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Like you, I would much rather shop online than in a brick-and-morter store. Unfortunately, that limits you to brands that you already know because you are confident in their sizing, fit, and quality. After a while, though, you can really get stuck in a rut.
A few years ago I took the plunge and made an appointment with the personal shopper at a nearby Macy's. At our first meeting she asked what my favorite brands were for work, casual, special occasion, etc. She asked about my lifestyle, which gave me a chance to really emphasize that my clothes have to be pretty hardy -- no delicate hand washables will stand a chance in my house! She took some measurements (the worst part by far) and started pulling outfits for me all over the store. I just stayed in the personal shopper's private dressing room and tried things on for an hour. It was like shopping with your mother when you were a kid, if your mother had a current fashion sense and knows every inch of a big department store. Half of what she brought me to try on was from the sale rack. She even arranged to have my pants hemmed by the in-store tailor. It was the easiest and most productive shopping trip of my life.
A year later when OPA's convention was in our city, I invited that personal shopper to lead a "What Not To Wear" workshop. I recruited local alumnae with four different body types (hourglass, apple, pear, and straight) to meet with her ahead of time and have her pick a trendy outfit that didn't flatter them, as well as one that did. Then during the convention workshops, they modeled both outfits while she described what worked for that body type and what didn't. The message was: don't buy things just because they are the current trend, especially if they don't flatter you. The best part was that the "don't wear this" outfit for the pear body shape was the exact same outfit the straight body shape was advised to wear. The fluffy skirt added visual inches to the hips, which just emphasized the pear shape but which added pleasing curves to the straight body shape. It was a HUGE hit with the delegates! And she was a sweetheart to help us with it: picking out the outfits and accessories, transporting them over to the convention hotel, then providing the commentary while the volunteer models strutted around.
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