I love my Beauty Blender but hate cleaning the thing and find it all too grim to use again once used. The Real Techniques version is supposedly almost as good as the BB. I do love the flawless finish it gives even with sheer bases so on balance the cleaning faff is worth it and much preferred to brushes and hands. I do concealer and other cream products with it as well so find it very versatile.
So basically you want to look groomed but not with the look at me I'm wearing a week's worth of makeup type makeup? Natural but noticeable enough?
I'd say get the brows sorted (consider getting them tinted if fair), Anastasia Beverly Hills Brow Wizz (though Nyx do a cheap dupe if you can find it), or the Dip Pomade. Laura Mercier recently released a brow gel with fibres to bulk them out a bit which I quite like.
A good base, depending on coverage. I like Laura Mercier TM best of all for sheer to medium and Giorgio Armani Luminous Silk for a bit more coverage.
Laura Mercier Translucent Powder as a setting powder.
Charlotte Tilbury, Bourjois, or Chanel for blush. CT and Chanel also great for lips.
Everyone and their mother will harp on about Urban Decay and their Naked Palettes for eyeshadow, they've just released a new one which I think is actually a really nice one as a starter palette for day (it's all matte).
Concealer sort of depends on how much you have to conceal. LM Secret Camouflage is good for little spots and blemishes. I like the Charlotte Tilbury Retoucher (but you have to use it quite quick as the colour tends to go off in the last month) and Giorgio Armani Precision Retouch Concealer for underneath the eyes but I don't have much darkness there.
Look at Lisa Eldridge on YouTube for some inspiration, she does the made up but not overdone look very well.