My outings...

[Cali]

@chesterx if you really want to go BOLD and I mean really BOLD try shorts with knee high stilettos boots. Look through Cali World and you will see that I have tons of pictures with shorts and different type of shoes.

I go to work in shorts most summers (except this one) and I always wear heels.  Wedges are always good with heels, but a nice block heel also go well. See picture below, Steve Madden Manners.  Be careful not to burn your legs, especially the inner thighs; those haven't seen the sun for years. And I hope they used serum on your legs after the waxing. And you may even want to try the bronzer next time.  

[mlroseplant]

6 hours ago, chesterx said:

Tried something different for me when I went out to lunch today. Now that the redness from the waxing has subsided I decided to test the waters by wearing shorts & exposing my legs to daylight for the 1st time in years. Was a quick one as I got it to go. There were two young ladies waiting for their order as well, & one complimented my sandals & the other my nails. Had a nice chat until our orders arrived. I'm calling it a success. I wore a top from Long Tall Sally, shorts from Aeropostal, & mauve sandals from Universal Thread. I just wasn't sure how I looked with heels, so I played it safe with sandals. I was thinking of wearing my mid height heels with this outfit as a compromise. Heels are rare enough in my area as it is, but I can say I have never seen a woman wearing heels with shorts, so I was hesitant to do it. I know some of you guys are practitioners of heels & shorts, any thoughts on the matter?

Yeah, ah, basically wearing shorts with heels takes it to another level. I think it's because it would be a noticeable outfit even if a woman was wearing it, even without a midriff-baring tank top or whatever. I do occasionally see a woman in high heels and shorts, but like RonC says, it's usually wedges, and I think in general, it's a waning trend. It seems like I saw it a lot more just a few years ago. It may be that if you went to bars and clubs, you'd see it frequently. I wouldn't know. I personally love the combination, and have ever since Catherine Bach of "The Dukes of Hazzard" made it her signature look. It really took about 30 years for this look to become generally accepted, however. I do this pretty much every day in the summer, and I still sometimes get negative reactions. I also get positive ones, too. I think you've gotten it pretty much right. If you want to add heels, be prepared to get significantly more attention that you would with either shorts and flats, or long pants and heels.

[bluejay]

chesterx, that's a fine look. I often wear shorts with heels, especially this summer as it's been record heat here in July. I always wear women's shorts as the fit and look are so much better than men's shorts. They usually run shorter, so more of my legs are showing. Mostly I'm wearing some type of heeled sandals, but I have gone out with pumps on occasion  and maybe a time or two in flats.

Happy Heeling,

bluejay

[jeremy1986]

On 8/5/2020 at 8:50 PM, chesterx said:

Tried something different for me when I went out to lunch today. Now that the redness from the waxing has subsided I decided to test the waters by wearing shorts & exposing my legs to daylight for the 1st time in years. Was a quick one as I got it to go. There were two young ladies waiting for their order as well, & one complimented my sandals & the other my nails. Had a nice chat until our orders arrived. I'm calling it a success. I wore a top from Long Tall Sally, shorts from Aeropostal, & mauve sandals from Universal Thread. I just wasn't sure how I looked with heels, so I played it safe with sandals. I was thinking of wearing my mid height heels with this outfit as a compromise. Heels are rare enough in my area as it is, but I can say I have never seen a woman wearing heels with shorts, so I was hesitant to do it. I know some of you guys are practitioners of heels & shorts, any thoughts on the matter?

I think you made a good call with the flats. Looks very natural. Well done. 

[chesterx]

A 1st for me today. Went to pick up my lunch from a cafe I frequent that makes a particularly nice eggplant burger.  Outfit similar to my last one with flats as I was just going there and back, no side stops. Cashier actually said she was disappointed that I wasn't wearing heels!

[Cali]

7 minutes ago, chesterx said:

A 1st for me today. Went to pick up my lunch from a cafe I frequent that makes a particularly nice eggplant burger.  Outfit similar to my last one with flats as I was just going there and back, no side stops. Cashier actually said she was disappointed that I wasn't wearing heels!

It's a common theme with me.  Get use to it.  

[jeremy1986]

2 hours ago, Cali said:

It's a common theme with me.  Get use to it.  

