Well a good tailor constructs in a bit of what they call 'lunch room' but its a good idea to get your weight stable. For health alone.
When I'm at home I tend to wear skirts and hoodies, and at work its all Dickies, Carhart and the like.
And while I'm on the subject, I hate, and like HATE, cubicle clowns in work clothes. I'm sure its the ever so prole look, but if your 'work' clothes don't show any of the markings of real work on them, you just look like a dork. At least go out and roll around in some gravel and oil and try to make it look like you live on a farm or do construction, or work with machines. Just my thought.
Though to your good taste, I don't see any of that going on here.