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I hear ya for sure. But, I have found/noticed that a mix of subtle "feminine gear" along with decent "masculine gear" can be a great look indeed. Just a guy, happy to be a guy, wearing a touch of "feminine gear". I find this to be a very confident/powerful look indeed. Needless to say, many guys have nice long/lean/toned builds and look great in even more feminine gear, not a look I can pull off for sure... I recently bought a few pairs of women's nike leggings/work out gear pants from a thrift store, just to get a better idea of what size would work for me, and just how I would look. I enjoy wearing them, but afraid to see an actual picture of me...Afraid I might be "overstepping", writing checks my old dad bod just cant cash!

Between 85 and 100% of what I wear comes from the woman's side, but other than my heels, I don't look feminine. Even with gel fingernails. More colors and fabrics to play with, better fit.

This pretty much describes me too. I wear leggings a lot and while I have tried to buy better ones, the ones I like the most, and fit best for me are the $5 kind found at thrift stores. I have worn them for so many years that I don't even pay attention to them anymore. I don't wear them in public except for maybe mowing the lawn or working in my woodworking shop. In all the years I have been doing this I have only had issues twice. Once was when I was sitting on the couch and the wife took a picture of a woodworking coffee table I had made. I was out of the picture... I thought... but the reflection in a mirror showed me which my mother-in-law just said, "Mr. Crushed Vamp looks very relaxed"... The other issue has been... well... women in leggings SOMETIMES get Camel Toe, but being tight pants and male, let's just say sometimes I show "Missile Toe"! 🙂

I was walking along the towpath this afternoon, wearing low heeled knee boots and came upon one guy who was certainly staring. It was odd because around the boatyard and amongst the boaters everyone just expects me to be wearing boots - I always do - so it was unusual to see this guy with the puzzled expression. I said hi and he responded and we went our ways

I think the femininity of my boots in an otherwise masculine look - jeans and fuller- creates a nice frisson. It’s edgy. And satisfying. I think a natural sensitivity and awareness of stepping out of bounds makes us more critical of how we appear in heels etc. we hold ourselves to some heightened standard. A woman would not do that. Women come in all shapes and sizes, like we do, and they buy and wear feminine clothes matter of course.

I go back and forth with that a bit. Beyond the shoes, I wear women's pants, but they don't particularly scream feminine looking. My winter coats and jackets are admittedly outside the norm, but not outlandish. The one thing you could say about my wardrobe that is definitely unusual is my shorts, all of which are considerably above mid-thigh. However, it's not necessarily out of a desire to look feminine. It's out of a desire to create the illusion that my legs are longer than 18 inches. I believe I get by with it by dumb luck--that is, I have the right build and the right proportion to get by with it. I cannot recall in the 12 years since I've been wearing shorts from the other side of the store anybody saying anything negative about the length of my shorts. But yeah, I'm not really going for an overall feminine look.

When I think of feminising the male wardrobe I think more of borrowing from the women’s aisle than achieving a feminine look myself - in much the same way women will happily borrow whatever they please from the men’s aisle and then work with it to achieve the (still feminine)look they are after rather than trying to dress like a man. i like adding what are perceived to be feminine boots to my style, but I’ve no interest in looking feminine overall.

Today I stopped by a DSW store to see if my order was in. It was, but the Journey booties didn't fit. The bad news is that this DSW only has about 20% of floor space for heels, 10% men's dress and the rest sneakers (runners for you Brits). Very, very sad. So far this year I've only not worn knee highs boots to work once. I get lots of compliments on the my boots from both men and women. Random scooter shoot outs - "love those boots" or "great outfit". LOL Today when I picked up my food at a multi-restaurant eatery, the order taker told me nice boots.

I discovered a couple of days ago that even I have my limits, especially when I slack off on the conditioning exercises. I spent most of the day Sunday in 4 1/2" heels, which was not altogether unpleasant, but come Monday the bottom of my left foot was wanting to cramp up something fierce. It wasn't completely debilitating, but it also proves that I am not Superman. This picture is not new, but it contains the shoes I wore for the better part of the day, Steve Madden Daisie model.

I have had these wedge heeled rain boots for a very long time. They are supposed to be shiny, but they were in a corner covered with dust, and I wasn't going to take the time to clean them up just for this comment. I have worn them occasionally in the past, and they don't do a horrible job of pretending to be actually utilitarian. About 2 1/4" heels. Those Hunters with the 3 1/2" block heel look pretty sharp (for a rain boot), so of course they quit making them!