It would be easier for f2m to buy clothes than for m2f. One disadvantage is men's clothes are not so much diverse and noticeable.
Many working women wear like men in modern societies. Here in my country, some women wear those clothes like military uniforms, and indeed they are very aggressive and masculine. Those aged women are called 'ahjumma' here. Some stereotypes on ahjumma are poor driving, verbal attack, indifference to beauty, lack of estrogen, and extreme viability. We jokingly say there are three genders here: men, women, and the third gender, ahjumma.
Barbie~~