Now, men may think that women over-analyze clothing and shop waaaaay too much/often, but really, gentlemen, you just have to get variations of the suit. The only patterns are pinstripe and solid.
Give us females a little credit.
We have suits, dresses, tops, bottoms. Dresses: wrap, sheath, jumper, with sleeves or without, empire, natural, and drop-waisted; Skirts: pencil, a-line, flairy, high waisted, low waisted, side zip, front zip, back zip; Tops: cropped, long, hip length, 3/4 length sleeve, wrist length sleeve, elbow length sleeve, button-down, pullover, cotton, wool, polyester, thin enough to require underlayer? Then a search for the underlayer and so forth. I haven't even mentioned shoes yet.
Men, I request that you do not mock the process.
In order to look one's best, analysis of the body type should be done, which is categorized as to where weight is usually stored. There are two basic fruits mentioned:
1) Apple: after 5 pounds of matzah, my stomach protrudes.
2) Pear: the 5 pounds go to the hips and the . . . ahem . . . derriere.
As an apple, the best skirt style for me is the pencil. In times of post-Pesach weight crises, I wear a peplum jacket (awesome style for apples - the jacket flares out after the waist, hiding the boch) to camouflage the front territory.
For the pears, "poofier" skirts are the better option—but they should not be worn with long tops. I have seen this style on pears, and can testify as to the perfection of suitability.
As for skirt length, the general consensus (even amongst the glossies such as Vogue) is for the hem to end right below the knee. Calf-length emphasizes the most unflattering area, and ankle length is fine for the weekday but I don't think is sharp enough for Shabbos or simchas.