Including a celebrity artist such as Grayson Perry in The Big Issue seems very fitting as he's publicly known for his contemporary art that aims to dissect British 'prejudices, fashions and foibles', henceforth allowing him to generously slot in with the magazine's anti-establishment ideologies as his lack of adherence to 'societal norms' is an evident, expressive political statement.
The eccentricity of his clothing in this article combats a contemporary conceived ideal of beauty and fashion; the lack of glamour, yet distinct tackiness alludes to The Big Issue actively rejecingt superficiality, and those who may try and make fashion statements out of 'hobo chic'. The Big Issue seems to pursue those who can boldly make statements of their own volition, and perhaps also will represent those who are more vulnerable in society.
Much like his art, Perry's outfit has a rather classical form, and is decorated in bright colours, that have been muted; this depicts a sense of being at odds with appearance, and how what we do is who we are, not our situation. By extent, this mirrors The Big Issue's ethos of being active in your approach to getting out of poverty and sometimes having subvert societal expectations by defying the stereotype of laziness surrounding homelessness and poverty by having to take on these supernumery roles in your life to get yourself out of hard times.
The celebration of the arts and culture here is evident, and is integral to The Big Issue's motifs as there seems to be a strong focus on the more expressionistic professions or interests, demonstrating that it's okay for people not to be interested in stem subject occupations, and that culture is as important to society.
The triviality between these two statements allude to how these eccentricities of character shoudl be celebrated as equal to other parts of our lives, not something to be ashamed of and hide. This may also reference the modern perceptions of gender, and the cultural shift to a more gender-neutral stance on topics, which means whilst the phrase 'textbook dad' in this contet seems a little more comical, it also allows the audience to gauge with gender ideals and expectations, and question what the modern day definition of such a parent would be.
The article name 'Letters To My Younger Self' suggests a sort of diary-esque entry, which would typically be percieved as feminine