Yep! Take a friend.
I've shopped 2 times so far... My daughter is trying to get me into "cute" clothes, and I feel they are too young (she's 15 and giggles when we are sharing clothing). The second time I was with a high school buddy of mine, so we're the same age (almost 40) she was very good at helping pick out "appropriate" clothing. Not old and frumpy (because that's how I've dressed for a decade) and not teenage.
Oh, be sure to take a friend who knows how to look good!

Another friend wasn't so helpful...she dresses how I've dressed for so long.