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Try using gel eyeliner for smoother lines. It comes in a little pot and you apply it with a small brush. I bought this eyeliner a couple years ago, mostly for the wing stencil (which took some practice, but was actually a good tool), but it’s actually a good eyeliner and comes with a brush.

I also noticed that a lot of your makeup is drugstore. I’m all for saving a buck and finding good dupes, but I’ve personally never had much luck with drugstore eyeshadows. I’ve managed to score some really good deals on UD Naked palettes online, and it made a big difference in my eye game. They just tend to blend better and have more staying power. I also subscribe to Ipsy, and most months I’ll get an eyeshadow from a decent brand - sometimes they are amazing, and sometimes they suck, but at the end of the day I only spent $12 on the whole bag, ya know?

Finally, just wanted to say I can’t contour to save my life, and I think your cheeks look GREAT, and you either have super foundation skills or really good skin (or both), because I think your face in general is very well done.

Hi!

For this kind of look I'd personally recommend a cream or liquid eyeshadow, just because the color would be more intense and rich than a traditional powder eyeshadow and it will be easy to achieve this intentionally messy, painted-on look.

Here are some options:

• Revlon PhotoReady Eye Art in Midnight Glitz ($6.38), this honestly surpasses the quality of my higher end makeup, a beautiful metallic navy. There is a glitter on the other side which might or might not be your thing, you can just ignore it and use the eyeshadow side if not.
  
• Wet N' Wild Color Icon Stick in Blue Lah Lah ($2.99), this is more of a true cobalt blue like in your picture, without any metallic or shimmery texture.. The stick format will make it easy to blend with your fingertips.
  
• Wet N' Wild Megajelly Eyeshadow Pot in Something Blue ($4.99) another cobalt blue option, this one is shimmery though. This comes in a little jar that is easy to apply with fingertips.
  
  Good luck!

Skysong23 pretty much said it all but I figure that I would throw some more out there for you.
First of all she sounds beautiful! If she has blue eyes make sure to use blue and browns for eyeshadow, it will make everything pop! If they're green then use purples and maybe blues depending on if they're more green or hazel.
Another eyeliner technique is the tape method which I grew out of pretty quickly. What I do is when I go to wing it I take the edge of my bottom eyelid and continue tracing it up until where it would interject if I did the same with the top eyelid[Diagram] (https://40.media.tumblr.com/24b9121278b2140dcccbb676d354ed3c/tumblr_o2u8slx1JN1siggdso1_500.png). Elf is great for beginners (and cruelty free) I also suggest NYX which can be found at drugstores and some grocery stores. I also suggest the Jesse's Girl Eyeshadow Palette which I know is at Riteaid (it was way cheaper there too) but I don't know where else.

Lilly Lashes in Goddess!!! Literally no one can tell I have false lashes on and I get tons of compliments on how long and nice my lashes are, when I tell them they are false lashes typically they go in for a closer look because they can’t tell. Love them, also you can keep re-using them (I can get about 10 uses out of them or a bit more depending on how well I take care of them) just keep them from getting too much lash adhesive build up. I don’t use Lilly Lash glue though I don’t care for hers, I use Lavaa lash glue... much more preferred.

Link:
Lilly Lashes Goddess

Link:
Lavaa Lash Adhesive

Eyeshadow base: LA Girl Pro Concealer in Natural

Eyeshadows used: Essence My Only Eye Shadow Palette

Foundation: essence FRESH AND FIT Awake Makeup

Lashes: Eylure x Cheryl no. 114

Lips: Nyx Lip Lingerie shade Baby Doll

I use Almay Smart Shade Primer here. The green tint helps tone down the redness quite a bit. I'll combine that with a liquid foundation for serious coverage or a powder foundation for a more natural look.

I also find that my skincare routine is more important than makeup, especially in the winter. I like Aveeno's Clear Complexion cleanser and daily moisturizer because they contain salicylic acid which is supposed to help with redness and other skin blemishes. Salicylic acid in high concentrations help prevent acne, but can also cause redness and irritation; in lower concentrations it helps prevent redness, so check the concentration on whatever you choose. I'll do that every night and wash with water only in the morning. I think a lot of my redness comes from dehydration and this seems to have the biggest effect.

Flawless Brows

What about eyelid tape?