I knew you would chime in on this  Cali

[mlroseplant]

2 hours ago, chesterx said:

A 1st for me today. Went to pick up my lunch from a cafe I frequent that makes a particularly nice eggplant burger.  Outfit similar to my last one with flats as I was just going there and back, no side stops. Cashier actually said she was disappointed that I wasn't wearing heels!

 

2 hours ago, Cali said:

It's a common theme with me.  Get use to it.  

Yup, I've had the same comment before, as well. I cannot imagine the uproar it would cause at my dentist's office if I ever showed up in flats.

Edited August 10, 2020 by mlroseplant
Spelling

[maninboots]

On 8/10/2020 at 8:10 PM, chesterx said:

A 1st for me today. Went to pick up my lunch from a cafe I frequent that makes a particularly nice eggplant burger.  Outfit similar to my last one with flats as I was just going there and back, no side stops. Cashier actually said she was disappointed that I wasn't wearing heels!

I’ve had the same thing happen in Costa on the odd occasion I’ve popped in without my boots on, think they just come to expect that i wear them all the time 

[chesterx]

Hey folks, been kinda slow lately on the heel front. Having to transition to a new contract at work with a stupid fast completion date, so lots of overtime in the future. I make a lot of money but I'm generally too tired to mince about in heels when the week is done. This past Wednesday they made us return to the office, and our group will get Fridays as work from home day for the next 4 weeks. Me being the dunderhead I am I left my laptops power cord at work on Thursday, so I ended up going in anyway. I made the best of it knowing the floor would be mostly empty by wearing my trusty old American Eagle flats with the bow on it. Just a handful of people around so it was no problem. 1st two days were aggravating as the women picked up right where they left off by wearing some wonderful heels. A couple were sporting what looked like 4 1/2" stilettos. I get so jealous of them! I will have to persevere as best I can. One guy in my group did comment about the pierced ears, but it transformed into a conversation about tattoos. And one lady at the IT desk commented about my nails. No big deal I guess. Didn't have a lot planned for the weekend as most of the businesses are still opening up, but I did have one appointment that turned out to be fantastic experience. See, there is this little wig shop I have wanted to visit for quite some time, but the shutdown came. I popped in last Saturday, but they are only seeing clients with an appointment, so I made one for today. Turns out she is one of those gregarious types that are so fun to be around. I showed her a picture of a cheap wig I had years ago that I wanted to replace. She said she had something even better & returned from the back room. OMG, it was gorgeous. Just past Shoulder length brown that matched my natural shade with streaks of highlights throughout.  I am a fan of wispy bangs & asked if she could get it that way and to my delight she said she could style this one that way. She took it to the back & a few minutes later it was ready, & perfect. When she slipped it on me I knew I had to have it, but tried to contain my excitement until I made my offer of a slightly used mule & 3 chickens, but the best she would go was 15% off. I had her order another the same style that has longer hair so she can put it into a french braid for me. I found another style while browsing that was super cute as well. It is a short bob style that has that slanted cut from the back to the front with tons of layering, giving it a playfully tussled look from the side & back. She order one in the same shade as my other two. The best part was the fitting & styling. I always wanted to do the hair salon bit, but father time has seen fit to rob me of that opportunity, but this was fun taste of that experience.  She had so many wonderful tips & thoughts on styles, she has been doing this for 30 years and had some great stories to tell. Then as we were waiting for my card information to go though the balky card reader a couple of ladies walked in & we had a lovely conversation about Mediterranean cuisine. What a wonderful experience that turned out to be! I don't have much desire about makeup, but I may look into doing one of those makeover things just to see if it is as fun as this visit was. The impetus for the wigs was that some of the outfits I want to wear are a bit girly, & it seems I should make some effort to complete the look. I'm still thinking about how far I should go. So after that was sadly over I still had one stop to make at Bust Buy to get a keyboard, as I don't like the one on my laptop. In & out of there with no issues then my normal grocery stop, then home. For today's outing I wore my Nude stilettos from Nine West, my lace top blouse from long tall sally & my bling jeans from sexy couture. I wore these before so I am not posting a pic of them. The outfit I am posting I wore last weekend with a top I really like. It has arm openings that are cute & its really cool in this heat. It's by the humorous name of Cupcakes and Cashmere. My jeans were by Cover Girl, & the nude wedge heels were from Macys. I wore it for a haircut & grocery shopping. That's all for now...(definitely need to get my arms wax at my next salon visit).

