international women's day - work wear!

<3
Talked to a woman at work today and she normally wears the latter comfortable style - but she was dressed more like the first images with heels etc because she was going on a sales visit. 
And I wonder would a male dress up any smarter than normal for a sales visit or is it more of another work hassle for women - to look polished and slim and tall ( this girl was skimming 6 foot without her heels) 
And also as a bigger lady who would not be able to pull off that coture shape - do I look frumpy and unkempt even when I dress up with more effort than a colleague because people are expecting pictur one and not two when it comes to style in the office? Also is she selling her image or the company?