First of all, you may ask how I ended up in a fleece and baggy tracksuit bottoms with two kids (don't like that term, seems derogatory) in tow. The answer is partly the same as you might expect for most women in that situation: practicality, haste, lack of time to myself and the fact that I was a parent. There's more to it than that.
The kind of things I used to wear before I transitioned included often baggy and holey leggings, frequently stained hoodies (never pullover ones for some reason - I might explain that later if I ever find out), crop tops, and of course trackie bottoms and tops, even matching ones, oh and fleeces, sometimes with busted zips. I wouldn't be surprised if the pre-transition transwoman quite often wears clothing of that kind of genre, or rather, clothing which shares significant features with that lot, with the probable exception of the crop tops and leggings. This is for a very good reason: these items of clothing are to a considerable extent unisex. They do not signify gender. Naturally they may very well not include such items and if she uses a different and quite common coping mechanism you might be more likely to find her in a suit and tie or the uniform of a police officer or soldier. If on the other hand her coping mechanism is like mine, and I don't know how common that is because we all have our own stories, she may, as I did, attempt to wear clothing which does not in itself get commonly ascribed to a gender, because it's as far as she feels capable of going to avoid confronting her revulsion at the state of her body, and the repellent fact of having the wrong physical sex.
There is of course another element in this statement: "real" women do not usually wear ballgowns in the supermarket however much the proprietors might be working their way towards making them. The implication seems to be that that fabulous beast the transvestite is in a privileged position and lives in a fantasy world where they don't have to drag children round supermarkets. Of course male privilege is depressingly real, as is cisgender privilege, and many trans* people I'm sure have dual roles, one of which helps them cope with the other.
A random day in my life from 1999 to 2013 would probably have found me in a tracksuit. This used to irritate Sarada no end and she noted correctly that my hoarding of the garments constituted a problem. Towards the end of that period, I pointed out to her that the alternative would be me wearing clothes she would regard as feminine. To me, the way this looks is that I can wear what to me are normal clothes although with an obvious bias towards dresses, skirts, tights, blouses or whatever partly because I got sick of never wearing them, or I could camouflage my identity by wearing the likes of tracksuits. She was not aware of the implications and didn't realise what "normal" was for me.
Therefore, should you happen to see me and wonder why I'm dressed like a caricature of a ciswoman, remember that I'm not doing it because I think this is what women are supposed to look like but because the fact of my male physique makes me want to slash my wrists and a number of other things. It's not intended to be in any way an insult or a fetish, although as I've said there wouldn't be anything wrong with that if that was what this was about. It's just my way of coping, like the tracksuits used to be. It also seems pretty natural and ordinary to me and in fact I don't really get why people restrict their sartorial choices to only wearing so-called "menswear".