 

Edited August 23, 2020 by chesterx
typo

[Cali]

Warning: Makeup can be a rabbit hole you can easily fall into.  I have had it applied for a Halloween outfit by professionals and I have learned how to apply it myself. I have learned how to do my eyes including "wings" by watching YouTube and experimenting. Even though I love eye makeup, I rarely do it. I more likely to just have light eye shadow and that's all.  One day it will common place for men, like it was in Egypt during the time of pharaohs. 

As you expand your waxing, look into multi-waxing packages. It will save you money. I have two, one for my legs and one for my eyes/brows. I take a drug whose side effect is fast growing extra long hair around my eyes that affects my vision. I had my eyes/brows last done in March, and have had to cut them myself 3 times since. Can't wait for our waxing salons to open.

Edited August 23, 2020 by Cali

[chesterx]

Crossed the Rubicon today, I suppose, as one of my wigs arrived. Still have some work to do, but having to wear a mask helps, lol. Plan to get my arms waxed next weekend. Not sure where I'm going with this, but my focus is still on heels. Went grocery shopping, & no one seemed to really care. Got two compliments on my nails, one from the butcher of all people. After that, went home, as I was still a bit nervous. Plan to take a nice nap this afternoon...Wore my Macy's mid heel print pumps, jeans from Long Tall Sally, & a top from Amazon...

[Kjones92]

9 hours ago, chesterx said:

Crossed the Rubicon today, I suppose, as one of my wigs arrived. Still have some work to do, but having to wear a mask helps, lol. Plan to get my arms waxed next weekend. Not sure where I'm going with this, but my focus is still on heels. Went grocery shopping, & no one seemed to really care. Got two compliments on my nails, one from the butcher of all people. After that, went home, as I was still a bit nervous. Plan to take a nice nap this afternoon...Wore my Macy's mid heel print pumps, jeans from Long Tall Sally, & a top from Amazon...

Is this progress within the past 12 months or year from when you first outed in flat shoes?

 Personally I've had to slow things down as I felt was going a bit too fast, I did stop again for a while until a month ago,  my confidence never really went and have continued with daytime outings since, but im still on edge about getting caught by someone I know. In addition to shoes, I've outed with skinny jeans several times, pedicure, hose/tights a few times and a skirt/hose once at night and a handbag twice a few months ago, shaved my legs. Wasn't sure were I was going with it ether and it was a bit too much withing my first few months, so I had to take a step  back to reflect.

Sticking to flats/low heels, skinny jeans for now, but I want  to make a couple of new milestones in September ( e.g. clothes/shoe shopping in person, may get my ears done), before the cold weather comes back and a possible second lockdown. 

Edited August 30, 2020 by Kjones92

[jeremy1986]

Well done @chesterx

Nice outfit and cute shoes 

[chesterx]

18 hours ago, Kjones92 said:

Is this progress within the past 12 months or year from when you first outed in flat shoes?

This is fairly recent. I had some interest in full cross dressing years ago, say my late teens & early 20's, but it faded over time. The only passion that has persevered has been my love of heels. I guess I should blame / thank Jeff, as I follow his jaunts with admiration, he has been an inspiration. It has stoked the fire, so to speak, & rekindled my interest in most things feminine.It also stoked some of the thrill that has worn off now that I am comfortable wearing heels at pretty much any time...

[chesterx]

Had an appointment with my estate planner  today, wasn't long, but I made the most of it. I was working from home today so I had time to dress up a bit. Got a classic double take from the receptionist! My attorney & all the witnesses & notary were good sports about it. I had a fun time, felt very comfortable the whole time. I am glad the public isn't so weirded out by things like this like it used to be years ago. Got many compliments on this outfit. It's a top & skirt I got from Ann Taylor. I thought my nude Nine West pumps were a good fit. Also considered my red strappy heels from Daily Shoes I wore in an earlier picture, but I think I will save them for a more casual event with this outfit. Other than a rain storm it was a great time...

