Anastasia Osindero

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Anastasia Osindero is a British entrepreneur. Anastasia started Boystrous in 2020.[1]

Anastasia Osindero, founder of BoystrousAnastasia Osindero, founder of Boystrous




@anastasiajade_ (1.01K followers)


@anastasiajade_ (1.05K followers)


Early Career

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Anastasia started Boystrous in 2020. They detail the beginnings of their company in their Starter Story interview: [1]

Q: How did you get started on Boystrous?

As an artist at heart, I’ve always loved the opportunity to create something. My interest in design was accelerated in the sixth form where I found myself sculpting and using light to paint shadows for various A-Level art installations. This is also where I had my first experience with Photoshop, using it to manipulate images for my year 12 art project.

I somehow went on to study Information Technology and in my placement year, ended up as a content creator for a start-up company. This is where I taught myself to do more than photo manipulation, and I learned how to make logos, flyers, and to illustrate and edit videos. Throughout my degree, I dabbled in modeling, fashion, and graphic design experimentation - freelancing as a graphic designer and remixing the clothes in my wardrobe when I couldn’t find anywhere to buy the clothes I had in my mind, or if I simply couldn’t afford it. My mother still yells at me for cutting up my clothes to turn them into something else to this day.

After my placement year, I decided that graphic design was what I wanted to pursue, but I was determined to finish my IT degree. Close to my finish in 2019, I thought about starting a modest clothing line for women. When I relayed this information to my partner and shared some of my ideas with him, he said “that sounds cool! I’d wear that if it was for men…”. It was a lightbulb moment!

There’s an undeniable gap in the market for a go-to store for men, in the same way, that women have PrettyLittleThing or Missguided, to name a few, and I knew the struggle my partner had in finding a store that was consistently his style preference. I then pondered over some name choices before ‘Boystrous’, a rebellious spelling of the word ‘boisterous’ came to mind.

As a graphic designer, it was easy to navigate from designing logos and flyers to creating patterns for t-shirts. I was able to test my designs on male and female friends around me to deduce the likeability of the garments. I had been working at Tesco during the lockdown of March 2020 a few weeks after I had gained the courage to register Boystrous. Before my temporary contract ended in late June, I had been able to invest in my business using my earnings, investing in a batch of plain t-shirts, a heat press machine, and a printer. This allowed me to create my first collection.

Source [1]