Skip to main content
The M Dash

Live with purpose.

How to Dress Up Without Compromising Your Personal Style

August 02, 2019 | Filed in: Your Closet

Every time I put some extra thought into my workwear, I end up regretting it. The last time I tried hard, by which I mean I dressed up and wore black pants to the office instead of denim, I saw my colleagues wearing jeans and sneakers and felt such envy that I could almost feel myself turn green.

I’m 29, but I have the who-even-cares attitude of a grandma and the personal style of a college student. It’s the only way to describe my countless t-shirts, piles of sweaters, and collection of denim that would put Ralph Lauren himself to shame. And I used to feel bad about it, since it seems like the sartorial version of a failure to launch. But is that so terrible? I’m just more comfortable this way. And it’s the only way I feel like I’m wearing the clothes, versus the clothes wearing me.

One big factor here is that I’ve always worked in an industry that encourages creativity. There were no business suits to be found at the magazines I wrote for, and beyond working at Vogue, a job for which I already knew my sense of style was deeply underqualified, no one seemed to mind my extremely loose interpretation of cool-creative.

Want more M.M.? Sign up for our newsletter.

Still, I’ve now managed to find a sweet spot between casual and competent. While I’m a big fan of Casual Me—I, for one, think she looks great—I also want to avoid feeling deep shame when I bump into my old Vogue editor or another industry peer I’d like to impress. (I’ve run into my former editor before while wearing my Saturday best, and it’s never not made me want to hide behind a potted plant.) In refining my personal style, I’ve found that I can show that I want to be taken seriously while expressing my passion for a more relaxed vibe. It all comes down to a few simple tricks.

Bring on the Basics

The Ronda top and the Foster pant.

Leave the negative connotations of “basic” to the children. Basic at its best just means “classic,” and you can’t go wrong with it. First, nothing can take the place of a workhorse like a slim-fit black pant. The Hockley pant plays well with everything, full stop. Meanwhile, a basic tank like the Ronda top works well in a meeting when layered underneath a blazer or knit jacket, but can also be just as good with a pair of jeans for a night out. (Genius details, like snaps to keep your bra straps in place, will also take your comfort level to an all-time high.) A simple white button-up, like the Lila shirt, brings C-suite chic but, all of a sudden, becomes casual-cool when you roll up the sleeves. If this is making your casual self sweat, think of these pieces as ways to instantly step up your style: Whenever you need to look like you really care, just swap in one of them for the usual.

Seek Out Patterns

The Didion top and the Oshima pant.

Patterns are ideal if you don’t want to come off as a try-hard. Revealing that you care a lot is deeply uncool, as I experienced firsthand in high school. But patterns are like the kids who’ll do your homework for you: They do the hard stuff and give you all the credit. Plus, patterns can make even a neutral seem interesting.

Take the indigo marble version of the Didion top. The blue-grey palette, watercolor details, and boxy shape work together to make it the centerpiece of your outfit, so you could probably pair pajama pants with it and be in the clear. With it, dark jeans, tailored pants, a skirt like the Dorchester, and even black leggings are fair game. Sit back and relax while the Didion top does the talking for you, conveying to everyone how capable and stylish you are.

A good print, like the swipe print on the Noel dress, can also give you the comfort of a classic silhouette—a wrap dress, in this case—while making it look completely reimagined. Plus, you can layer it with any solid piece, like a dark jacket, and it’ll have just as much impact.

Lean on Silhouettes

It’s a universal truth: At a certain point in our lives, we start to figure out what works for us. For instance, I know that I cannot go wrong with an A-line dress, because that’s just what fits my body type, which leans towards pear-shaped. I can tell in a glance that, say, the Jessica dress would be a good option for me. Understanding the styles that will instantly click with you will make a big difference, guaranteeing your comfort without going too far out of your way to get it. That would describe a fitted dress like the Gwen or something cinched like the Nanette. Whatever it is, stick to it and you can’t go wrong.

Play with Proportion

The problem with t-shirts (forgive me) is that they’re rather two-dimensional. There, I said it. They fall straight down from the shoulders. Proportion, then, both at top and bottom, will make all the difference. The perfect example is the Bergman top in ivy print, which features not only a delicate print but also a dramatic cowl in the back. It turns what would otherwise be a straightforward top into something more sculptural and unexpected.

The same goes for culottes, which offer the volume of a skirt with the ease of pants. The Zhou culotte offsets a more slim-fitting top or tank, and while it may seem a little daunting at first glance, trust us: It’s good.

Consider Your Accessories

A pair of heels is the equivalent of wearing a badge that says, “I care about this meeting.” The pain in the ball of your foot, however, is the inevitable reply of: “…but how much?” The Ella sandals present the best of both worlds, because while they’re ostensibly heels, they’re only three inches high and feature memory foam on the insole. 

Share this post. We dare you.


Deanna is a writer and editor in New York City. She enjoys reading, hiking, and not moving to the West Coast. Read more of Deanna's posts.

Read on.

Back to Top

Questions about styling or sizing? Chat with one of our stylists.