YouTube Millionaires: Ashley (aka ‘Bestdressed’) Teaches The Internet How To Do Fashion With A Combo Of “Uncensored Personality” And Expertly Crafted Videos

By 05/02/2019
YouTube Millionaires: Ashley (aka ‘Bestdressed’) Teaches The Internet How To Do Fashion With A Combo Of “Uncensored Personality” And Expertly Crafted Videos

Welcome to YouTube Millionaires, where we profile channels that have recently crossed the one million subscriber mark. There are channels crossing this threshold every week, and each has a story to tell about YouTube success. Read previous installments of YouTube Millionaires here.

Ashley (aka ‘bestdressed’) wasn’t always a fan of fashion. She didn’t become enthralled with it till her sister strongarmed her into watching Project Runway. Even after Tim Gunn taught her the appeals of being best-dressed, she didn’t go for runway fashion — she went for thrift.

And thrifting is what brought her to YouTube.


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Well, sort of. Ashley (who goes by first name only) had been a fan of YouTube for years, and had started and ultimately deleted several of her own channels. But until she found fashion, she didn’t have a solid content direction. Fashion was the click of the key into the YouTube lock. Suddenly she knew how to meld her passion for film, her drive to make YouTube content, and her fashion hobby.

Like that fashion hobby, YouTube quickly became a full-time job. On the fashion side, Ashley’s casual reselling of thrifted items became her business, On the YouTube side, she became a one-woman production team making a range of weekly content, from vlogs (she calls them “chatty” videos) to videos about the essentials of fashion to often tongue-in-cheek how-to’s about a variety of subjects.

For the past few years, Ashley balanced both full-time pursuits with attending UCLA, from which she recently graduated with a degree in film, TV, and digital media. Now she’s throwing herself into YouTube — and that’s a good thing, because she’s also a recent YouTube Millionaire who’s already surpassed 1.5 million subscribers in the couple weeks it took us to publish this piece.

Check out our chat with her below.

Tubefilter: How does it feel to hit one million subscribers? What do you have to say to your fans?

Ashley: I’ve always been big on milestones. Probably as a result of constantly overworking myself, I look toward milestones as a way to prevent myself from burning out. When I worked three part-time jobs in high school, I told myself I’d finally be happy when I went to college. When I cried myself to sleep in college more often than I’d like to admit, I told myself I’d be happy once I found a solid career. Once I reached 100,000 subscribers on YouTube, I told myself I’d be happy once I reached a million. Honestly, just like every other milestone I thought would change everything, reaching a million was rather anticlimactic. The night I hit a million, I treated myself to a $10 salad and went to sleep.

The way I think of it, my job is and has always been to sit in front of a camera every week and make the best video I can. To that extent, my life is exactly the same as it was three years ago when I started — I guess I just get all these nice perks now. That’s the head-down-keep-working approach I strive to maintain. I cannot express my gratitude for everyone who watches me and the life they’ve given me, but at the end of the day, it’s not my job to get caught up in the numbers or rave about how much I love my fans or even hype myself up in articles like this one. It’s about making a damn good video and doing it even better the next week.

Tubefilter: Tell us a little about you! Where are you from? What was your college major? How did you get into fashion–and, more specifically, how did you get into fashionable thrifting?

Ashley: I’m from Ellicott City, Md. Never heard of it? That’s okay, no one has.

I grew up an artsy kid raised by a chemistry and physics Ph.D., so safe to say I spent most of my formative years dreaming about moving to a big city and pursuing a career in art or design or photography. Without a single film class at my high school, I literally didn’t realize that being a director or screenwriter was a real career path until senior year. I knew that film was a risky career to pursue, so I promised myself I’d only pursue it if I got into one of the top three film schools. Lo and behold, I got into UCLA, so I broke my parents’ hearts and chose UCLA’s film school over Stanford. I just graduated with my bachelor’s in film, TV, and digital media this March.

