The Freestyling World Of Pumpcat

[Curt]

I think its time to start documenting my outings. Maybe it will help others to feel comfortable enough to do the same. Yestarday was the fiirst time I went out in a skirt and heels. I've always wanted to do it and JeffB makes it look so easy. Anyway, I put on my fluevog hi-steady plat-pumps(4.5"chunky heel and 1.5"platform) they are a little pointy and have the look of old wooden dutch shoes. I call them my disco-dutch shoes. Google fluevog hi-steady pumps. I don't have enough time right now to post a pic. Grey opaque pantyhose, a kneelength danier leatherskirt in black, a womens white buttondown dress shirt and a wool peocoat on top. When I dress like this, I want the whole femme effect, so I styled my hair with a ton of volume and some subtle makeup(concealer,foundation and eyeliner on the outer lower lid). Lancome paris is my brand, no cheap covergirl or avon for me. It wouldn't matter anyway because I was wearing huge sunglasses. Something like victoria beckham would wear just to irritate people. I looked really good, almost too good. Pretty cool style for starbucks. The server said: what can I get you miss? I said: a grande vanilla creme and a chocolate chip cookie. Quite a lot fat grams for a size 0 model! Idont know why I waited so long to strut my stuff like this. I'm beyond the point about worrying about the perceptions of others. It was nice see what its like being on the other side for a while. I was totally passible. One thing I learned though, women hate it when other women look better than they do. Women just frown down upon other women when they can rock an outfit better or wear skyscraper heels with ease. What would they feel like is a guy could look better in womens clothes than them. Btw, I don't claim to be a woman, but dressed like that, I'm not exactly hanging out with my buddies watching baseball and knocking back gallons of beer! I think if you go out in a skirt, you have to do the whole nine yards. I got a few cat calls walking back to the car! I think my ego just doubled! Here's something interesting. I was in the car today going out to dinner. I saw a girl on the corner with really long hair, a peasant top, skinny jeans and the chunkiest platform sandals I've ever seen! I looked closely, it was a guy. I was shocked, tgen I looked at myself dressed like I could have no problem working as I hooker fulltime see, there are others out there. Living life to the fullest. Btw, I wouldn't go out full femme all the time. Only when thee outfit calls for it. I'm quite comfortable looking like a fashion forward male(whatever that means these days!). But I'm stuck with that gender idenity disorder that messes with my head sometimes. The only nice is that it makes shopping in the womens side of the store a piece of cake. Its just natural. I would have to say that 80% of my everyday clothes are womens. Aside from the heels, people can't tell the difference. Lately I think there is a smaller gap between mens and womens fashions. Everybody wears skinny jeans these days. I hope you guys enjoyed my outing. Ill keep them coming and of course fun and exciting. Feel free to post any comments you like. Ash.

[bluejay]

pumpat or Ash Great outing! I enjoyed reading your post. Keep it up. Happy Heeling, bluejay

[JeffB]

Hey there, pumpcat! Bravo to you for detailing that most interesting outing you enjoyed. It certainly made for entertaining reading. I'm glad that you considered me as being an inspiration when it comes to skirt wearing, admittedly, it wasn't easy at first, at least not in my own mind, but the more I wore skirts in public, with or without heels, the easier, and more fun it became. I hope to read more of your exploits in the future!

[Thighbootguy]

Ash; As BlueJay said, “Great Outing”. Size 0… sheesh, that must make getting the look you want easier. Being addressed as Miss, and catcalls do go a way to boosting the ego. I only recall being addresses as Mam one time then then the guy quickly realized his mistake. Do enjoy your look but don’t become complacent when you present it. It still upsets some folks, especially if they are mistaken in thinking you are a gal. I have enjoyed reading your earlier post and I’m looking forward to reading this thread. TBG

[Shafted]

I found is interesting that the girl with long hair turned out to be a guy.

[Bundy999]

Bravo!

[Curt]

I went out today in my fluevog Arresto boots over skinny jeans. There is something sexy about the name arresto, maybe a bit sleazy! Anyway, I went out to dinner to the usual restaurant I go to, no big deal! They know I'm a fashionista. Then to starbucks and walk around the mall and to the grocery store. I look more rockstar than anything else. It took a while to get used to showing off the whole heel, now I'm showing off the whole boot. Maybe this will inspire other fashion cats to do the same. Bttw, not one negative comment at all on my last two outings, but a lot of looks. Mostly this time because it is a guy wearing girls boots on. The first outing, they probably thought I was a girl and thought nothing of it! It nice to switch things around from time to time. My wardrobe consists of at least 90% womens and 10% mens. I've got everything covered except for what tops to wear. Obviously to look tasteful, not like I want to make a living on my back! What kind of top would you guys recemmend to go with skinny jeans and heels. Ill post some pics this weekend, ill have time because I don't have to work, but I have a leather coat that I have to work on. That's all for now.

