It took me a long time after realizing I was trans to transition, so I ended up having to get comfortable in women's sections while still looking very obviously like a man.
Turns out, it's the nervousness that makes people uncomfortable, because there's a lot of less good reasons a male appearing person might be nervous in a women's section. Once you can manage to shop with confidence, the worst anybody will assume is that you're shopping for a gift for a girlfriend or sister or something.
My girlfriend pretty much shoved me into the fitting rooms the first time I went to buy a skirt... I was so very nervous showing the gal on the door the one item to try on.
Fast forward a bit and I had a lovely experience at the Levi store ... was looking for a new pair of jeans for a holiday. As I was looking at the various cuts I was unsure wear to pick up, as I wanted something more form fitting. My partner said that the female cut has very little crotch area though, so potentially an issue there... so was looking in the men's section.
Assistant in the store came over and offered help. I somewhat shyly mentioned that I was looking for someone a little tighter on the skin, and mentioned "I have a masc pair already" ... their eyes pretty much lit up "Well you won't find what you want on this side of the store" and pretty much dragged me over to the women's section, and started pulling bits off the shelf and holding them up to me.
"Well this is pretty much the equivalent of a mens 34 waist, what do you wear normally?"
"Well my femme size in my clothing is usually a 16..."
Again a slight grin... before rushing me over to the cubicles to try on the items they picked out...
A very good eye they had... picked out a pair so comfy and I felt really good in. Was also just such an affirming experience.
A two-panel comic by BrookeValley.
In the first panel, a caption states "Me in the women's section one year ago", and a masc-presenting Brooke thinks "Are people looking at me? Am I making people feel uncomfortable?? [the last word is in italics]". (In the purple background, a pink t-shirt is hung on the wall that states "Live Laugh Love".)
In the second panel, a caption states "Me in the women's section now", and a femme-presenting Brooke holds a purple shirt with the words "Head empty" on her hands while humming "Doo-da doo Da-doo da Doo doo doo" (In the orange brackground, a pair of jeans are hung on the wall.)