I despise dresses

[Gertrude]

I wear a skirt regularly as a man. At least once a week while running errands.

You're a man?

[Gertrude]

Do you have a specific reason for this?

I have kilts for man mode.

[GordonG]

You're a man?

Yup. Although a feminine one.

[Margarine]

I wear dresses 90% of the time when out and about, wear jeans and a top when doing yard work. I have found lands end has a decent selection of plus and tall sizes. Now that I range from size 14 to 16 the selection has gotten much easier. Just stuck with a lot of 20W to 24W dresses.

[Maid Marion]

Shop different brands until you find one you like.   Sizing can be pretty consistent within a brand.

Another approach is to figure out your body type and then choose styles that are most flattering.  And avoid the ones that aren't. 

This even applies to colors.  Figure out the colors you should wear based on your skin tone.  And undertone.