When I started at ELLE.com as senior news editor four years ago, it didn’t matter all that much what I wore. I cared about what I looked like, but on days when I had an I-have-nothing-to-wear meltdown, I could settle on a sweater-jeans combo and not stress about it. I rarely had meetings that included people outside of my own team, and if I needed to attend a meeting or after-work drink that prohibited me from wearing, say, sneakers, I knew about it in advance.

But, as I rose in the ranks at ELLE, I started getting invited to more unexpected meetings, asked to attend more last-minute events, and met more people whom I couldn’t wear clothes that were merely “comfortable” in front of. Getting dressed became more stressful.

Then I became Digital Director of Marie Claire and I had a wardrobe epiphany. I was a boss, so I should start dressing like one. I have meetings nearly every day now—ones that pop up on my calendar a half hour in advance. I find myself sitting across from fancy people with important jobs all the time—and, I’m one of them (and I should embrace that!), so I need to look and feel like I belong.

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I’m also super busy, so I don’t have time to stand in front of my closet freaking out that I have nothing to wear. I wanted a uniform of sorts—so I started weeding through my closet, picking out the things I loved, pieces that I could easily mix and match, and clothes that made me feel good. Then I identified the holes and made a mental list of things I wanted to buy. I realized I somehow didn’t own black pants or white button downs, the most classic of wardrobe staples, and those were the first items I invested in. Now, I’ve slowly started to build a wardrobe that’s put-together and comfortable—and makes me feel like a boss.

Olivia Malone

Dressing for Meetings With Potential Clients

Again, I didn’t own a pair of trousers until six months ago. Zero white button-downs hung in my closet. This is shocking to me now, because this pants + blouse combo has become my saving grace. My new go-to when I have to look polished (and get out the door) is a chic blouse, pants-that-are-not-jeans, a lady-bag, and a pair of heels.

kate spade new york Sam bag, $298 SHOP


Dressing for After Work Drinks With Friends

I have the luxury of having a job where I can look “cool” at work. Basically anything I wear to the office translates into an outfit that I can later drink wine in. The easiest way to make a quick-switch is, of course, with accessories. Swapping out my big laptop-lugging tote bag for a fun purse and putting on the pair of heels that lives under my desk (key for those last-minute meetings!) makes an outfit more night appropriate.

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Dressing for a Cover Star Fashion Shoot

Going to a cover shoot is always super fun—but never quite as glamorous as one would imagine. I always dress down (and wear comfortable shoes!) because inevitably I’ll find myself running around to grab something or plopping down in a corner with my computer. But! I still want to look nice, because at the end of the day I’m meeting a celebrity who I am pretty sure would totally be my best friend if we just had more time to hang out, etc.

Dressing for a Fashion Week Event

Fashion week is always interesting because people get a little more out-there with their lewks. I love something like a fancy fanny pack to make what might be a normal office outfit more capital-F Fashion….Plus, during fashion week being hands-free so you can have full arm range motion to take photos and videos and eat snacks on the go is a bonus.

Olivia Malone

Dressing for the Weekend

What do I wear on the weekends, you ask? Well, one of my favorite trends of the moment is athleisure (because who doesn’t want to wear leggings for two days straight?), but when it’s warm out, I’ve been trying to wear more dresses—it’s the easiest way to look like you tried, while still being laid-back and comfortable. And, of course, I choose sneakers, always.

All other clothing - Sally's own

Photography by Olivia Malone, Prop Styling by Todd Wiggins, Makeup by Ingeborg G, Hair by Takashi Yusa