[Puffer]

On 9/4/2020 at 11:08 PM, chesterx said:

Had an appointment with my estate planner  today, wasn't long, but I made the most of it. I was working from home today so I had time to dress up a bit. Got a classic double take from the receptionist! My attorney & all the witnesses & notary were good sports about it. I had a fun time, felt very comfortable the whole time. I am glad the public isn't so weirded out by things like this like it used to be years ago. Got many compliments on this outfit. It's a top & skirt I got from Ann Taylor. I thought my nude Nine West pumps were a good fit. Also considered my red strappy heels from Daily Shoes I wore in an earlier picture, but I think I will save them for a more casual event with this outfit. Other than a rain storm it was a great time...

Nice outfit - but I'm not sure whether hairy arms go with that look!

[mlroseplant]

1 hour ago, Puffer said:

Nice outfit - but I'm not sure whether hairy arms go with that look!

@chesterx, yeah, I think it may be time to do something with those arms. My arms are in that same realm as far as hairiness goes, but I don't shave them. I just use the electric hair buzzer to get them down to about 1/8". When the hair grows to about 1/4", I'll hit them again. It's a lot less maintenance than shaving, and gives 80% of the effect. Unless of course, a study in contrasts is what you're going for. Then, by all means, do your thing. I refuse to shave my chest, and therefore any neckline below the collar bone will never be part of my wardrobe.

[RonC]

I give you much credit for going your own way.  Personally, I doubt I could ever be comfortable dressed like that unless I was actually doing the full cross thing with make-up, etc.  

[chesterx]

6 hours ago, mlroseplant said:

@chesterx, yeah, I think it may be time to do something with those arms. My arms are in that same realm as far as hairiness goes, but I don't shave them. I just use the electric hair buzzer to get them down to about 1/8". When the hair grows to about 1/4", I'll hit them again. It's a lot less maintenance than shaving, and gives 80% of the effect. Unless of course, a study in contrasts is what you're going for. Then, by all means, do your thing. I refuse to shave my chest, and therefore any neckline below the collar bone will never be part of my wardrobe.

I couldn't agree more, unfortunately I couldn't do anything about it as my salon appointment was the next day. I decided to just roll with it as it was a just for fun & a quick meeting with my estate planner, then back home. I had my arms waxed in addition to my legs (really looks nice now), & a small portion of my upper chest as no one wants to see a muskrat in a tank top...

1 hour ago, RonC said:

I give you much credit for going your own way.  Personally, I doubt I could ever be comfortable dressed like that unless I was actually doing the full cross thing with make-up, etc.  

I dont intend to go this far for most of my outings. Mostly when I have the time to put this much effort into it. I recon for special occasions & the like. But heels will always be a main component of my outfits, regardless of the occasion...

Edited September 6, 2020 by chesterx

[chesterx]

Working from home today when I was told not only was a wig I had ordered ready but a handbag was ready as well. I took the opportunity to dress up a bit as I wasn't too busy, so took a long lunch. 1st stop was the wig store where I had a nice chat with the owner & a couple of patrons. Got some nice tips. I love what she did to style this wig for me. It doesn't show, but the back is done in a french braid to my middle back with some strategically placed loose hair. Afterwards I went to the local mall to visit the Coach store & pick up my order. Its a small bag, cream colored with silver  studs spaced all over the flap. Had another lovely conversation with the sales folks, but I had to get back to work. Was shorter than I wanted it to be, but it was a fun outing just the same. Wore a pintuck slip dress from J.C. Penny & my favorite black pumps, my Calvin Klein 4 1/4" heels. I also got my arms taken care of. No more gorilla arms for me!

[Kjones92]

16 hours ago, chesterx said:

Working from home today when I was told not only was a wig I had ordered ready but a handbag was ready as well. I took the opportunity to dress up a bit as I wasn't too busy, so took a long lunch. 1st stop was the wig store where I had a nice chat with the owner & a couple of patrons. Got some nice tips. I love what she did to style this wig for me. It doesn't show, but the back is done in a french braid to my middle back with some strategically placed loose hair. Afterwards I went to the local mall to visit the Coach store & pick up my order. Its a small bag, cream colored with silver  studs spaced all over the flap. Had another lovely conversation with the sales folks, but I had to get back to work. Was shorter than I wanted it to be, but it was a fun outing just the same. Wore a pintuck slip dress from J.C. Penny & my favorite black pumps, my Calvin Klein 4 1/4" heels. I also got my arms taken care of. No more gorilla arms for me!

