I Asked AI to Style Me…The Results Were Shocking.

Vanessa Van Edwards used AI to pick a stage outfit for Dave Ramsey's EntreLeadership Summit, testing whether the tool could nail camera-friendly fabrics, jewel tones, and a $300 budget. The AI suggested emerald dresses, sapphire suits, and cobalt wide-leg pants from brands like J.Crew and Mango.
Chapters
I have this big event for EntreLeadership Summit with Dave Ramsey, and I need a good stage outfit. Now we have AI, so I'm gonna ask AI to be my stylist. I found that fashion cues, clothing cues, they matter. They signal professionalism, they signal competence. If you are a little bit fashion forward on stage, it makes people pay attention because they feel like it's new information. I've also noticed anecdotally that people take more pictures. The best gift for me as a speaker is when someone holds up their phone and takes a picture of me on stage or the thing that I'm teaching. They post more, they tag me more, which at the end of the day I want to help more people. It's asking some questions. What outfit silhouette do you want to focus on for stage? I do love a tailored dress, but I also would wear a suit, but I also wear a blazer, so all of the above. Any color direction you prefer or want to avoid? Love a bold jewel tone. Oh, I'm gonna try to keep it like affordable. I'm gonna say under $300. Has to be comfortable. Ha! Weird rules for stage is, uh, any kind of tight-knit fabric like cable knit doesn't work. It blurs on those big IMAG cameras. Usually I'm above the audience, so anything where someone could see at my skirt, that's a no-no. Very strict rules from the AV team on the sound of your jewelry. I could only wear one bracelet, for example, because I couldn't click. I've also gotten backstage about to go on and the AV team says, "Your earrings are too dangly." They can only go down about a centimeter because if I wear the over-the-ear TED Talk mic, it actually hits and clicks on that microphone. All right, this is the audience I'm dressing for, Entrepreneurship Summit. Yep, I will be in Orlando. Please join me, by the way. I'd love to see you there. You can see what outfit I pick. Okay, option 1: emerald poncho sheath dress, camera-ready classic. Sapphire suit blazer, wide trousers. I like it. Magenta blazer— no, AI, you've gone too far. I wouldn't wear magenta is because I found that there are certain outfits that that are too bold and I just turn off some audience members. I have found that that mindset translates into their ideas about the content. So if I show up in a magenta blazer, I might think that's fabulous. AI might think that's fabulous. You might think that's fabulous. But someone in the audience is like, "Pfft, too much." I think that there's like a formula of I want to come out and be just edgy enough and new and bold that people are like, "Mm, I'm going to lean in and pay attention, but also I'm still safe." it's still going to be comfortable. This isn't going to be too out of the box where you're going to be too afraid to try it. Clothing sometimes speaks before I do. They're making all kinds of judgments. Okay, it's finding a lot of J.Crew, a lot of Mango. By the way, Mango has a fitted blazer in fuchsia. Let's see if it comes in wine. Or J.Crew going out blazer, a Banana Republic tailored stretch blazer and a wide leg pant in cobalt. See, like, that's the win. Oh my gosh, my favorite, Quince. It just recommended the Quinch Stretch Pont Sheet. I have to go look it up. I have a ton of their stuff. That's going to be my first look. I'm going to look there first. Nude or black block heel pump. I love when I can wear a shoe I already have. So which would you like to see me in? Uh, unique colored pantsuit in wine, a unique colored pantsuit in cobalt, blazer with a wide trouser, a fitted dress in emerald, wine, or cobalt, or grab bag? Should I surprise you? You don't like any of those options? Follow me for part 2.










