skirtcafe.org

Greetings from middle America.!

Sounds like you are having an amazing time at it.
Regarding dresses, While I have had a dress or two. It is a bother to find one that really fits the male frame, especially my middle aged, flabby guy frame. They just don't fit quite right most of the time. So after trying on about 50 dresses and only finding 2. Over the course of 5 or 6 years I gave up on dresses.

I find skirts the best way to go. the waist measurement is the only really critical measurement. Just pair your skirt with one of the shirts in your closet. You can dress up or down the same skirt for alot of types of skirts.( It's hard to dress up a denim skirt, or athleasure skirt) check out Some of the ways men can casual or formal the same kilt. I avoid taking my skirting cues from observing women. After all, I'm going for the Men in skirts look. So you can dress differently and look good, be comfortable while doing it. Most of the time I just wear a t shirt or Polo shirt.
Like others already Said. Check out secondhand shops,
You can get the best deals there, and usually quite a variety. This can be both good and bad.
A lot of options is good, but It might mean leaving the store with a bunch of skirts. I have way too many now, atleast the average cost per skirt is around 5 dollars.
Enjoy the hunt for a great skirt. Best wishes in the great skirt adventure.

Hi Pete, and belated welcome.

I was also surprised how little comment my skirts got at work. As my work was retail, I was meeting members of the public all the time, and there too, very little attention seemed to be made, never more than confused looks, (only few of them) and the extremely rare frown. Lots of compliments. With the kind of skirts I tend to wear, the "Nice Kilt!" comment is much more common than "I love your skirt!" From your descriptions, it seems you have correctly made the decision to make an effort in coordinating your male accessories, and make a believable look. I joked to one women who complemented me on how well I'd put things together with "I didn't want it to look as if I'd put the skirt on by accident!"

Another vote for thrift stores, trying to find suitable skirts from years fashion is a limitation. Plus I often experiment with a style, and the $5 price tag makes that much easier with the many failures.

Dresses, I have mixed feelings about those. My view is most tend to exaggerate feminine characteristics, though then you get into what should be considered feminine. More factual are the physical issues, I often find armholes too small, and shoulder to waist ratio is often not suitable. I steer away from anything that emphasizes the bust, or has too low a neck line. Full length sleeves almost always end up too short as well. If you want one fitted to you, look up eshakti, crfriend has some dresses from there, I haven't yet, though my GF ordered several, and was delighted with the fit, and she is almost as hard to fit as I am, though for very different reasons. Plus they usually have pockets!

Like you, the vast variety, and the sense of freedom it brings led me buy far too many skirts, and now have to re-donate a bag or two.