I think you can easily pass with a bit more make up, lol

[RonC]

I agree.  I think you could pull that off if desired.

[chesterx]

On 9/12/2020 at 9:15 AM, Kjones92 said:

I think you can easily pass with a bit more make up, lol

Heck no, this is just for fun. Putting on makeup is not fun in my book. Besides, living as a woman, I cant afford the cut in pay!

5 hours ago, RonC said:

I agree.  I think you could pull that off if desired.

Thanks. I have been too busy this weekend to post an update, but after work Friday I was still in a mood to go out, wore the shorter wig with white jeans & my Jessica Simpson patent nude heels, & went to the Outback Steakhouse down the road from me. I've never gotten so many compliments as I did that night. Seems every server in the place had to stop by & say something nice to me, whether it be compliments on my nails, my hair, or my heels. The manager stopped by, & even one of the bus boys complimented me. I suspect they got together in the back room & discussed how to handle me. My server said she got into an argument with one of the other servers as to who made my shoes, she thought they were Jessica Simpsons, I informed her that they were indeed. She said she had several pairs herself & a pair the same style as mine, just black. After all the attention, & 2 margaritas, I was feeling quite fine. As I was finishing up a family walked by, & a girl about 12 casually glanced at me then gave me the cutest double take, then walked right into the back of her mother who had stopped in front of her. I got such a kick out of that. Anyway, I enjoyed the evening very much & managed to find my way back home safely, as those drinks were really kicking in....

[chesterx]

Had one errand, pick up an order at JC Penney. Ended up doing a little browsing & ended up buying a couple of earrings that were on sale & a pair of feminine sunglasses, as my only intact pair are wrap around & don't work well with my outfits when out in the sun.  After that a stop in at Outback for dinner. Pretty uneventful, even at Outback, where I got tons of compliments last week, but they were very busy today. Was treated respectfully at both locations. I wore a sheath dress by Stetson from Pinto Ranch & a jeans Jacket from Cavenders, I got both of them delivered today, all were on sale so this entire outfit with the shoes included cost around $80. I like this look but I'm not sure what shoes go best with it. I ended up wearing some strappy black sandals from Torrid I got on Poshmark. Any suggestions would be welcomed.

[projectz]

Those sandals do look great with the skirt, something about the block heel and the ankle tie go well with the flow of the skirt, great pedi too!

[mlroseplant]

11 hours ago, chesterx said:

. I like this look but I'm not sure what shoes go best with it. I ended up wearing some strappy black sandals from Torrid I got on Poshmark. Any suggestions would be welcomed.

 

Haha, well you know what I would have worn. My BCBG Bonny beaded white mules. But that's probably just me.

[chesterx]

12 hours ago, mlroseplant said:

Haha, well you know what I would have worn. My BCBG Bonny beaded white mules. But that's probably just me.

That had not even occurred to me. I dont even have any mules at this point. I agree, that would have been a good choice. Years ago I had a pair made by Candies, but ditched them in a "purge". Think I need to add a pair to my wardrobe...

[mlroseplant]

8 hours ago, chesterx said:

That had not even occurred to me. I dont even have any mules at this point. I agree, that would have been a good choice. Years ago I had a pair made by Candies, but ditched them in a "purge". Think I need to add a pair to my wardrobe...

I would ABSOLUTELY approve of Candie's. Being as they have changed over the years, the closest I can find in style is a company called Kiara. I don't actually own any Kiara shoes, but they certainly have that style down.

Also, being who I am, it's so hard to imagine not having a pair of mules. What's that like? How do you even survive? 😆😆😆

Edited September 21, 2020 by mlroseplant

[bluejay]

I too liked the Candies mules from years past. I have several pairs of mules from Naturalizer, Aerosoles and Calvin Klein among others. Now that fall is here and too cold to wear my sandals, I get my closed toe mules out and enjoy my heeling, before the booties and boots come out later.

Happy Heeling,

bluejay