Well - to answer your & Augie's questions...
1. Wintertime: Most of my winter dresses are mid calf to lower calf length (for warmth). For upper layering, cardigans are great with dresses. In the winter, I wear boots for warmth and practicality. I have some nice leather side zip boots that are tall - just under the knee. For really bad weather, I have black snow type boots (Lands' End) that don't look tacky with my dresses. Taller boots are great because they keep you warmer and drier. They also hide the part of your legs that your dress doesn't cover so no need for nylons/tights! Also - if you wear long underwear under your dress, no one will know!
2. As for hosiery, I avoid pantyhose/tights at all costs. I loathe them. If I absolutely must wear hosiery, I try to get away with knee highs or thigh highs. But, if you wear taller boots, no need to worry about these.
3. Silk long underwear are sooooooooooooo comfortable. Lands' End sells them in petite sizes as well. They are a bit expensive ($25 per piece) but last forever if you take proper care of them and are more like an investment. Get white or ivory ones for lighter colored dresses and black for your darker dresses.
4. Summertime - I just wear my dresses with no hosiery usually. If it would be inappropriate for me not to wear hosiery, I try to get away with thigh highs or knee highs, depending on the length of the dress.
Good sources for dresses are Chadwicks of Boston www.chadwicks.com, Lands' End www.landsend.com and Eddie Bauer www.eddiebauer.com also try their outlet www.eddiebaueroutlet.com All of these sites sell petites - Yay!  Eddie Bauer and Lands' End can be expensive - watch for sales at their sites. Chadwicks always has items on clearance and you can find amazing deals, especially off season.
I have had luck with these sites because I am petite and if I wore "normal" sized dresses I would look dumpy! There are other places that sell petites too - Coldwater Creek, Barrie Pace, Nordstrom.com, L.L. Bean, .....I am sure there are tons out there. Probably one to suit anyone's taste or personal sense of style.
Good luck!
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Re: sources for dresses and long underwear...
