I’m starting to think the reason her clothes are not tailored is because she doesn’t want to pay for it. When she was on suits, the stylist and tailoring was paid for by suits. Say she gets 5k spending allowance, instead of buying a 3k outfit and 2k on a stylist and tailoring, she just rather spend 5k on an outfit. This is the only logic I can come up with. Her ego tells her she can pull it off and make it work. Meg’s knows best always