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I wish I could provide concrete answers, or opinions to your questions...There are so many variables, especially the build and swagger of the man wearing the heels... Anyway, I would agree that bare feet or hose/tights are best for heels, no socks.. Some guys, especially tall men, with long legs and a swimmer's build, can pull off most looks effortlessly....Then, there is the rest of us guys, who don't quite fit into that category. So, all I can say here is that what might work fine for one man, can not look so good on another...Wish I could be more concrete, but there are hundreds of variables that affect the look... To me, most guys look better in jeans with heels, but that is just my opinion...In any event, the jeans must fit correctly, and be the proper length, or they can really detract for his appearance in heels..Like FF has said, very loose jeans that are too short are usually a no no... Seasons, hmmm. Oh well, I'm sure there are seasonable looks, I just wear my boots and jeans the same way all year... As for "no nos", again the variables are so many that it is hard to even generalize...Again, usually only slender tall guys can pull off extremely feminine looks successfully. So, the rest of us kind of need to be able to blend our heels with more masculine attire.

I'd like to see 30 contributors, full-stop. HHp takes a lot of interest, that might be more appropriate here. [Men in heels, and ONLY interested in wearing heels, not skirts and other feminine attire.] Traffic counts, so no surprise the draw is to a busier place? Plus there are a much larger number of female contributors there, and if there's one thing that's going to attract men interested in high heels, it's going to be a site where woman talk about/show their interest in heels. (Bees and honey-pot syndrome? ) Recently, H4M has been busier, but can the momentum be kept up? Many new (and older) members visit without contributing. Not sure why that is? If you have an interest in heels, you MUST have or see experiences of heels, on an almost daily basis. Not many reports about this though? I guess members believe their experiences would be of no interest? Can't see that myself, as I find entertainment in the most (seemingly) mundane encounter? ....

Wow, big question. I'd think 30 different opinions, from 30 different people? Here's my go anyway. My lifetime experience from living in the UK, suggests bare feet are the only fashionable way to wear sandals. That would be with a heel, or without. Mrs Freddy also tends to wear bare feet in boots too, but that's more to do with comfort than fashion. I have seen sheer hose [so no reinforced toe] worn with some open toe shoes, but this would have been to give a better colour to pale legs or block imperfections in skin tone. What doesn't work for me, is kitten heels on shorter, wider people. In fact I'd offer kitten heels only work with slim long legs. Higher heels seem to infer a slimming look on wider people, For men, trousers or jeans flapping around ankles with all of their heeled shoe on show, ought to be an arrestable offence. In fact the only time it works for women, is with collettes. [Very baggy ladies trouser. Often made of something fluid, like linen.] I'm a traditionalist. Sandals in the rain don't work for me. Anything sparkly. Stupidly high platforms. Very nice boots, attractive rise. I would never be brave enough to wear any calf/knee boot, over my trousers or jeans.