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Dressing for Success: The Dos and Donts


Guest-writer Ashley Thompson is a freelance writer based out of Virginia, U.S. Her English degree is being put to use writing about fashion and beauty instead of Chaucer and Yates. When she’s not following her passion, she enjoys attending concerts with friends and wandering her favourite city, Richmond. Read about her ideas re dressing for success, an exclusive for Currently Loving.

Dressing for success is an art – however, one that can often be tricky to master. A professional wardrobe should impress; it should mirror the determination we feel. Equally or perhaps even more so, it should allow for a sense of individuality. As a grad student in her mid-20s, I am constantly striving to achieve an ideal balance between looking polished and put-together without sacrificing expression of my own style. I believe that there is a freedom in dressing for yourself, in finding pieces that appeal to your unique aesthetic, and in wearing what makes you feel your best. I’m sure I’m not the first to say that the right outfit can do a world of good for your confidence, mood and overall perspective. In fact, I know from personal experience how true the notion is.

While there are plenty of tips for creating a successful work wardrobe out there, it can be overwhelming to sift through the advice and even more difficult to apply these words of wisdom to your life. So, I’ve done it for you, taking on (most of) the legwork to bring you what I’ve found to be the most helpful dos and don’ts of dressing to impress. That is, without losing your own style in the process.

Do: Dress Like Yourself

We’ve all heard the adage to dress for the job you want, not the job you have. However, Marie Claire points out that this age-old mantra is just that—old. Dressing like the best version of you is a better “do” to follow; after all, that’s who your boss/manager/supervisor hired! And while “dressing for the job” is still important, the meaning of this statement has certainly taken a shift. My advice? Look to the people you respect in your industry or company for tips on dressing for your particular career or workplace. Does your boss wear polished jeans and a blazer most days? Is the co-worker who just got a promotion rocking a suede skirt and ankle booties? Consider what others are wearing and interpret these looks in a way that feels true to your own sense of style and self.


Don’t: Be Afraid to Show Off your Own Style

Whether you love playful patterns, bold colours, or feminine accents, there’s no reason why you can’t rock them at work. The biggest “don’t” when it comes to dressing for success is restricting your personal style. The truth is, looking professional doesn’t mean sticking to a script. So how do you incorporate the details you love into your career wardrobe? Choose polished pieces which feature pops of you: a blouse with a geometric design, sheath dress with embellished collar, or pencil skirt in a bold colour. These are all ideal for showing off your style in the workplace. Check out Lyst for inspiration – their collection of pencil skirts offers a valuable idea of the latest trends. The wide range of styles, designers, and silhouettes showcased will make it far easier to take in all options; to find the ideal piece for your wardrobe – better yet, your fashion aesthetic.


Do: Bend the Rules (But Don’t Break the Dress Code)

Some rules are meant to be broken: sticking to neutral-hued power suits or never mixing your prints. I’m going to encourage that you do bend the rules in more than your everyday fashion – when it comes to workplace fashion too. Heard you can’t wear those vibrant orange trousers (that you happen to be obsessed with) to the office? I say wear them. Someone told you that there’s no place for a jumpsuit at work? News flash: there absolutely is. Create ensembles that make you happy and that are a little unexpected, even if this means bending the rules a bit. The only caveat: don’t sacrifice dress code in the name of personal style. Some workplaces are stricter than others, and some are perfectly fine with having casual Friday every day of the week. Make sure you know what your office’s boundaries are so that you’re able to play around without crossing the line. As Lauren Conrad writes, sexy and revealing clothing, as well as clothing that is ripped, torn, or just plain sloppy (this includes your old concert tees and much-loved beach flip-flops) should be avoided, regardless of office dress code.

Afterword by author of Currently Loving, McKenzie Collins: 

With most of us on our way to uni, or into the workforce, Ashley’s advice has never come at a more sound time. If I could possibly add anything, it would be this. Don’t dress as the average waitress, assistant or intern, do but dress as the one who is destined to be much more. In your style, and in general, be confident. Allow your greatest assets to shine; don’t get caught in striving for another’s. Even more so, wear a smile and an open attitude: don’t forget that this is only the beginning for us. Unlike Drake, we’re yet to say (at least with prowess) that “now we’re here”. For now, let’s stay humble, work hard – and break only to read Currently Loving! As always, much love.




Ashley for Currently Loving xx

Imagery (street-style photographed across Europe), editing and afterword by McKenzie Collins

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