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Well, I can certainly relate to what has been written so far. My "interest" in women's boots began when I was a kid, much before puberty...So, I guess I am wondering how I could have developed what might be referred to as a fetish before I had even developed sexually. I too, have spent/wasted so much time and emotional energy trying to "figure this out". I should try harder trying to find written material on the subject written by those with psychological knowledge on these things. I guess your best explanation is the simplest one, much like you have written.... You like the way you look in heels/boots You like the way heels/boots make you feel about yourself You think high heel boots look great These same explanations could be applied to why we make several purchases, such as cars, homes, jeans, sneaks, glasses, etc. I guess societal norms have been drilled into us so effectively, we make ourselves crazy trying to figure out why we would like to ignore what is "acceptable male clothing". I guess one big reason is that we question our "manhood" or sexual preference because we like to wear what society has labeled "female clothing/footwear". Being a member of this website has shown me a very important lesson, many different types of men enjoy wearing heels. There is no direct correlation between guys who enjoy wearing heels and sexual preference. The way I see it, a guy who has the guts/confidence to wear the heels he likes publicly is truly masculine and confident man indeed.

Those look just like my Ralph Lauren boots that I like so much, what brand are they?

Sefir Welcome buddy, glad to have you here....Those Amazon boots look great buddy! The question is: how well can you walk in them? Please do not attempt any public heeling in heels you can not walk smoothly/relatively confidently in. Stumbling, or being outwardly nervous in public can be a big set back when it comes to public heeling. Trust me, I DO understand, we all really want to jump out into public and show off our killer 5" heels. But, like all have said, the best approach is to start slowly in lower heels that you can walk reasonably well in. Starting off by fueling at night is a good idea. Throwing yourself out into a long walk in a heavily populated area is sure to create a lot of stress, you want to avoid emotional/physical set backs at all costs buddy. So, to answer your question, don't wear those heels to fuel up unless you can walk reasonably well in them... don

Mr. X Steve is right, horizontal stripes can be a disaster, but you have pulled it off fine with your nice long slender build....Loving the jacket, jeggings and boots also!

HOT boots you found there Cali!

I have a pair of thrift shop nine wests similar, but not as nice as, yours. Mine have zippers, and a little platform, total heel height is about 5". They are all leather and easy to walk in as well...

You are so right, just as so many here have said, confidence is the key....People are more likely to notice if you are uneasy, appear timid, or are unsteady on your heels. This is why it is so important for guys to take it slow and not get out publicly in heels they haven't mastered yet.

Joeshaw Well seeing this outfit is surely worth the wait buddy! The leather skirt, killer boots and great leggings are a home run for sure, nice legs as well!

Bootedlawyer Thanks for the info, Frye really makes nice boots. I remember being intensely intriqued by Frye campus boots when I was a kid, whether worn by guys or girls! I never had enough money to afford them when I was a kid, and had to settle for cheaper imitations. Now that I'm much older, I go through considerable effort to find all the vintage boots/sneaks/jeans that I wanted as a kid, but couldn't afford. I have a cool pair of vintage Frye campus boots with the 2" block heels, and really want a vintage pair of the tan colored Frye cowgirl boots the 3-4"heels. There is a pair of size 10s on ebay now, but Fryes tend to run small so I think I will be disappointed if I buy them. Last year I did find tan colored frye cowgirl booties in size 11, they look nice but prefer the taller shafts... Thanks for the encouragement! I'm in Atlanta today, will slip into my RL black stiletto boots and go for a walk. Tomorrow, will be in Vegas and was told there will be a pride celebration near the SLS hotel we will be at. I'm hoping to overcome an obstacle that has been holding me back a bit: wearing my boots over the levis...Pride should be a good chance to do just that....

Those boots are really made by Timberland, very cool indeed. The do look easy to walk in and have nice lugged soles, can't wait to see them on you...

Welcome bootedlawyer! You have achieved the look I am trying to achieve indeed. I love Frye boots also, but it is very frustrating not to be able to find them in larger sizes, where do you find yours? I wear women's US size 11s, it is rare to see Fryes in even size 10s. I did find one pair of nice Frye booties in 11s though. You look masculine and confident as a male in nice fitting jeans and great boots. You are so right. A guy who confidently mixes male and "female" fashions publicly is a fine example of confidence and masculinity. I really believe that most guys secretly desire to mix in some "female" fashions, they just don't have the guts to do it. In defense, most of us guys do not have that much power/control over our career/jobs, and they do have families to support. I truly admire your confidence, and wardrobe successes, you have got some great boots there. It's nice to have you here, and look forward to seeing and hearing more about your booted experiences. Don

Hope you had more fun than I did here in Phoenix! Climbed into my levis and black RL knee boots that I love and hit the streets after dinner. Not much going on around here when the sun goes down...Oh well, getting out and about felt good anyway, these boots are easy to walk in and I am getting to the point where I forget I am wearing them...A good thing for sure...

And I have some rough uses in mind for sure!

I'm from the US, so surely don't want to make generalizations about the UK...I am sad to admit that I feel wearing heels would hurt your chances for most jobs. But, on the other hand, for the less than 1% of employers who are looking for a creative/unique/confident applicant, heels might be just the thing to separate you from the usual crowd!