is this a how? or Reasons for dressing to impressing?

Don't tell me that you don't dress to impress...

My gay male friends, professional associates and I share a common denominator in dress. We dress like gentlemen. This will hold with interviewing with a social worker. You are projecting a readiness to seek gainfull employment in appropriate attire.
For funerals, unless of distinct ethnicity with equally distinct customs, one dresses in somber colours of black or charcoal grey, perhaps a white linen pocketsquare and no display of ostentatiousness in cufflinks, tie etc. In point, if it draws any attention it is not appropriate.
As for your 'boytoy' scenario, since you have in effect self cuckolded  your masculinity it hardly matters.