[Shafted]

Boots over skinny jeans, I think you are discovering a very cool and comfortable way for a guy to dress. The comfort of skinny jeans is addictive, and when paired with knee high high heel boots it is just awesome.

[JeffB]

Boots over skinny jeans, I think you are discovering a very cool and comfortable way for a guy to dress. The comfort of skinny jeans is addictive, and when paired with knee high high heel boots it is just awesome.

Couldn't agree more. It's a stylish and terrific look that works exceptionally well.

[Thighbootguy]

JeffB and Shafted are right on. I'm sitting in a hospital room (as a visitor) wearing black fabric knee high boots with 3 1/2" block heel over skinny jeans. I think it's a great look. These boots are also great over leggings. TBG

[Curt]

I'm having trouble posting my pics with my blackberry. Ill post some this weekend from a friends computer. I have a ton with kneehigh boots, over skinny jeans, hose and various pumps.

[mlroseplant]

I've got everything covered except for what tops to wear. Obviously to look tasteful, not like I want to make a living on my back! What kind of top would you guys recemmend to go with skinny jeans and heels.

I'm thinking exactly the same thing. So now that I'm wearing heels and skinny jeans, or at least tight bootcut jeans, I'm thinking the work t-shirts probably have to go. But what to replace them with?

[Shafted]

I'm thinking exactly the same thing. So now that I'm wearing heels and skinny jeans, or at least tight bootcut jeans, I'm thinking the work t-shirts probably have to go. But what to replace them with?

I do tee's with skinny jeans and heels all the time. Just make sure there is not a lot of extra material in them. You don't want it tight though unless you have a killer body.

[KrisSullivan]

Pumpcat. Please post where you go in Toronto. It would be nice to let other heelers in town know where you have been without a problem of any kind. For me, if you have broken the ice in a particular Starbucks, I'll be sure to visit. Thanks. Kris

[Curt]

Pumpcat.

Please post where you go in Toronto. It would be nice to let other heelers in town know where you have been without a problem of any kind. For me, if you have broken the ice in a particular Starbucks, I'll be sure to visit. Thanks.

Kris

try jean machine, le chateau and other stores in eaton centre. But I've been everywhere in toronto in 4"+ heels. No big deal. I've gone out to dinner myself to the old spighetti factory with kneehigh boots over skinny jeans with a tight leather coat and a ton of mascara and eyeliner on. No big deal. dress the way you want to, no exceptions. Boots over pants are the only way to go. The only time I don't is when the boot shafts are just too tight to do over pants. The only look I don't really like is hose and skirts. Maybe I just have to get used to is. Others here did it, so I just tried. What I do is: look in the mirror before I go out. If I feel I look good, then that's the way I go out. If others like it, then cool, if they hate it, then that's out of my control. I'm dressing the way I like, not to show up others.

But to answer your question, I've been every where downtown from bloor and bay(prada, gucci, davids, holt renfrew) to the bay(even got a makeup application done right in full view with everybody walking by. Thanks for the girl that worked for estee lauder, just beautiful costemics) and everywhere on queen street from yonge to bathurst. Now all those areas are free for you guys to strut your stuff like the sex in the city girls. Let me know how you fashionistas make out, even in your own cities.

Ashley.

[Booted]

Pumpcat, Great post. How was it going out for the first time in a skirt & heels? Do you plan on doing it more often? From your experience is it better try it dressed as a woman or as a man wearing women's clothes? Are there any pros and cons to either approach? Booted

[Curt]

Pumpcat,

Great post. How was it going out for the first time in a skirt & heels? Do you plan on doing it more often? From your experience is it better try it dressed as a woman or as a man wearing women's clothes? Are there any pros and cons to either approach?

Booted

I like a mixture of both genders. Just like my name. Ashley was a mans name a long time ago, and now it is a girls name completely.

You have to go out and wear whatever makes you comfortable. I like the tight flare pants and chunky heels with a goth like profile(lots of buckles and zippers, and all black). Not really crazy about the womens skirtsuits. But it looks good on women.

