Before HRT and all, back in the days of short hair, I pushed my luck more with grooming than clothing.
Meaning nicely arched eyebrows, female glasses, foundation, a touch of coloured gloss, woman's watch, jewelry on occasion (bracelets, pendants, rings, etc.). Plus I stripped all the hair (what there was) off my arms.
No one ever said a thing, though I'll admit it's not the same as showing up in a skirt

For clothing, I did my best to find feminine-looking male clothing.. soft fabrics, nice colours, and so on.
Even now, five months into HRT, I'm in the super-fun "what IS it?" phase where some people see me as female, and most (I guess?) as male. I wear women's clothing entirely now, though it's fairly toned down. I guess people who see me as male just view it as male clothing, and vice versa. I haven't noticed any bizarre looks, though again, we're talking women's jeans or khakis, and nice sweaters and knit tops... not skirts and heels, so... maybe not a fair test.
Kate