Step into the universe of the coolest creatives in the fashion industry with our series My World, where readers will discover how the top stylists, designers, and tastemakers built their careers; their favorite restaurants, beloved albums, and fashion finds; etiquette rules they stand by; and so much more.
Running from showroom to showroom, fueled by caffeine and candy, Molly Dickson is Hollywood’s most dynamic and versatile stylist. How did she get there? Patience and hard work. “It takes time!” Dickson told Who What Wear. “I think a lot of stylists expect to be styling a cover shoot after one month or working with a celebrity right away. There isn’t a manual for this job, and it’s a lot of hard work. To get my first client, it took me almost nine years. First, I was an intern, then an assistant, and then I went out on my own. My best advice is to work hard, be kind to everyone, and be patient.”
This approach has served her well, as evidenced by her long list of celebrity clients, including Lana Del Rey, Ariana Greenblatt, Sydney Sweeney, Keke Palmer, Sadie Sink, and many more. Ahead, get a behind-the-scenes look into Dickson’s world, including her favorite wardrobe staples, what she’s watching and listening to, where she’s traveling, and of course, her best styling tips.
What is a typical day in your life?
One of the most fun things about my job is that every day is completely different. I can see how someone may not like that, but for me, it’s a perk. I can say with confidence I’m never bored. Tired? Maybe. But [I’m] never bored. A typical day is waking up early and checking all emails. Being in L.A. means we are way behind Europe and NYC, so my inbox is already full. Once I’ve scanned my inbox and checked in with my team, I’ll head out for the day, which is either straight to the office, running around L.A. for pulls, or off to a photo shoot. I’m continually checking emails throughout the day and prepping for fittings, which is a mix of emailing requests, physical pulls at various showrooms, and searching for that perfect piece. I love the hunt, and I’m committed to it! It sometimes still surprises me how much research is required in styling; it’s sometimes the bulk of my day. One of the most stressful parts of the job is the amount of jobs you are often balancing at once. It’s not uncommon to be set for one job and prepping three or four other jobs simultaneously.
Growing up in a small town in North Dakota, could you have imagined yourself building such an impactful styling career?
I can’t say I dreamed of this as a kid in North Dakota, but growing up on a farm really instilled a strong work ethic in me. I remember being young and seeing my grandpa and dad wake up before sunrise and working until the middle of the night during harvest, and their commitment made me understand how valuable hard work is.
Your first break was at Marie Claire in 2009 as a fashion intern. What was something you learned there that has stuck with you through your solo career?
I think everyone should intern! My advice is to work hard and be invested. Be the first one there and the last to leave, and no task is too small.
What do you enjoy about working with Gen Z clients like 18-year-old Ariana Greenblatt? How is it different styling women early in their careers versus more established names?
I love working with young talent! I started working with Sadie Sink when she was 14, and she’s 23 now. It’s fun to work with the younger girls and experiment with looks as they develop their style, while making sure it’s age-appropriate. I love being able to work alongside them and start to craft their personal style both on and off the carpet. With Ariana, there is no one cooler, truly. She has such a clear vision for what she wants to wear, and she is one of the lucky ones who can wear anything and look incredible.
What has been your favorite Keke Palmer outfit you’ve styled and why?
Keke is so fun to work with. She loves fashion, is happy to take risks, and is a huge vintage fan, which makes creating looks very fun. Although it’s difficult to choose, my favorite is the vintage 1993 Chanel Haute Couture look she wore to the BET Awards this summer.
You work and plan for so many different kinds of events, from artist tours to red carpets to fashion campaigns. What is it like going from one to the other?
I have a bit of ADHD, so I actually love having the versatility of doing different jobs every day. Music is a whole different world, and the styling needs are very different, especially for a performance. With music, you have to think about movement, quick changes, mic packs, multiples… It’s all a puzzle that I love working on. Campaigns are great because you’re often working on a large brand moment and with super-talented teams, which is always fun to see how other people see things. Then we have press tours and premieres, which each require something of their own special sauce. In the end, I am so grateful I get the opportunity to work across them all because it’s all truly so fun.
How would you describe your personal style?
Ironically, if you saw what I wore in front of my clients at fittings, you would think I would need a stylist! Admittedly, my focus is always on making sure my clients’ looks are perfect, and I probably spend less than a minute or two on my personal appearance. I always prioritize comfort, and I am generally in my dad’s old Hanes T-shirt or my boyfriend’s sweatshirt and a pair of jeans.
What are your go-to everyday pieces?
A good pair of comfortable, oversize jeans. I don’t like to wear anything too restrictive, especially because my job requires so much manual labor—carrying garment bags, on the floor getting clients’ shoes on, etc. So glamorous, right? But truly, the schlepping and constant movement are why comfortable pieces are key.
