Tosca Webb
Q What do you do?
“I help brands and founders communicate who they are, what they value, what they do, and why people should care.”
As a social media strategist, I bring brand stories to life online through content creation, community engagement, account audits, analytics, and creative problem-solving. Not to toot my own horn… but I'm really good at what I do :)
Q What steps did you take to get to where you are now?
Whew, where to begin!? I founded my own brand in 2017 called Dress Up Collective, which was the take-off point of my career. Dress Up Collective began as a DIY fashion events series that invited guests to come and play dress up with a curation of 300+ pieces of vintage clothing that I hand-picked. The goal was to create a safe and welcoming space for people to explore clothing, free of judgement. The brand took many shapes and forms over the years, eventually leading to an e-comm site, multiple merch drops, art exhibits, media series, and finally, a studio space.
From there, I was hired as the social media and brand partnerships manager at LA-based media company, Stylelikeu. This was my dream job, and it taught me more than I could’ve hoped for. I owned social strategy and managed end-to-end brand partnership campaigns. I got to work with incredible talent like Adrienne Maree Brown, Paulina Porizkov, and Amanda Seales, as well as lead viral social campaigns with brands like Free People and Dipsea. It was exciting and fast-paced and I wouldn’t trade the experience for the world.
Eventually, I began thinking about ways to broaden my skillset and was really excited about the idea of working with multiple brands and founders all at once. So, I began freelancing full-time in 2023 and, three years later, I’m still obsessed with my job.
Q How do you stand out in your field?
My approach to business is people-centric, and I care deeply about creating opportunities for inclusivity and storytelling. My first priority is always people. Ultimately, we all come online to connect, learn, feel inspired, and have fun. When I hold these learnings as pillars at the core of my work, it always leads to success.
Q What are you working on right now?
All of my friends are artists and musicians, and as of late I’ve been so excited to take on more creative endeavours to help with their projects. This looks like lots of video editing, creating social content, and building album rollout campaigns. In my personal life, I’ve recently dusted off my sewing machine and am determined to become a bonafide thrift-flipper. Wish me luck!
Q What’s your style?
Expressive, inquisitive, and playful! The best representation of this would be my brain-child, Dress Up Collective.
Q Out of all your slashies, which one do you wish you could do more often?
My favourite part of my job is being on-set and capturing video and photo content. The bulk of my home videos from when I’m a kid were me behind the VHS camera, and that obsession has carried through into my career.
Q What is frustrating you right now?
Ugh, admin work! All the boring stuff… doing the books, blah blah blah.
Q If you could hire someone for $20/hour, what would you have them do to make your day easier?
The admin work 🫠
Q What do you wish you could have told yourself, when, and why?
Be gentle with yourself <3 Trusting your gut to follow your passions is admirable, and success looks different to everyone. My 16-year old self would be proud of me, and that’s all that matters!
Q If you could talk to an expert to gain more insight on something, what would it be about?
I recently had a call with Shakaila Forbes-Bell who’s a Fashion Psychologist, and wowwww! Talk about pursuing your passions and following your instincts. The way she’s created her own career without a linear path to success is so inspiring. I’d love more time to pick her brain about fashion psychology - I find it fascinating. Also, verrrry inspired by Lola Adewuya’s work and repositioning herself as a ‘multi-hyphenate’. She talks about non-linear career paths, and there’s a very poetic quality to her way of thinking that resonates.
Q What kind of opportunities/projects are you looking for?
Ultimately, I’m fuelled by people and projects that inspire me and feel aligned with my values and worldview. I’m curious about connecting with each other in an increasingly digitized world, and I’m especially interested in (and manifesting!) working with women and/or queer-owned, mission-driven brands in the fashion, arts, media or culture space. Anything hyper-creative and imaginative… I’m in!
Q Describe your ideal job/client/collaboration.
I’m excited to work with brands, artists, and founders who are down to take risks and try new things on social. I really believe that in order to cut through the noise (and there’s a lot of it), we need to be fine-tuning what makes your brand special and then communicate that in a way that people are genuinely going to connect to.
Q What is your rate?
My retainer packages typically start at around $1,200/month for social strategy and management, but I’m always open to chatting if you have budget constraints or a smaller project that’s more suited for an hourly basis!
Q How should someone approach you about working together?
You can email me directly at toscamwebb@gmail.com with a short description of the brand/project, scope, budget, and relevant links :) Can’t wait to meet you!
Q Who is a creative you admire?
My dear friend, Betsy-May Smith. She’s an art director and truly my creative soulmate. Follow her, hire her, be inspired by her!
My little sister, Margaret Webb. She’s a jewelry designer and I’ve genuinely never received more compliments than when I’m wearing her designs.
And last but not least, my sweet husband @james__clayton. He’s my favourite musician.
Q Oh! and… how do you stay creative?
Have FUN, laugh a lot, and prioritize time with friends & family, always.
This member profile was originally published in March 2023, Updated June 2026.