I used to be a major tomboy (we’re talking khaki capris and a T-shirt every day level tomboy), but my sister made me watch Project Runway every night until, like five seasons later, I finally fell in love with fashion. I blame Tim Gunn.

I got into thrifting two summers ago, when I got my wisdom teeth removed. Deep in chipmunk mode, I needed a distraction, so I tried thrifting for the first time, and to my surprise found some actually cute stuff. Since I was still working at an ice cream store for minimum wage, I started a side hustle reselling thrifted clothes on Poshmark and Depop. That little business has blossomed into my website ( today.

Tubefilter: What made you pick YouTube as the place to share your content? What did you hope your channel would be when you started it?

Ashley: I grew up watching YouTube, so I always itched to start a channel of my own. When I was in third grade, I actually started my first-ever channel called PipeCleanerStudios where I uploaded animations of a pipe cleaner dinosaur named Charlie and got like two views. Eventually I started recording knockoff CommunityChannel stand-up, but quickly realized how embarrassing that was and deleted my channel.

The second time around, when I started this channel my senior year of high school, I genuinely just wanted an outlet for my love for fashion and a way to participate in the YouTube community I grew up with. I remember writing in my journal that I wanted to be a graphic designer, architect, or YouTuber, but never in my wildest dreams did I think that last option would come true.

Tubefilter: What do you think makes your content stand out despite all the noise on YouTube?

Ashley: The way I see it, there are two schools of fashion and beauty YouTubers: the old-school picture-perfect guru, and the relatable, “effortless” vlogger. I don’t quite fall into either category. I’m honest about my flaws and awkward moments, but I’m also an absolute tryhard. Not in the sense that I spend hours caking on foundation and practicing my on-camera smile, but in the sense that I spend days editing and perfecting every cut, color correction, and composition. I think it’s that combination of my uncensored personality and thoughtfully edited videos that makes me stand out.

I also feel like whether it’s through a fake smile or self-deprecating jokes, a lot of YouTube videos feel dumbed down to the least common denominator of entertainment. I refuse to do that — I want to show my viewers you can love fashion and have informed political opinions and care about larger issues and have stupid brain fart moments and get straight A’s and have an existential crisis all at once.

Tubefilter: You have quite a mix of content, from hauls to the lifestyle vlogs to how-to videos. Do you have a content strategy that directs what kind of video you post? Like, do you do a vlog this week, then a haul this week, etcetera, or do you go with the whimsy and post what you’re feeling?

Ashley: When I was still in college, it was really whatever I had time for in between classes and jobs. Now that I’m full-time, I keep a seemingly neverending list of video ideas in my notebook. I categorize them into fashion or lifestyle, chatty (a sit-down video) or involved (more edits, takes over three hours to film). I’ve never found success in scheduling my videos weeks in advance, so I pick whatever I’m most passionate about week to week, but I remain cognizant of the need for balance and variation.

I aim to never go a month without a fashion video, and never go three weeks in a row without an involved video. Thursdays are my Big Upload Day, so peak quality only then. I occasionally upload on Sundays as well, which can be more chatty and casual in the weekend spirit. I also have a category in my notebook for “big projects” such as short films and room makeovers, which take months to plan and film, so I work on those during the weekend in between filming my weekly videos.

Tubefilter: What’s your production process like? How long does the average video take you to make, from conception to posting?

Ashley: I’ve actually been getting into tracking my time lately because I was curious how much I actually work. This week, I spent 22 hours editing, 19 hours filming, nine hours on emails, meetings, and calls, eight hours taking and posting Instagram photos, and three hours developing presets. So, around a 60-hour workweek.

I generally film on Mondays, film B-roll and pickups and begin to edit on Tuesday, do a full day of editing on Wednesday, and then wake up bright and early on Thursday to finish the edit (usually another five hours). I try to take a real weekend so I can unwind, but I usually end up working on my aforementioned big projects over the weekend and/or editing a vlog or bloopers vid for my second channel and/or planning for the week ahead.

