Whenever I need a fashion pick-me-up, I walk into Bob Ellis Shoes and look around for Catherine. Catherine Waring has been providing her customers expert service for more than 12 years. She, like all of the Bob Ellis staff, goes the extra mile—keeping notes on her customers’ needs and e-mailing photos of products as they arrive.

Recently, I dropped in to say hello. I wasn’t planning on buying anything (though it’s tempting to browse, since Bob Ellis Shoes carries many high-end designers and exclusive styles). But I did have an uneasy feeling about my handbag, which was merely “functional.” Just how important, I asked Catherine, is it to carry a nice-looking purse? “A great handbag and a great pair of shoes,” she said, “make the outfit. It doesn’t matter what else you’re wearing. You’re just instantly there.”

Catherine is not a hard sell. Rather, she uncovers what you always knew about yourself, specifically, an innate appreciation for the finer things in life.

The bag I was eyeing was a whiskey-colored satchel by Chloé. She pointed out its advantages: a more structured body (it wasn’t a “feed bag”), a zippered top to keep things inside, pockets on the outside, wrapped-leather handles that drop out of the way, and an optional shoulder strap. Furthermore, the bag had passed her “bag of the day” (BOD) test. When a new bag arrives, Catherine walks it around the store, testing how it handles.

Other bags caught my eye. There was a stunning black python-and-stingray clutch by Khirma Eliazov and a small Givenchy satchel in the popular “baby bag” style. (Baby bags, smaller versions of larger designer purses, go easily from office to dinner sought after by petite women.)

I walked out leaning toward the Chloé. I just needed time to think. Catherine agreed. “Go next door and get a frozen yogurt,” she suggested. “You’ll be back in 15 minutes.”

One thing I’ve learned about Catherine. She’s always right.