My SO and I belong to a rather large MtF TG support group that has both TS and CD members. (Side note - FtMs are welcome, but no FtM has ever attended). Anyway, I've noticed that the CD members enjoy dressing up a lot more than the TSs, who dress pretty much like the GGs. The TSs have transitioned to female, and of course the GGs are already female, so we don't really need fancy clothes to feel feminine. We are feminine by virtue of being who we are. If this makes sense.
GGs and TSs do dress up once in a while too, when the occasion calls for it (i.e. weddings), but in our day and age, most of the places we go to on a daily basis are very casual. I rarely see anyone dressed up in our local restaurants, at the grocery store, at the mall, bank, etc, even at work ... and this goes for both women AND men. And I think a lot of people feel silly dressing up when no one else is dressed up, or at least I do. I hate walking into the room dressed to the nines when everyone else is casually dressed.
It's a lot easier if you have long lower lashes! I just smear the tip of the brush on mine back and forth, very lightly, and use my thumb and index finger to squeeze out clumps from my lower lashes if there are any. But if you dab the tip of the mascara brush on a tissue first, you won't get clumps.