Branding
Design

Self-Care Shirts

Self-Care Shirts hand-drawn mental health apparel brand
Client
Self-Care Shirts
Year
2025–present
My role
Founder — illustrator, brand designer, web designer & developer, copywriter, marketer
Sector
Ecommerce · Mental health
Services
Brand identity, 50+ hand-drawn product designs, custom Shopify theme design and build, paid user-testing program, SEO and structured data, email and paid acquisition, content strategy, free mental health resource library
Page one of Google at a domain authority of 10, 4.96 from 159 reviews, $3,394 donated — every discipline run by one person.

The brief

Self-Care Shirts is the project where I'm the client, and the brief I wrote myself was simple to say and hard to do: build a mental health apparel brand where the conversations start naturally — because someone saw a shirt, a sticker, or a drawing and felt understood. Every design hand-drawn. Every order supporting the 988 Lifeline and The Trevor Project. And every discipline — illustration, brand, web, copy, SEO, email, paid ads, customer service — done by one person, because there is no team.

It's also the project where I can show my work all the way down, because nobody was watching over my shoulder except the market.

Why it was hard

  • The subject is a wound, and the medium is a t-shirt. Mental health apparel can go wrong in a hundred ways — trivializing, trauma-dumping, or preaching. Every design has to land as permission, not prescription. The voice took years to calibrate: warm, matter-of-fact, wit pointed at myself and never at the wearer.
  • Ad platforms restrict the category. Meta classifies mental-health-adjacent products under “personal hardships” and limits their delivery. I had to build an acquisition system that stays honest to the brand and survives policy — including knowing which restrictions to accept rather than write around.
  • An unknown brand asking strangers for their credit card. No retail presence, no team, competing against faceless drop-shippers — trust had to be designed, not assumed.
  • “Is this AI?” Hand-drawn work now gets accused of being generated — the exact opposite of the brand's premise. The proof existed; it had to be made visible.
  • Commerce and care pull in opposite directions. A crisis resource next to a buy button is a design problem most brands never have to solve. Getting the donation model, the free resources, and the store to feel like one coherent act — not a store wearing a cause — was the hardest brief inside the brief.

What I did

  1. Drew the catalog. 50+ original designs, every one by hand — apparel, stickers, and prints, organized around feelings rather than product types.
  2. Built the voice before the store. A brand language of permission-giving and self-directed wit, carried through products, email, and Healing Out Loud — the blog where I publish two personal essays a week on mental health and running a business of one.
  3. Designed and hand-built a custom Shopify theme. Not a template: a product page with a “get this design as” format switcher, collection pages filterable by feeling, a flat-goods template, and a custom cart drawer — built for how people actually shop for meaning, not SKUs.
  4. Paid eight strangers to tear it apart. Before launch I commissioned a paid user-testing panel with one instruction: tear it apart. They found twelve real issues — including a color-swatch bug that was silently killing sales. I fixed all twelve in forty-eight hours and shipped. Every tester said they'd trust the site with their card; all eight independently cited the same trust signal — the section where I say it's just me.
  5. Did the unglamorous technical work. Consolidated three competing structured-data voices into one clean schema stack, added FAQ and breadcrumb markup, and rebuilt the Google Merchant Center feed to a 98.7% product approval rate.
  6. Built the free side of the brand. A mental health resources hub — hand-drawn printables, a 30-second check-in tool that stores nothing, guided breathing and body-scan videos, and a group facilitation guide — free, no email required. It's the brand's service arm and its most-linked asset.
  7. Made the hand-drawn provable. Turned the “is this AI?” accusation into a trust asset: timelapse videos of designs being drawn, start to finish, now running on product pages and in ads.
  8. Ran acquisition like a CFO. Contribution-margin math, a true break-even ROAS, two-week judgment windows, and the discipline to cut what doesn't clear the bar — including my own favorite campaigns.
  9. Made the mission auditable. Every order supports the 988 Lifeline and The Trevor Project, with a public running total — donations as a receipt, not a marketing claim.

What changed

  • Page one of Google for “funny mental health shirts” — at a domain authority of 10, outranking sites with many times the backlink profile, on relevance and structure alone.
  • 159 reviews, 4.96 average.
  • 73%+ email open rates, twice running — a list that actually wants the mail.
  • Paid acquisition relaunched above break-even in week one, on math I can defend line by line.
  • Featured in nine outlets, including MSN and AZ Big Media.
  • $3,394 donated to the 988 Lifeline and The Trevor Project — and counting.
  • 5,313 reminders shipped. The brand counts units in reminders, not products — because that's what they are.
Reading your story made me trust you more.
Paid user-testing panelist, pre-launch review
Selected visuals
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I'm Alyssa Ostroff — designer and brand strategist. Open to senior design and creative lead roles at mission-driven teams, and taking two freelance projects this quarter.

© 2026 The Nine Five Four, LLC, dba Alyssa Creative. Powered by caffeine. Lots and lots of caffeine.
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