Katrina

Whether you go in girl mode or as a guy, please make sure your toenails look good. You don't have to polish them, but make sure they are trimmed and not yellow. With heels that cute and open-toe, you would look out of place if you had gnarly toes showing. And for the record, I wish I had the guts to do that at your age!

Those are cool! I love frenchy nails and I wish I had the guts to do it.

Try either Bass or Clark's. They both have loafer styles that "can" pass as men's shoes depending on the heel height. I've also found ones that are close enough to men's at Kohls.

What they said. I did that too before my SO told me I needed to put on a clear base coat. I'm still growing out the stained part.

I know what you mean. I am incredibly picky about the shoes I buy - mostly because I can't justify paying for something that doesn't get worn out of the house much (if at all) unless I REALLY love them. I've gone months without buying another pair of shoes just because I can't find something that I like.

I've often seriously considered wearing some heels when flying. My issues is that when I'm travelling for fun, my SO is with me and I don't think we wants the extra attention (she knows, btw). When I'm travelling alone, it's for work and I'm afraid that it will be the one time that the airline loses my luggage and I'll be stuck with what I'm wearing. Since I typically have to go in for whatever work stuff early in the morning and I typically fly late at night the night before, that doesn't leave much time for emergency shoe shopping. Of course I could carry an extra pair in carry on luggage, but shoes take a lot of room.

I wore a pair of boots that I bought at Bakers into a video store one day. The guy behind the counter made an extra effort to compliment me on them. I was otherwise in drab.

HBG, those look really good on you. I love the boots too!

Its funny. If you asked me last year, I would have said that I would only want to look like a woman. Reading this forum has made me think that while I know I'm a CDer, I also am in touch with my masculine side - I just like bending the rules. I think that I'd like the skirt thing in guy mode though. I don't know what I want. I want to wear what I feel like.

It depends. Once when I was out in a pair of spiky 4 inch heels (in guy mode), I didn't care what anybody thought of me. It was actually a rush trying to evoke some sort of reaction out of people. Other times, I want to wear what I feel like and don't really want any reaction. I usually feel bad when I chicken out though and put on more practical shoes before going out. Conversely, if I do go out, I tend to feel proud of myself for having the ba**s to violate society's norms.

I have several pairs of women's shoes that I wear on a regular basis. In fact, I don't remember the last time I wore any of the three pairs of men's shoes that I have other than projects around the house. I have several pairs of sneakers, loafers, and flip flops that I wear daily.

I just bought a cute pair of purple shoes at a Baker's. The sales ladies were very friendly and were giving me advice (I asked for it) as to what to wear with them. She said that she had the same pair in black and purple. I should probably get a job there so I can get a discount!

I like 'em. They look really good with the jeans. Happy heeling.

The question really should be re-written: Have you ever gone to work in "girly" shoes but otherwise dressed in all-male attire?

I suspect that some of the answers here are from CDs or TGs, not telling us that they are dressed en femme. There's nothing wrong with that, it's just that we're not getting the whole picture. I think there's a big difference in wearing girly shoes dressed as a women vs. wearing girly shoes and otherwise dressed as a man.

GWL

Well, I consider myself TG, but I'm no where near full time, so I spend most of the time in drab - hence girly shoes with otherwise male attire.

That depends on your definition of "girly". I wear women's shoes to work every day. Most of the time they are loafers. I do have a pair with about a 1.5" heel that are relatively girly, but not heels by any stretch of the imagination (here at least).

Newfie, that's a cool outfit (both of them). You would fit right in at a local mall in my area on a Friday night - all the kids are goth. Not too many in heels, but you never know.

I know this is blasphemy here, but I wear flip-flops to the pool. Why would I want to risk getting any cute/cool shoes wet/damaged???? Of course, the flip flops are at least slightly girly.

Congratulations???? I personally don't understand why anybody would want to do that...and this is coming from a CDer who LOVES heels and has worn them out in public on a bunch of occasions in drab. I do yoga which has dramatically increased my flexibility, so I'm going the opposite direction! I have no problem with you wearing high heels out every day all day long, but please, do what some others have suggested and take them off for bed and do some stretching. It gives you the option in case you find a really cute pair of flats!

In additon to SF in the USA, I would think that Provincetown, MA and Key West, FL would be decent places...although I haven't been to Key West...yet.

I love those! Those are soooo cute! I'm sure they would go with just about any pair of jeans.

I had to get something today at Nordstrom so I thought, what the heck...I'll go in my new heels. I took a different pair - much higher and spikier, put them on, and walked right into the store. Nobody really paid attention on the way in and the store was pretty empty. I made my purchase and started to walk out the door. A pair of women walked around a corner and heard/saw me in the heels but didn't have much reaction other than a quick smile. I turned around as I opened the door and saw one of them checking me (and my heels) out. She saw that I caught her looking. I gave her a quick knowing smile, then she smiled and turned around. I turned and headed out. It was fun! I didn't think I had the guts to go out in obviously women's shoes in public. To date, anytime I wear women's shoes out (all the time), they are either very andro, or I have on long pants that would cover them up. This (and yesterday) were the first times that my girly shoes were obvious.

These are what I wore today:

http://www.flickr.com/photos/7915625@N02/541244142/

http://www.flickr.com/photos/7915625@N02/541244150/

And I wore these yesterday (although my nails were painted yesterday - Frenchy):

http://www.flickr.com/photos/7915625@N02/541244164/

http://www.flickr.com/photos/7915625@N02/541244142/http://www.flickr.com/photos/7915625@N02/541244150/

For some reason, most of my shoes are black. I have a few brown, one grey, one purple, one red, and one pink. Oh and a while pair.

I've been out in heels before, but under long jeans so they didn't really show up at all. Well, that all changed today. I bought a pair of peep toed pumps today. I slipped them on and went shopping. I hit a Fashion Bug in a strip mall and a Macy's in a mall! What an amazing feeling wearing heels out in guy mode in public! I started walking around in Macy's to see if I was going to get any reaction from anybody...nothing. I did get a smile from one of the girls working at Fashion Bug...the type of smile that was just about to be a giggle. I know she saw them.

Congrats! And those boots are cool!

I've actually been on a shoe shopping binge recently. Two days ago I went to a store and tried on several pairs while other customers were around and the staff working there. BTW, it was a warehouse like place where you serve yourself. I would put the shoes on and march up and down the aisle to the nearest mirror to check them out. Some women gave me a second look, but most just ignored me and did their own shopping. Yesterday, I went shopping again at a different store. I've been to this store several times now and I think I had the same young guy at the checkout a few times now. I used to be really intimidated when I have to checkout with a guy doing it, but its starting to bother me less and less. He even came around the aisles to ask me if I needed any help. I'm pretty sure he saw me trying them on and didn't give me the hairy eyeball or anything. The truth is, most people don't care.