hhboots

I rarely dress up like this (and never in public), I'm mainly into just heels, but figured many others here have posted these kind of shots, so I might as well do a couple of my own while I had a chance. Yes, I know the sweater dress (borrowed from my wife) and the shoes don't really match and the shoes are not that pretty, but I had to take a photo like this once I suppose. Don't worry I don't plan on going out like this any time soon Be kind, it took a lot for me to post this...

Probably restating what many have said, but telling you what I have done. Start with some sensible and comfortable round toe, 3 inch block heel/wedge boots/shoes, and wear them under some long bootcut jeans. Do that your first several times at least and do it in an area where you are pretty sure you won't run into people you know the first times out. It has been a year now since my first outing, and I still am using that more discreet look under jeans quite often, usually with 4"+ stacked heels now. Many others here are quite a bit more adventurous and bold than I am, and thats great, but I want to be comfortable when doing this and not draw unnecessary attention to myself when I don't need to. Anyway, by far the very first step out is the hardest, once you get out there just keep on going and be confident, look like you belong and own the look.

but hey, I like 'em.

That's all that matters right? You like them, and you are having a heck of a good time in the process.

That is really cool Daniel, very impressive. Congrats

You sure live the life KH. Hanging out with models, and Milla Jovovich *drool* I just love that woman - You are the man Being married with kids, my version of streetheeling is nothing like yours and is nowhere near as exciting, but at least I can enjoy reading your adventures.

Today was one of those Autumn days that seem to be full of possibilities. I got lucky and got out of work a little early so I could enjoy it. ...

Another great adventure story. Those pants, wow! Those have some serious flare on the bottom, I imagined a bootcut at most, but those are some absolutely wide bottom pants there.

Well, keep on having fun with it, and sharing your adventures as well.

Welcome, I hope you enjoy your time here. Also, enjoy your new life in LA, that's a pretty significant change from Syracuse.

Its funny that #1. pair of shoes got so many granny comments in this thread. I had originally pictured a sexy pair of feet wearing those shoes and they looked just fine to me at first, but now that you all have mentioned it, all I can see now in them is granny feet. Ahh well

How very cool, TBG. The boots I wear on occasion at work are about 3-3.25" chunky heel and are barely noticeable as being heels under my jeans. I guess I am happy with that result. I suppose a good compliment on the look would be nice but I like to stay pretty far under the radar at work at least.

Last Sunday, getting ready to go visit some friends, I took off my fairly tight fitting straight leg women´s jeans that i had been wearing around the home and put on a pair of men´s jeans instead. My wife took one look and told me to change back again. She said the women´s jeans look much sexier on me. I was happy to do as i was told.

Nice Yes, men's jeans pretty much suck ... especially the designs in the last 5 years. It was getting harder each time I went to the store to get proper fitting mens jeans, with the "relaxed" this, "loose fitting" that, and generally baggy carpenter pants hanging everywhere ... screw that. Women's jeans are the ONLY jeans for me from now on.

I have seen women at my office wear open toe shoes, sandals, and boots, many with heels reaching 4" or so. I think all of the ones you linked are all pretty close to pushing the boundaries for many offices, but with perhaps some carefully selected conservative and professional clothes to match with them, I think they all could be acceptable at work.

Play some Wii and Xbox 360 stuff with the kids mainly. I have also been known to *occasionally* play a certain MMORPG computer game that I won't mention by name

Welcome Malc, we have a wide range of guys (and some gals) here, and we seem to all get along... well, most of the time Anyway, enjoy your stay.

Good answer William. Adding to that same question... I feel I have to dress more conservatively at work, I don't want to jeapordize a career I worked hard to have and since I have a family to support, I just feel its not appropriate to take those risks. I have tested some boundaries at work with women's jeans and a several times have worn androgynous looking 3" chunky heel round toe boots hidden under bootcut jeans. I feel pretty comfortable with that look, and know really no one notices. That is probably as far as I will go for work. Outside of work, I am nearly always wearing 4-5" heels that are quite a bit more obvious. Even in front of my kids, they seem used to the look and don't even ask me about it.

I too prefer knee boots for those reasons William, but ankle boots can be good too. Since I cover my boots with jeans anyway, I tend to use ankle boots more often for convenience when I go out and them not being as hot for longer periods of wearing them. The ones in his photo aren't exactly my style, but I won't go as far as William with the "negatory response". I think Bootking looks just fine.

Nice boots, I would have a hard time not buying those myself (but the price will keep me from doing so). Yes, buying heels is incredibly addicting, and difficult to keep under control. When I get the urge, I try tell myself, I have a pair almost exactly like them and try to get the mind on something else. Only when I find one that is completely different from the ones I own and the price is not too crazy, will I follow through. I agree, it is very hard to not buy new pairs every single month, I share your dilemma.

Yes, I ran into this myself recently, I was proud of some new clogs I recently got (my only pair of them, and I am usually not a clog/mule kind of guy), only to find out an hour later into wearing them that the pants get tucked in between the foot and shoe, fully exposing my secret, and was a bit embarassing The only solution I found that worked *mostly* was for sure no nylons to cling to, and make sure the pants went almost all the way to the floor, so they wouldn't be short enough to get tucked in. Audrey has a nice solution, but most of us guys are not ready to go that far yet.

I like those wedge shoes Daniel. My collection has just started growing considerably this year with the introduction of streetheeling into my life. About this time last year, I was at around 5 pairs of hh shoes/boots total, today I have about 30 pairs and it grows by 1-3 pair each month.

Have fun and be safe in the mountains, be sure to take some high heel hiking boots with you

Welcome back Scot, I am also looking forward to hearing more about your recent adventures. Wow, a day at Six Flags, in those sandals!! OMG

degrees

Pretty much exactly like the others have said, it all depends on the fit. If its looser fitting, then a thick sock, if its a very snug fit, then hose are the only way to go. A much nicer feel of hose/tights with boots by far, and I would never wear boots barefoot.

Absolutely no on the Rosa shoes. Those just look silly.

But then I seem to be lately drifting away from even the normal length, traditional pointy shoes. I really like a smoother rounded point such as these. In fact, that is about as pointy as I will go anymore.

Sounds like a great trip to the store, how cool. Well I am sure you will enjoy them, take it easy.

Hello Keith and welcome. Good intro ... and I agree that flats just don't feel as good as heels. Even in my few pairs of men's shoes, I wear insole lifts inside so I almost feel like I am still in my heels and its not for height or anything like that. I am about 5'11" barefoot. Just the angle of the foot and arch support feels right in heels.