I think you'll fit right in. This site isn't primarily geared towards what we might consider "crossdressers" or transgender people though both groups have active members in good standing here.
As for my own personal situation, I had a phase early on when I questioned my gender identity. I wondered if I would lean towards transitioning to full blown woman-hood, and there for a while considered myself "gender neutral".
But after the novelty wore off of wearing skirts and other feminine clothing, I finally settled on simply being a "guy who likes pretty, feminine clothes from time to time". It need not define me.
I came to peace with what and who I am on the inside and ceased to be railroaded into whatever classification society wanted to place me in, and with this peace, I found a freedom like I've never known before.
I am what I am.
Now there is a statement nobody can debate.
I've been thinking a lot about the differences between
- wearing a skirt,
- wanting to feel feminine,
- androgenous/gender-non-conforming style,
and coming to the view that these are all different things.
Even accepting that gender roles are social constructs, wanting to wear a skirt in order to express femininity is not the same thing as wanting to wear a skirt and still express masculinity. Both are ok, but it's important to recognise and accept that basic distinction.
a. You can wear a skirt without being feminine (kilt).
b. You can dress feminine without wearing a skirt ('womens' trouser suits)
c. There is non-conforming/androgenous style (which tends to lean more towards the acceptably male than it does the other way). I often wear tights under mid-thigh length shorts; not exactly feminine, but not exactly masculine either. My sister described it as 'a bit gay'.
Of course it's wrong to judge people by their clothes, but it's an unavoidable fact that we all do. Fashion is a public act. It doesn't help that some styles have evolved specifically in order to make a statement (a quick search for 'gay style' will confirm this).
Yes, you should be able to wear whatever you like without fear. But that doesn't mean you're automatically gonna look awesome. If we're going to break the rules - precisely because we want to break the rules - we need to understand how to reconcile how we feel with how we are perceived by others. I spend a lot of time on Pinterest, looking at ensembles that I think look awesome (and a lot that look terrible). Then you have to consider, how does that work for me? Do you need to oversize, undersize, slightly longer, slightly shorter? Where do the lines cut your limbs? Do they enhance or detract from the naked you? The male body shape is different to the female - we tend to have proportionately longer torsos and shorter legs. It's easy to look like a block with two sticks poking out below.
At the moment I'm exploring non-conforming style quite a bit. My ambition is to expand the definition of what counts as a masculine skirt beyond the constraining limitations of the kilt. I don't have a strong ambition to look 'feminine' (but I'm ok if you do). The other day my new 'tactical/utility kilt' in plain black ripstop fabric arrived in the post. I'm quite excited about this because it's a garment that can be worn casually - a traditional kilt is very formal and dressy. The new kilt is also the perfect length I think (for me) - an inch or so shorter than the regulation 'on the knee'. (Current fashion, especially among younger men, is favouring a slightly longer kilt look, below the knee. I suspect this is fuelled by social uncomfortableness about the exposed male leg, with long shorts 'in fashion' and short shorts 'not acceptable'. I recently read a review of a pair of cycling shorts which described them as having 'a touch of the magistrates court about them', which seems to me to indicate the basic social fear that underlies contemporary male fashions. I grew up in the 1970s, when it was ok for men to sport all sorts of traditionally female looks: permed hair, pink shirts, ruffles, short shorts. I owned a pair of embroidered lilac jeans. Happy days!) I teamed up my new kilt with black yoga tights, an oversize black hoodie, thick black socks, and tan coloured hiking boots, and immediately went off up the town for coffee and to show off.
Beyond being a person of color who’s also a skirt wearer, something of a rarity in itself, also, I don’t see myself as being a crossdresser or tranvestite, even though I wear women’s clothes from head to toe when out and about, including heels, earrings and a purse, I prefer to be called a “fashion freestyler”. I don’t at all feel feminine when dressed, but I certainly enjoy wearing the clothes and accessories, the experience makes me feel good because I’m garbed in the clothes I love. But, that’s just who I am, I don’t expect you or anyone to follow in my footsteps, the important thing is to follow you own path and be happy in the course you take.