First, let’s put it out on the table and get this out of the way: style is not frivolous. Style is not something that should be undervalued. Style helps convey who you are and it is an incredibly powerful professional tool. Think about it: if you’re in a restaurant and another diner experiences a medical emergency, who would you approach first for help: someone wearing medical scrubs or someone in a suit? While both of these people may be qualified doctors who can help, most of us would immediately gravitate toward the person wearing scrubs in this situation. What he has worn signals a profession that can help with the situation at hand, even if the person in scrubs is say, a vet, and the person in the suit is, in fact, a doctor. While scrubs may not someone’s first style choice, this example illustrates how what we wear can powerfully indicate who we are. How can over or under dressing impact your career?
We’ve heard it a million times before: dress for the job you want. But what does that really mean in today’s workplace where professional environments are more and more casual, tech CEOs wear hoodies to give world-wide presentations, and employers and potential employers can easily get a glimpse into most lives with a quick online search?
In some ways, the “rules” are the same. If your company, office, or industry has a dress code, stick with it. Dress as if you’ll run into the company’s top decision maker at any given time. Even if your office or industry has strict professional dress codes, there are ways to add personality to most any work outfit. Overall, I think of things in thirds. As a wardrobe consultant and personal stylist, for client meetings I usually employ an outfit with 2/3 fun and whimsy to 1/3 structure. For example, I might wear a skirt in a conservative length with a bold but neutral pattern and a striped cotton t-shirt for the top with flat mules in a fun color. In this case, the cut of the skirt gives structure while mixed patterns and a bold shoe color add fun. If you work in a creative role or industry, this formula will likely work well for you, too.
If you’re in a very structured industry, such as law or finance, no matter where you fall on the org chart, dress in traditional professional outfits: well-tailored suits, blouses or button ups, etc. Where you can pull your power play will center more around color and cut than anything else. Go for the classic black pencil skirt but pair it with a loose blouse tucked in (professional but relaxed) and knock ‘em dead heels or flats in a bold color, such as red. When a person walks into a room with a distinctive accessory, attention is immediately on her — use it to your advantage to command the room. For the gents out there, a tie in a bold color or a patterned pocket square will make you distinctive yet authoritative. These types of professional dress codes really require a formula of 2/3 structure to 1/3 whimsy, or even less. If that’s the case for your work place, look for details, details, details. That black suit jacket with subtle ruffles around the peplum waist, a pencil skirt with flattering seams that draw the eye up, or a suit in a graphite rather than a flat black offer thoughtful details. Regardless of the formula that best adheres to your required dress code, these examples all add distinction, which conveys confidence and gives you an edge over your peers.
If you work in a more casual setting, think about your every day tasks. Are you running between departments on a regular basis (hello, flats!) or are you more stationary? If you’re the bottom of the totem pole, so to speak, I recommend over dressing just a tad…it can be as simple as dark jeans with a flattering blouse and pointed-toe flats compared to your counterparts’ jeans, t-shirt and sneaker uniform. If you are in the middle of the org chart management-wise, you can change it up a bit differently: think about trousers (with a stretch material for comfort) paired with a simple sweater in high quality fabric, such as cashmere or silk blend, and bold-patterned sneakers or flats.
When it comes to style, I’m all about function first. If you teach preschool, you may regularly be in comfortable stretch jeans and an easily washable cotton shirt; if you’re looking to be promoted to an assistant director position or know you will be interacting with parents constantly, consider wearing ankle-length trousers with stretch in them and an equally comfortable (and easy-to-clean) blouse in a fabric that is easy to move in. Dress it down with fashionable sneakers and a front tuck of the shirt. You have a very practical outfit for being on the floor with kiddos and helping them with art projects but still command an authoritative respect from both the kids and other adults you interact with.
I have covered a lot of over dressing…can you tell I veer that direction? Likely because, aside from a brief flirtation with tracksuits in the early 2000s, I’ve pretty much been overdressing since I was able to dress myself. Stylistically speaking, it’s a comfortable space for me though I realize it may not be for you. If this is you, fear not — there are ways to approach over dressing while still feeling like yourself. Look carefully at fabrics. There are flattering trousers out there in comfortable fabrics. Look for ones that are cut well in a fabric that is comfortable for you with a bit of stretch, and invest in the best quality you can for your budget. These won’t feel like overly structured pants but will hold their shape throughout the day while feeling like jeans you’re already comfortable with. There are a ton of soft rayons, modals and silk top options from many different retailers that add some texture and are incredibly comfortable to get you through a work day. If button-up tops are a tough fit for you, try a blouse with a v-neck or split neck line and tuck it it. It will create a lovely balance of structure and flow.
So how can under dressing be powerful?
Frankly, you need to be up a few rungs on the ladder to get away with under dressing. The intern wearing flip flops is less likely to get invited back for an entry-level job compared to a peer who came to work each day in a more structured outfit. Whether this is fair is a debate for another time. But, for those a couple of steps up on the org chart, adding some casual aspects to your outfit, especially if you work in a creative field or department, conveys creativity to your superiors (how novel that Jane wore a fitted sweatshirt with tailored pants and heels today!). Looking just a little different commands attention and gives you the floor…use it as an opportunity to say what you want to say. Additionally, it’s a great way to make direct reports feel comfortable since it makes you more relatable, likely making your reports feel more relaxed in your presence to openly communicate.
I remember seeing an interview with Rachel Ray about how she launched her magazine. Apparently several publishers had approached her previously and she wasn’t interested, then Oprah called. And, in Rachel’s words, “you don’t say no to Oprah.” So a meeting was set and Rachel spent a substantial amount of time stressing about what to wear (as I think most people would) to meet Oprah who is going to pretty much tell you “you need to do this magazine and my company wants to publish it.” Rachel settles on her outfit, goes out to meet Oprah, walks in and sees Oprah is in a simple white shirt and jeans. Rachel immediately relaxes and feels overdressed and silly for stressing about what to wear to the meeting. Now, I think the majority of us would have been Rachel in this situation and I don’t think that Oprah under dressed as a way of trying to exert any sort of power over Rachel but it illustrates the power that under dressing can have. My suspicion is that Oprah wore a casual but elegant outfit to make Rachel feel more comfortable in this situation. We also see underdressing pretty regularly with tech CEO’s at large events such as new product launches. This isn’t by accident. While there are a lot of cowboys coming out Silicon Valley wearing eff-you flip flops, many likely also want to feel approachable by the average potential customer.
Whether you employ over or under dressing as your power play, you still need to be cognizant of your work environment. If a shirt requires a strapless bra, that’s an automatic no; a bit of shine from a textured top is fine; sequins on any portion of your outfit would just be too much. We spend a huge percentage of our time working, we need to invest in clothes that can keep up with us and take us to our next professional goal.