As far as my production process, I’m my own cameraman, editor, gaffer, and crafty. I usually write a general outline for my video in my notebook. The day I film, I spend the morning getting very caffeinated and mulling over what shots, edits, jokes, etcetera the video should include. I don’t listen to music or podcasts or talk to anyone for those few hours — just think. For a 15-minute chatty video, I usually record around three hours of footage. For a room makeover or weekly vlog, I have five to six hours of footage. I do a rough cut immediately after I film, while everything I said and did is still in my head. I learned that from Guillermo del Toro — he rough cuts his scenes the same day he shoots them since the best takes are still fresh in his head, and saves so much time that he has a fine cut of a feature film a few months after production ends. After my rough cuts, it’s just hours and hours of replaying, refining, cutting everything out that doesn’t add value.

Tubefilter: When did you start noticing your audience really picking up? How are you growing your audience?

Ashley: It’s been somewhat exponential with a few big waves. I remember two summers ago, one of my first thrift hauls got 200,000 views, which I thought was a huge deal. That helped me get my feet off the ground from less than 1,000 subscribers to around 25,000, which in turn motivated me to start making weekly videos. I haven’t missed a week since. My bedroom makeover is now sitting at over 6 million views, so that’s been a huge contributor, along with some of my more high-effort fashion videos like 50 Outfits for When You Have Nothing to Wear (below) and How to Put Together an Outfit 101.

I’m trying to grow my audience by just making better and better videos, with fewer and fewer sponsorships. Luckily, I’ve never grown from clickbait or lazy videos, so I’m going to continue mixing chatty vids and vlogs with those high-effort, useful videos that often have farther reach.

Some of the big videos I have planned honestly are things I’ve never seen on YouTube before, so they could perform well or completely flop. But I know either way I’m excited to make them, and that’s what matters most. You have to build something you love, then the audience will come eventually. It doesn’t work the other way around.

Tubefilter: What else do you get up to in your daily life?

Ashley: The weird thing is that I’ve turned nearly all of my hobbies into my job: filmmaking, photography, fashion, thrifting, comedy, writing, interior design… Sometimes there’s not much left for me to do as a hobby. Even though it’s kind of my job, thrifting and listening to music is one of my favorite ways to relax. And audiobooks. I could sit and listen to books for weeks on end if you left me unchecked. And, of course, the best feeling in the world is staying up late talking to someone, whether it’s my boyfriend (let’s be honest, it’s usually him) or a good friend.

Tubefilter: What’s your favorite part of making content specifically for YouTube?

Ashley: Having complete creative control over my videos, from concept to filming to editing to distribution to “marketing” (the thumbnail and title), is my absolute favorite thing about YouTube. Nobody tells me what to make and what words to censor and what jokes are too weird. And at the end of each week, I can watch my video back knowing it’s something I created by myself from scratch. It’s a little bit of me, transposed into a video.

Something I learned early on in film school is that creative control is more valuable than money. Directors and writers forgo huge studio budgets in exchange for smaller productions free from interference from executives and financiers. Beyond the film industry, in a world where most jobs consist of some type of vague computer work for a corporation, it’s increasingly rare to have a direct connection to the thing you spend your life working on.

Tubefilter: What’s next for your channel? Any plans looking to the future?

Ashley: Oh boy, where to start! I always have 10 times more ideas than I have time to actually do them. I have a couple exciting new projects in the works that have been lifelong dreams of mine, so I guess you’ll just have to wait and see… It’s always been a goal of mine to have a business outside of YouTube so I’m no longer dependent on sponsorships or have to worry whether my videos get demonetized, so that’s hopefully not too far on the horizon.

As for my channel, I’d love to continue to push my videos to new and more cinematic formats, make mini documentaries about issues I’m passionate about, direct a music video, start a podcast, finish my second screenplay, and think of ways to use my skillsets and all the opportunities I’ve been handed to help the people who need it most.

You can add yourself to the ranks of Ashley’s more-than-a-million YouTube subscribers at her channel

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