I have two suggestions, operating under the assumption that you're using a mid-range makeup counter budget rather than a drugstore budget.
Suggestion One: Go to Sephora, find a sales associate whose makeup you like (for YOU) and ask her to give you some product recommendations. I'm pretty sure they're also doing 45 minute makeover sessions for a $50 minimum purchase right now.
Suggestion Two: Go to a department store in your area with a good variety of makeup counters and hit up Bobbi Brown, Laura Mercier, or Clinique. Again, look for a sales associate whose makeup is similar to the type of look you want, and tell them that you want to change up your routine and style. There will probably also be a minimum purchase for a full makeover.
I like the Sephora suggestion, but don't be scared by the makeup artists who might be wearing looks that are a bit... erm... extreme. Sometimes, that's the look they're asked to wear by corporate, or is just their personal style. But that doesn't mean that they can't create a more day-friendly look for you, so keep that in mind. Also, going to Sephora has another benefit in that you have a huge selection of brands, something you won't find at the typical department store. They'll give you free samples to try at home, too.