I wore chunky-plat heels to a funeral yesterday. Later I took my shoes off, and said, now I feel a lot shorter. My aunt said: high heels! I never even realised at all. back in the day, we called those frankenstein shoes. So funny!

And tonight, I wore my arresto kneehigh boots over skinny jeans to go get an oil change at canadian tire. No looksor anything. More looks when I went to starbucks. I'm to the point where looks don't bother me. I just start to laugh. Its fun to be different, isn't it?

One of my friends on this sits is going to try and post some of my pics to this thread. I'm having trouble posting them. So stay tuned and you'll see them soon. Can't wait to see what you guys think.

More adventures to come.

Ashley.

[Shafted]

It is fun to be different, Ash, especially if it's done with style and taste.

[Steve63130]

I have an acquaintance who's a younger guy named Ashley, so it's not just a girl's name. Steve

[Jimnj3]

I am going to try to post the photos Ashley had trouble with. He sent them to me and asked if I'd give a try so here goes. These are of Ashley's latest adventure.

[Thighbootguy]

Jimnj3 - Thanks for the extra effort of posting Ashley's pictrues. From having read Ashleys's posts, the appearance is about as I has imagined (a little taller than I had thought). I like the looks presented, especially the jeans and boots look. Have fun presenting it. TBG

[Curt]

Thanks again Jim for posting my pics for me. My favorite one is where I have the tall boots on and I'm looking straight ahead. Such a nice smile. Too bad I have to wear glasses though. I wear the arresto boots almost every day. Many of you guys encouraged me to do it. Too bad it took me so long to have the confidence to go out in public like this. I like the knee boots better than the calf boots. The calf boots make me look too skinny. I wore the arresto boots to the dealership to get an oil chance, and then to starbucks. I got a funny look from a father and son. I almost started laughing. They were probably thinking: he doesn't give a damn what anyone else thinks. My rule is: dress the way you want to, no exceptions! Stafted goes to work in stiletto boots, JeffB runs around in philly in skirts and pumps, so there is no reason I can't strut all around the GTA area(greater toronto area) in knee high boots and skinny jeans. I've made a ton of progress, 2 years ago, I wouldn't go outside in 3" heels completely covered with flare pants. Now I'm rocking knee high boots, girls pants and coats, with cool hair mascara, and eyeliner. It might sound a little extreme, but this is how I like to look, I feel like I'm not hiding behind anything anymore. True happiness! More photos to come, feel free to give me some fashion ideas, and ill try them out and see how it looks. Hopefully I've inspired others as well. Ashley.

[bluejay]

Nice pics of you pumpcat. I especially like the look of your boots with your skirt in the last pic posted. Thanks for the pics. And thanks to Jimnj3 for your help in posting. Happy Heeling, bluejay

[Shafted]

I am going to try to post the photos Ashley had trouble with. He sent them to me and asked if I'd give a try so here goes. These are of Ashley's latest adventure.

Thanks for helping out, Jim!

Ashley, you definitely have the build for the retro/trendy styles you wear. Lookin' good.

[Curt]

I wore heeled boots all weekend at my parents house. They don't like it, but they know I like to dress in a certain way. They are probably used to it by now. My mom used to ask me why I wear heels all the time, I said because I like them, mostly the sexyness if them, and also because I don't have any flat shoes besides running shoes. Wear only running shoes If you are running. But I would rather wear kneeboots than pumps, because I have very narrow heels, and they pop right out of pumps. If I had any kind of fetish, high boots would be it. I like my boots with a lot going on with them. Zippers, buckles, straps. I've always liked the goth look with my boots. I might have to dye my hair black! No thanks, I've damaged it enough with flat ironing and blonde highlights. One of my friends wants a oair of boots similar to indiana jones(the movie) I don't remember what they look like. Probably some king of calf boot over pants. Wouldn't look too bad I guess.

[JeffB]

Well done on the pictures. You looked quite good there, pumpcat!

[Curt]

Thanks! My skirt was too short to see with the long coat on. Glad you liked it!

[Impala]

Keep on smiling, ash! You look so much better with a smile on your face!

[Curt]

Keep on smiling, ash! You look so much better with a smile on your face!

thanks! Ill keep the pics coming. And the smiles too.

[hhboots]

All really nice outfits Ashley... I am sure it helps having a slender body. I know that I would definitely push the boundaries a lot further if I felt I could pull it off. I am just not in the shape I would like to be at this time, and that makes it harder to enjoy more feminine fashions comfortably.