I think Lucky has a great website, too, and one of my favorite features is it's "Does This Outfit Work?" segment. The gist is this that a real-life gal will submit one of her go-to outfits to Lucky and get the magazine's honest take on how she's put it together. Lucky's team will add a few new pieces to the look in an effort to elevate it, then accepts comments from readers on the site. Sometimes the new outfit flies, and sometimes it doesn't, but I always get the sense that the staff doesn't care. They're too cool to turn their noses up at constructive criticism.
You can check out a video of how the outfit is restyled here. Lucky ended up chucking the brown tee for a more fitted, yellow tank, and replaced the flats (not pictured here) with some strappy, wedge heels.
I agree with Lucky's opinion that the shape of the top should be more fitted in order to create a streamlined look, but while they didn't like the color of the original tee at all, I still think the brown really works! I liked the flats, too. Flats on a tall, slender lady like this one easily look simple-chic rather than frumpy.