CAT

Was out Saturday afternoon and evening shopping.   I know this will be a huge shock to you guys,,,,,,,,,, I’m not in a skirt and heels!!!!  Can you believe it!   I have a men’s black shirt, a silver sleeveless Wolford bodysuit, Lululemon leggings, black boot socks and Sorel Joan of Arctic wedge ankle boots.  All great compliments on my outfit and boots everywhere I went!!

Welcome to HHP!    Looking forward to your posts.   Look around as everyone here has a lot to offer

CAT

Welcome to HHP.  looking forward to your contributions!     

CAT 

On 3/6/2018 at 8:17 PM, mickeyunc said:

here,s my try  whats everyone think

Looks great.  Love the white pumps!

Spectacular!!!!!!!!!   What brand are they ?

4 hours ago, KneeBooted said:

So with the leggings aspect, there is one main reason, and the decision to wait came after talking with a female friend who is aware of my heeling etc. While I have not posted any pictures or updates, I am in the middle of seriously trying to reshape my body. Since January 1, as all New Year's resolutions start, I am down 18 lbs and one pants size! My goal is 30 lbs and two pants sizes. I normally would wear a 12, am a tight 10, and hope to achieve some sort of an 8 when all is said and done. Because of this, even though they make stretch leggings, I want to be at my final goal/size before buying any more pants related items. I'm already a little bummed because a bunch of jeans and pants I recently bought off PoshMark are now starting to fit on the loose/too loose end and will inevitably be resold or donated.

So while nervousness plays a small part, the big part is my weight loss and reshaping!

Good for you!   That seems to be a hard thing to do even for me.   I really have to watch what I eat, well not watch it but cut back and cut out some things.   I have lost some weight but need to keep going.  Ideally I would like to get down A few pounds, like 10.    I have a ton of clothes in size 4 and 6 and want to keep it that way.   It’s not easy when I love to eat, good food and junk food,  wasn’t a problem when I was younger but it is now!!!!   Good luck on your quest I know it’s not easy. 

10 hours ago, balletboot said:

Here are a couple long overdue pictures of the last skirt i bought.

 Ive been real busy with a new job so i havnt had to much time to get out in heels :/

I have my first day off in a month coming up this week i am hoping to get out

 

That is an awesome skirt!

On 3/4/2018 at 2:03 AM, balletboot said:

 

Several awesome looks !!!

19 hours ago, KneeBooted said:

I'm curiously wanting to get into leggings... so sure!

Soooooo what are you waiting for?    I wear leggings almost every day.  At hone shopping working out running around grocery store    Usually with my Soren wedge ankle boots Michele Kors knees boots and  yes sometimes guys shoes and even gym shoes.   Mostly Lulu some Nike and Under Armour 

Awesome outing and an awesome pic!!!

Those are awesome!   I want a pair

I have some ankle many knee and a lot of thigh high boots.  A few 4” mostly 5-6 “ a couple of  7”.  

Mostly in thigh high boots and a mini skirt to go out on date night or to the city.   Ankle and knee boots with jeans, skinny jeans or leggings for just running around 

5 hours ago, Jkrenzer said:

Ok, now I'm curious, what kind of conference causes you to get glitter on your face?

Me too

5 hours ago, JeffB said:

Here’s a question worth pondering: is being overdressed a bad thing? When I embraced the unique lifestyle of the fashion freestyler, I made it a point to always, and I mean ALWAYS look my very best. I mean, if I was going to traipse out in public wearing women’s clothes AS A MAN, then I’d damn well better make sure I didn’t look foolish or inappropriate. Because of that particular mindset, I tend to think I overdo things, that I overdress. I want to look sharp, I want to look stylish, I want to look fashionable, but do I go overboard at times as a result? Perhaps.

Case in point: A few days ago on President’s Day, I went to the local casino to have a little fun and spend a little money, and while pretty much all the women there were in purely casual, even frumpy or sloppy clothes, there I was in a nice sweater, a pencil skirt, hosiery and heels, even for a place as innocuous as a slots parlor, I just couldn’t bring myself to dress down. Or on another occasion at the King of Prussia Mall, I sported my black leather jacket over a turtleneck, a dressy a-line knit midiskirt and high heeled knee boots, and I can assure you that NO other female, young or old was half as put together as I was, even though I didn’t need to be, but, I can’t help dressing up for outings like to the mall. I’ve said this a time or two or a dozen, and I believe it to the max: when I look good, I feel good, since wearing women’s clothes is great fun, I want to do it right. Perhaps vanity plays a part in my habit of overdressing because I like to show off, to display my fashion style since I look better in women’s clothes than I do men’s, something that’s also fun as I just love strutting about in a skirt and heels, it’s a highly intoxicating feeling.

