anything too overt – no high heels or power suits — just my own small attempt to remain true to my self-image.

What we choose to wear at home and while we are out and about on weekends is up to us entirely. I’ve been known to dash into the grocery store in a baseball hat and old sweatshirt on more than one occasion. Those are usually the times when I’ll inevitably run into an old friend or a neighbor — just when I’d hoped to remain incognito!

Since moving my company up to Portsmouth, New Hampshire last summer I’ve noticed an unexpected evolution in how people dress for work. The Portsmouth area has an entirely dressed-down vibe, unlike Boston or even the Boston suburbs where business or business casual rules still apply. You see it immediately on the streets, in the coffee shops and restaurants, and in most of the small to medium-sized advertising and design shops where we spend a good deal of our time.

One of the most obvious fashion characteristics I see at the office and around this harborside town is that jeans and sneakers are an everyday staple. Dressing up for a client meeting or new business pitch means wearing a nicer pair of jeans and (for us women, anyway) perhaps a pair of flats or sandals, maybe adding a blouse or jacket. My earlier habit of sporting dresses or skirts every day has quickly evolved into this type of lighter fare, and I’ll admit that I’m kind of like it! Of course, I still have my go-to outfits for the occasional meeting or presentation, but on a regular basis, I’ve started to enjoy dressing down a bit.

Why do I find myself willing to give up on more traditional attire later in my career? Wouldn’t you think I’d be more set in my ways than ever before? Perhaps not. I think the answer lies inside the woman I am today: the business owner, leader, teacher, mom of grown-up kids, and all-in-all much wiser version of my younger self. Today I’m more confident in my abilities and my professionalism than at any other point in my life. I no longer need to wear certain clothes to help me tell my story. This realization frees me up to experiment with my personal style, wearing jeans when I want to and dressing up my outfits a bit when I feel the time is right.

When it comes to my employees and our internal company culture, all I ask is that they show self-respect and respect for our firm in the clothing they choose to wear. If I had to put a label on our company dress code, it would say, “clean, comfortable, classy, and creative.” I believe that the unique personalities of the people on our team bring so much to the mix and I certainly don’t want to stifle that by limiting everyone to a strict business uniform.

So the journey continues — through business and life — with our unique choices of self-expression, creative interests, personal pursuits, and ultimately what we pull out of our closets in the morning as we prepare for each workday. Clothing may be what people see first, but it doesn’t define who we are. I’ve penciled in next year’s Met Gala just in case — better watch out Lady Gaga! — but for now, I’m going to continue to wear what fits, what’s comfortable and what makes me feel good inside and out.

Anne Richardson

Anne Richardson is the owner and media director of Richardson Media Group, an agency specializing in media planning and buying, advertising campaign management, and SEO.


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Anne outside the door of the Richardson Media Group office.

In addition to her role as owner and media director here at RMG, Anne authors the majority of our blog posts and hosts our BSuite podcast. Favorite topics for both platforms include the entrepreneurial journey, sustainability + social responsibility, media planning, media buying, and forming productive agency partnerships.