I love red lipsticks! They are my signature. My go to is Sephora Always Red, which is a lip stain. For a deep, dark red I tried the Kat von D Nosferatu, which is matte but has a wonderful luster to it. However I have found it can wear off unevenly, leaving blotches if you are not very sure-handed applying it.
For a wine-red I use a Tarteist Bling with an Urban Decay Hex lip liner, which gives a similar look to the Nosferatu. I usually wear a matte shade, but recently I tried Smashbox's line of glossy lip paints, and I do like Bad Apple, which is a red and shiny as it gets, but it is not a stain, and you have to be careful when you eat or drink, or even blow your nose. These are all mid-range products you can get for $20-25 each.
I recently tried going upscale and bought a Chanel lip crayon ($37!), No. 6 Framboise, which is a beautiful, creamy fuchsia, but it does does seem to fade fairly quickly and you have to keep reapplying it. Ironically, the product that seems to last the longest and works for me the best is good 'ol drugstore L'Oreal lip stain No. 223, Mesmerizing Merlot ($15). It has a top coat applicator and lasts all day (I am wearing it in my avatar picture).
~Terri