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Looking at the photos, I identified some common pieces: great fitting shirts/tops that are classic, ditto for blazers. Strong statement accessories like belts, jewelry (necklaces and bracelets). You have good taste and a strong sense of style. That's half the battle. Study the photos and pick out what you really love. That's the starting point. Make a list.
Like you, I hate shopping. I struggled for a long time with the frustration of knowing what I like and not finding it in stores, and still do at times (easily overwhelmed with all the choices). Start out with ONE great piece. Find that blazer, for example. Then find a great shirt, and you're on your way. Build from there. That's what worked for me.
Oh, and shop when you don't need something for an event or occasion. That way you avoid the pressure of "I have to find something" and get stuck with something you really don't love.
Personal shoppers are terrific and I definitely agree with using one until you get really comfortable with the whole shopping ordeal. I can now walk into a store, spend about five minutes, and know immediately if I'm going to be buying or moving on.
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"One of the painful things about our time is that those who feel certainty are stupid, and those with any imagination and understanding are filled with doubt and indecision." Bertrand Russell, The Triumph of Stupidity
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