To everyone reading this piece, regardless of your level of commitment to freestyling, if you wear just one article of clothing or go the whole hog like I do, it’s important that you take pride in your appearance when out in public. That you put a premium in being knowledgable about fashion and looking your very best, because you’re setting an example to the whole world for men who wear women’s clothing, and that example should be we CAN look tasteful and stylish in the clothes we choose to wear and not odd, freakish or embarrassing. I don’t mind admitting I obsess over looking my best, I never go out unless I am, so, if that results in being occasionally overdressed for the surroundings I happen to be in, I don’t mind that at all. If anything, I’m rather proud to say I overdress, like everything when it comes to freestyling, it’s a thrill. Opinions?

You are 100% right in my book Jeff!!!!    If your going to go out look good.  My GF stresses about looking good when she goes somewhere.  And it’s dressed appropriately for where you are going and what you are doing. If she is teaching Pilates she’s in lululemon and looks fantastic.  If we are shopping she is dressed up but not over dressed.  Dress and boots or heels.   Leggings and boots with a sweater.  If we are out on the town she is dressed up to be out on the town.  As for me,,,,,,,, well you have seen the pics of when we are out in the town.  She says I stresss and think about it more then she does   I have to it’s not that easy to look as good as she does with 1/2 the effort.  Also I keep my outfits, depending on the activity in check as she is the important one not me.  We are going out shopping first today and I am wearing a men’s lulu shirt lulu leggings boot socks with my new Sorel Dacie heeled boots.   I’m taking another outfit to change for dinner and drinks 

Jeff, you always look fab in your pics.   If your going to get dressed you might as well look good!!!

Go with the less noticeable boots. However, if you want to get noticed wear the stilettos I know I would and do.  

Also if you think you may get in trouble from your wife or others you might as well make it worth the trouble and wear the stilettos!!!!  LOL.  actually it’s not worth upsetting your wife over a pair of shoes.  I always put my family first when I think about where I am going to dress appropriately.   

CAT

We have been shooting for a Chicago gathering since last fall.   Let’s get this party started !

11 hours ago, spikesmike said:

HHMafia :  I just ordered a pair of Black Ankle Boots. $79.99. My first ever order from them . They say delivery with in 20 days. I will add up date when they arrive.

These are not the boots. I just like adding a little spice. Who can tell me where I can order a pair of these Oxfords ? Can not find the seller anywhere. 

I will take a pair tooooo!!

17 hours ago, Tacchi Alti said:

.. I just wish someone would comment on them! I might JUST be persuaded to wear stilettos if one of them dared me to wear them...

Ok I’ll do it ,,,,,,,  I dare you !!!!!!

lol

CAT

SoCalGal,

Glad you found us!   First off I will say I am another normal straight guy here,,,, well I think we are,,,,,, it’s everyone else around us here at HHP that aren’t normal!   I have been wearing heels in public for over 5 years now.  For me I like the look the feel and boy do I get better service at the stores, bars, clubs, restaurants, even Home Depot.  My GF is perfectly fine with my choice of clothing and heels, we shop together all the time.  Here are a couple of pics  I am not dressing to pass as a girl,  I am just a guy in a skirt and heels that’s all . No make up no wigs no boobs, period .  It’s always nice to nave a girl here to give us the female opinion  Hope you stick with us normal guys !!!!

On 2/17/2018 at 12:33 PM, Jkrenzer said:

Why wouldn't love heels. My old Pleaser two tones at work.

Absolutely fantastic way to dress at work!!!  I’m jealous! 

I think it would be good

23 hours ago, bnchmrk said:

Ordered these today. Found them on urbanplanet.ca on clearance. I am not usually into the lower block heel but I saw a woman wearing a similiar pair and liked the look. Thought maybe the top could be turned down and worn under a looser fitting jean. This could be my first step out into public with a rather inconspicuous heel depending on the heel coverage.

You should absolutely wear them out,,,,,,,,, with leggings or skinny jeans tucked inside!!!

Those heels are fantabulous !!!!!

22 hours ago, balletboot said:

I went back and bought the black and white skirt i was talking about. I went in wearing my supper skinny jeans plaid shirt and aldo heels.

The shirt im wearing doesnt go well with the skirt at all. But it went alot better with the jeans i wore into the store.. i also tried this other knee length skirt but didnt buy it as it was still $60

I would have bought both!!!!  They are both awesome.   Where are you shopping??? Express?    I always stop there 

On 08/01/2018 at 6:16 PM, spikesmike said:

Heelers : Purchasing several pair of Boots and Pumps at one time has its downfall. Do not remember if I have already posted these.

Isn’t that the truth!!!! Looks great anyway!!!!

On 10/01/2018 at 1:42 PM, chrigi-ch said:

last week an nice package just arrived at my postbox,

the content was wven nicer

heel: 18cm

plateau: 3cm

shoezise: EU43

Those look like they belong in my collection!   What brand are they?