If I can squeeze in a workout, it’s Barry’s bootcamp followed by a sauna/cold plunge contrast therapy at my boyfriend’s business, Likeminded. A lot of the time, I will also just wear my workout clothes to the office with the goal of hitting up a last-minute class whenever I have a window to step away. If I’m not in workout clothes, I’m in my classic uniform: oversized t-shirt or cropped tee, baggy vintage Levi’s jeans or Skims sweatpants, and Salomon sneakers.
What are your tips and tricks for styling boots for fall and winter?
Fall is my favorite season, and that means I’m pulling tons of boots! I love using shoes to make a statement. I love juxtaposing a girly skirt or dress with a more masculine shoe. In summer, I do it with sneakers, pairing a pretty, delicate dress with Salomon sneakers, and in the fall, I love something similar but with a really strong boot. At the moment, I’m very into long skirts in general, like a simple, silk skirt that hits mid calf, paired with a tough, statement boot. It’s the perfect balance of feminine and cool. If the skirt or dress has a thigh slit, I like to pair it with a form-fitting thigh-high boot. If the skirt or dress is more flowy, you can also pair it with a chunkier boot like the Chloé Dakota Boots. I’m also very into vintage cowboy boots worn with perfectly tailored jeans and a simple tank or knit to get a little western feel.
Skims
Cotton Fleece Pants
You travel to so many amazing places because of your job. Do you have a favorite city you’ve visited? If so, what’s a favorite coffee spot or restaurant?
My friends always laugh at me because I am a huge Starbucks fan. Yes, there may be better coffee available, but my job is very chaotic and can be all over the place, especially with travel, and a Starbucks vanilla latte is the one constant thing in my life no matter where I am in the world. I recently went to Sardinia, Italy, with Sydney’s glam team, and we went to this amazing pizza spot: Le Specialità. I highly recommend it!
A favorite hotel that you’ve stayed in?
I stayed at The Peninsula in London recently, and it was amazing. When I’m traveling for work, I judge hotels by how well they handle my deliveries (as a stylist, I get so many packages/garment bags), and The Peninsula had individual mailboxes outside each room for all packages. It was so convenient, and the service was incredible.
On flights, are you a movie or book person?
Let’s be real. On flights, I pass out before we even take off. I never get Wi-Fi, which drives my team nuts, but it’s the only time I am able to shut off and sleep!
On the topic of travel, how often are you able to visit your hometown in North Dakota?
I was just there over the Fourth of July, and it was so nice. I try to go back a few times a year to see my family and reset. North Dakota is such a departure from what life is like in L.A. that it’s the best reset. [There’s] nothing like a tractor and a field to bring me back to reality, but in all seriousness, it really helps to ground me, and it’s a nice reminder of how simple but enjoyable life can be.
If anyone finds themself in ND, what is a local (maybe hidden) gem you recommend they check out?
Absolutely! Widman’s Candy Shop in Grand Forks (106 South Third Street Grand Forks, ND 58201). Get their milk chocolate chippers, which are actually chocolate-covered potato chips, and thank me later! For a bite, definitely go to The Toasted Frog and order their fried pickles, and of course, I love my grandma’s homemade chocolate chip cookies. Truthfully, if you ever made it to Gilby, North Dakota, she would probably be happy to host you for some too.
What are you watching right now?
The Summer I Turned Pretty.
What about music?
I like old-school country, like Garth Brooks, but I’m probably listening to whatever my boyfriend has on in the background. He has great taste in music.
Do you have a favorite Lana Del Rey song?
I couldn’t pick a favorite. I love everything she does. She sang “Country Roads” at Stagecoach this year, and I almost cried because it was so beautiful. She is truly incredible.
Is there a podcast you listen to or a book you’re currently reading? Anything you recommend?
I love Elin Hilderbrand books; I think I have every single one she’s written.
What is one styling rule that you stand by?
Tailoring is key! Everyone should have a good tailor; it’s the little tweaks that will make all the difference. Remember, clothes aren’t designed to fit you perfectly. You have to make the tweaks, and if you’re spending your money on something, it should fit you well. You can also have fun with a tailor. Suddenly, that “too big for you” dress you thrifted is now a cute two-piece set.
What is your biggest pet peeve?
Logomania.
What is your favorite on-set snack?
I can’t say this is the picture of health, but if I’m being honest, it’s Red Bull, candy, and Starbucks vanilla lattes—emphasis on the ‘s’ on lattes.
What is something overrated and underrated in your mind?
Overrated: high heels. Underrated: undergarments. They can make a huge difference!
What are your favorite things to give and receive as gifts?
I try to be thoughtful with my gifts and really think about the person and what they would like. If someone says something, I try to note it down so I’m ready when the occasion comes. I wouldn’t say gifts are my love language per se, but someone once gifted me a purse that was prepacked with Skittles in it, which was so thoughtful.
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