6 Ways to Dress for Fall (In Any Office Culture)

Every office has its own rules—or, worse, some private code that no one actually talks about but somehow seems to exist. We toss buzzwords like "business casual" and "start-up vibes" around without a second thought, then find ourselves wondering how that woman on the third foor gets away with sandals.

When you're swamped with projects or starting a new job, the last thing you want to think about is planning and updating your work wardrobe. Still, admit it: you're tired of wearing that same button-down/blazer combo day in and day out.

That's why we've partnered with the fashion-savvy team at Trunk Club for a series of articles dedicated to tricky office fashion situations. But we wanted more than just their advice—we wanted proof that advice worked in the form of real women.

No two careers are alike, but we're all entitled to look good and feel our best. Below, you'll find six of our favorite working ladies (hint hint: one is our own Lauren McGoodwin), outfitted specifically for their unique companies, work, and schedules. For this round, we're covering the best looks for fall because layers are everything. 

Robin Zweig, Account Manager at Snapchat

Working for Snapchat means that Robin gets away with "office casual" most days—and that sneakers are totally OK. The proximity to the beach (yeah, we're jealous, too) also enables her to take walking meetings or meet clients for lunches or after work happy hours on breezy outdoor patios. The key is to have an outfit that's professional, comfortable for when she's on the move, and also has easy-on, easy-off layers for any unexpected temperature changes.

Why Trunk Club Chose It: "We could not be more into the athleisure trend, so we were really excited to show Robin this silky bomber. Its modern sportiness coordinates perfectly with this nylon crossbody, creating a cool, fashion-forward vibe that exudes confidence. (And given the context, we couldn’t resist the ‘GRL PWR’ tee.)"

Why Robin Likes It: "I die over the bomber jacket. I’m going to wear the shirt tucked in because I love t-shirts tucked into jeans. You can dress casual but look very put together when you tuck in a t-shirt. I like the shoes, too—my husband has the same Adidas shoes so there’s a tomboy element. I could wear this to work but also on a weekend and feel really comfortable." 

Raakhi Agrawal, Lead Growth Marketer, BCG Digital Ventures

Since our last Trunk Club post, Raakhi landed a new job at BCG Digital Ventures. Her new position as a growth marketer means a lot of client meetings. Think of them sort of like job interviews: they can make or break her next big professional opportunity. So her outfit? It's an essential part of making a great first impression. 

Why Trunk Club Chose It: "Working in a leadership position at a digital-focused company means Raakhi needs to look both commanding and contemporary. We combined those attributes by pairing a beautifully tailored suit with a bold blouse that shows a little personality."

Why Raakhi Likes It: "I like the fact that it's a professional look, but the shirt is unique. It makes it a not your typical black suit look."

Rachel Richardson, Blogger + Founder of Lovely in LA

Rachel's runs the style blog Lovely in LA so keeping up on the latest fashion trends is essential. Plus as a blogger, Rachel's meetings happen as much over cocktails as they do during the work day. That's why fast day-to-night changes via accessories (and the occasional leather jacket) are a must. She never knows what a day might look like. 

Why Trunk Club Chose It: "Deep red is the perfect fall color for dark-haired, blue-eyed beauties like Rachel. It’s a powerful yet inviting hue that’s sophisticated enough for meetings and stylish enough for happy hour. Simply swap a few accessories, and you’re set for the entire day."

Why Rachel Likes It: "I love the color first of all—it's great for fall. It’s always been one of my favorites so I’m glad to see it’s back in trend and staying there. [The dress] came with a belt, but that’s a dressier element, so that’s what I would wear for an evening event. For a day meeting, I'd dress it down—taking the belt off, bringing the accessories down a touch, and adding a denim jacket. I'd wear the same shoes regardless—a lot of time you don’t want to carry around a bunch of different shoes so it’s great to find a pair that can transition from day to night. I’ll often just get a last-minute text that’s like 'Hey, can you meet me here?’ and I’m like, "Great." That's why I always keep a jacket in my car and a change of shoes. I also carry a couple of different lips with me because that’s an easy way to get ready for an evening event."

Lauren McGoodwin, Founder + CEO of Career Contessa

The nice thing about running your own startup is that you can make your own rules to a certain extent. But since we're a career advice platform, Lauren also has to make sure she's taking her own advice when it comes to big meetings or speaking engagements. Cue the refined leopard prints—a little adventurous but also put-together.

Why Trunk Club Chose It: "Lauren said she likes to keep up with trends, but in a way that doesn’t feel too distracting for the office. This silk Equipment blouse transforms leopard print—one of fall’s biggest trends—with muted tones of navy and blush that are so chic we can hardly stand it."

Why Lauren Likes It: "I always like that perfect blend of high and low. Cigarette pants are classic but easy to throw on and go, and then there's the animal print which is a fun take on fall trends that doesn't go too far in the 'trendy' direction. For me, work wardrobe staples should be the kind you can wear for years—they're investment pieces. I can see myself reaching for this button-down repeatedly." 

Christina Topacio, Founder of Jig + Saw

Christina runs one of a resource center for female entrepreneurs and creatives based in Los Angeles. Her days often include meetings around town. As the weather turns, commuting means possible rain and changing temperatures between the AC in her Uber, chilly days on foot, or overheated offices. A flexible outfit is essential. 

Why Trunk Club Chose It: "Christina is a really fun, creative woman, so we knew she’d be open to some out-of-the-box layering. We started with this tiered dress, but skipped the standard open-front sweater in favor of a cashmere pullover. A few bangles to play up the metallic threads in the dress, a sturdy pair of designer boots, and bam—you have a look as fierce as it is functional."

Why She Likes It:  "Because I’m based in California, the idea of wearing a chiffon dress with a sweater on top allows for when it's cold outside but maybe too warm in the office. Honestly, layering is really key in Los Angeles. And then the Acne boots are too good. For my personal style I like to be really feminine but to add in a masculine energy. That’s my vibe. So the boots totally complement the feminine dress."

Jenna Greene, Founder + CEO, Forward Collective

We had the pleasure of interviewing Jenna back in the early days of Career Contessa about her work in marketing. Now she's taken the plunge to start her own consulting company, the Forward Collective. Her work means a lot of travel—you'll often find her hopping flights between Los Angeles, New York, and Chicago. Layers help keep her warm on frigid planes and adapt to the changing temps across the country. 

Why Trunk Club Chose It: "LA, Chicago, New York… three cities with three pretty distinct fall climates. In that spirit, we dressed Jenna in light- to medium-weight layers that look as put-together on their own as they do, well, put together. Bonus: the bag is roomy enough to stash reinforcements such as a hat, scarf, and gloves, should the temps really start to dip."

Why Jenna Likes It: "Since I travel so much, I really like to be comfortable on the plane. These jeans are really stretchy so they’re perfect. I'm always cold on flights, too, so the sweater is a must. Nothing's too tight but the outfit still has a kind of structure. The jacket gives a little structure, too. It's the perfect balance."