I pretty much buy Fitflop for all seasons now I've discovered they do winter footwear as well. Have just ordered and received some ankle boots, because although I have quite a few with a small heel I no longer find those comfortable to walk longer distances with. These new ones are perfect and look better imo than say a trainer. Fitflop are always mailing me, like most brands they have constant sales, so I take full advantage when they do, I don't think I've ever paid full price for anything.
For summerwear they probably have more lines, including, plenty of strappy type sandal that would go with a dress if that's what you are after.
Turning to handbags, they can be a hinderance when walking, I recently purchased a small purse/clutch bag from Radley, large enough to contain phone, a small wallet with cards, as well as some loose change, lipstick, keys. Very handy large loop, so can hang on the wrist.