I’m born a woman and I feel equally silly with makeup on…although very occasionally i will wear SOME mascara and other tiny bits of almost-indisitnguishable makeup….but it makes me feel wierd.

I think that part of the reason is that whatever your gender, you are still a nerd. You aren’t transitioning into a normal female, but into a female nerd. Women who are computer programmers or other types of computer geeks often don’t wear a lot of makeup. Which might be why it feels inauthentic to your new personality.

Sally Hansen 24 Hour Lip Treatment in place of lipstick.

You should be able to do it all in a couple of minutes, while your coffee is heating up, as that is what it takes me if I am in a hurry. A bit more expense and trouble, but does look better from a distance than no makeup at all.

A lipstick in a neutral or nude shade would be useful for before meetings or going out and about and meeting people, when putting pigmented grease and wax on your lips is worth the sacrifice for the extra plus in appearance. Some people go for the lip gloss – makes your lips look nice but like lipstick doesn’t feel natural to me.

I don’t use mascara, as I always wind up looking like Alice Cooper (I always rub my eyes and it looks like I have two black eyes).

For “women who leave a larger footprint” – DesignerShoes.com (http://www.designershoes.com/designer/)

Also Payless Shoes (http://www.payless.com/). Though most of their shoes are cheap (I mean more affordable to value minded shoppers”) I do like and wear their “Service Sport Oxford with safeTstep Technology” shoes in to work, and I think they don’t look too bad. I work in a shop / garage environment, so nothing but safety type shoes are allowed.

Find a great Lipgloss and if you feel like it, mascara. Try one that’s not so sparkly and who’s colour is similar to your natural lip colour. Most women don’t wear a full face of makeup but lipgloss is always in thier purse.

P.S.
Get better shoes (a good sleek black boot should do). You can get away with a lot as a woman, shoes are non-negotiable.

Good luck!

Megan>> Interesting comment re the gloss… I do have to wear some sort of chapstick all the time now (dry lips – surgery complication?)… maybe I’ll try that!

As for shoes, I do have some nice ones – those yesterday were Tod’s loafers we got in Italy this summer — not nice? Also, hard to find super cool shoes in 13 (I’m 6ft 2in after all!) I have a couple pairs of shoes w/heels that the Nordy’s lady found for me… but I havent’ been brave enough to wear those to work yet (and the weather SUX here right now)

when and if you do decide to try makeup again, you can get good* results with nothing more than mascara and lip gloss or a sheer lipstick.

KP

*pretty/feminine without feeling artificial, painted, or overly made up