My least smudgy eye pencil, although not perfect, is Urban Decay 24/7. Do you know the trick of taking a small flat brush and running it over the pencil a few times and then using the brush to line your lower lids? You get a softer look that way and it is less likely to smudge because there isn't as much product. I find that is longer lasting than using a shadow to line, although going over it with a shadow can make it even more stable.

For droopy eyes, subtle matte shading in the crease and a bit above can help camo that. The right colors recede and help the droop look less.

For lips, you don't care for dark or bright...have you tried mid-toned nude-pink? Your Milk stick sounds like what you want, but if you'd like other suggestions I can look through mine and give you some names.

And yes, quite obviously I love makeup!

I really need to go and have a professional makeup update, since I've been all trial and error lately.

Some definite hits for me:

Nars Radiance primer (has sunscreen so i also apply it to neck and exposed chest) under their tinted moisturizer. Sometimes also their eyelid primer.

Charlotte Tilbury Exaggereyes palette: this is amazing stuff and lives up to the big bright eyes promise.

Urban Decay glide-on eyeliner

Charlotte Tilbury Red Carpet and Walk of Shame lipsticks.

I've really simplified in the last couple years to dark brown/bronze on eyes, bronzer, and wine or red lippie. I used to do plums or olive shadows sometimes, but decided I preferred the metallic browns. Occasionally I'll order samples to try different things, but don't buy once the sample runs out. The main thing I have to be careful of is to get dark enough colors!

Great ideas!
I am not a regular “ updater” but like to try new lipsticks, blush, or B&B. I don’t like the idea of spending loads of $$ though and am leery of “ branding” and yet I do fall for hype and buy things that then are not necessarily better than my drugstore items. I read reviews but there’s always +& - .
I like trying samples so want to do more of that rather than buying something packaged first.

I have been trying foundation/contour sticks. I like them. My skin is so much drier (sp?) now and I’m with Angie - dewy is the way to go. As I get older, also, I want to say I have started to worry about things that require ‘pulling’ to apply. Esp the eyes. One day I’m gonna need surgery for drooping eyelids so I can see(!)

Also, back to drying makeup - lipsticks can be drying too. I’ve got a lipstick that I need to find a replacement for. It’s frosted. Drying and also... stinks to high heaven with perfume. Bleah.

Janet, my eyes are super-fussy and sensitive, and I've had good luck with Covergirl Ink It eyeliner; they don't smudge on me and are easy to apply and never bother my eyes. That said, I had trouble finding the last time I looked so not sure if they've discontinued But worth a look next time you're in the drugstore; super cheap and cheerful.

trish macavoy gel eyeliner. i only use sparingly (in dots) along upper eyelid when going out special. otherwise, no eyeliner or shadow due to blepharitis.

i love estee lauder brightening primer and smashbox radiance primer. i use laura mercier tinted moisturizer.

estee lauder double wear undereye nconcealer.

i use cetaphil undereye cream with hydracoulinic (sp?) asap after showering. then i use clinique alla bout eyes. then the estee lauder concealer.

no primer under eyes or on eyelids. chanel mascara or loreal telescopic which i absolutely love for a low end mascara

I'm not a huge makeup experimenter, I tend to find something I like and stick with it. For the eyeliner, have you tried a powder eyeliner? I use one from Young Living (the essential oil company) that I brush on and it lasts all day and doesn't move around. I was quite surprised because I thought it would have the opposite effect.

I have a problem with lipstick colors, they tend to turn orange on me or very bright, so I stick with neutral or almost brown tones. Kkards black lipstick is intriguing.

I update every few years. I LOVE wearing the bit of make-up that I do. DAILY, no matter what. But I am not a make-up person at all.

I use light coverage foundation (Clinique), but have nixed any use of powder since my fine lines around my eyes are beginning to show and the powder shoes. My lips are pale so I tend to do a berry and red tones during the cooler season. Can't seem to figure out my eyes out but a little eyeliner, some light highlights and waterproof mascara. I rarely use blush.

I go on a make up binge once in a while. I wear primer foundation, lipstick, bronzer and eyeshadow daily. Like Janet I have the same smudge problem, I put a setting powder on under my eyes which helps a little. My eyes are very watery and there are certain eye liners I cannot do, one is Clinique it makes me positively cry. I'll be trying out some of the recommendations from everyone !

Janet, I have a Kat Von D Tattoo liner (in Trooper) and it is so fine point, you can make tiny, tiny dots under your lower lashes (highly recommend lighted magnifying mirror) and you create the illusion of a smudged line, but it stays put. I actually layer the Kat Von D with a Smash Box waterproof liner for a smokey eye look, and if the Smash Box wears off, the Kat Von D is still there as a backup.

I'm a makeup junkie . I admit it. Now I may not buy a lot of higher priced makeup, but I do get some by watching for sales and on birthday and Christmas(in the past I bought more when I was being irresponsible with my credit cards). I also watch a lot of YouTube,so the beauty recommendations I've seen work for others or that I've tried for myself I'll share.
Eyeliner: I've tried UD 24/7 in Perversion ( black ) and it works nicely , it came with the zip up Smoked palette.
I've also liked and repurchased a few times the Elizabeth Arden Espresso and Bronze sharpenable pencils usually in large holiday sets other colors from the line are nice too.
From Clinique, I've tried the micro fine pencils ,I got one in a gift set with a shadow palette and lipstick etc and liked it so much that I bought a set of mini pencils in several color options. These stay on exceptionally well- it's hard to completely remove all of it . Just don't scroll too much product up at once , because if it's up too high then it can snap off just like you wouldn't fully roll up a lipstick and then swatch or apply it - it'd be too likely to break.
In the drugstore side of things you may want to try Ulta or NYX eyeliner pencils in either the retractable or sharpenable kinds . I got several of these ( dove gray, some greens, blues and a bright pink ) I've tried both and they seem to be very good quality similar to the creaminess of UD or Marc Jacobs ( Sephora bday gift one year also quite good- I didn't try the KVD birthday gift which included the Tattoo liner as I won't support her brand [racism,pedophilia normalization,and other issues] though I've heard the product quality is excellent) .
Loreal Silkisimee sharpenable pencils are very good . I've got the champagne and cobalt blue colors.
Milani , Maybelline and Cover Girl all have good sharpenable pencils.
LAColors at Dollar Tree or Dollar General is good in the brown black retractable pencil I've bought at least five ,but avoid the navy - it melted down my face finding heretofore unknown eye wrinkles !
I'm trying more colors as I find them , the price is only $1!
I also like Mary Kay for eye and brow liners and eyeshadow ( though I almost like the discontinued oval ended eyeshadow more than the current mineral line - mom used to be a consultant)

For lip recommendations I second the motion for trying Clinique Black Honey almost lipstick . I like it and have gotten my mom and my boss hooked on it too . Emilynoel on YouTube loved it and got me on it . Her current fave is the Chapstick blackberry tinted lip balm it looks to be very similar and at a lower price point. If you go for the Clinique, I also recommend the lip chubbies and the blush pops ( I have ginger and Heather pop and fully intend to eventually get cola and coral and maybe nude pop) I've used the blushes as eyeshadow on the crease and lid on busy days for easy monochromatic looks. Bronzer and highlighters can double up too.
If longevity is an issue, eye primer can help. I've used elf and wetnwild and liked the results. In higher end Lorac and UD .
I've tried Rimmel eye primer and haven't been impressed won't repurchase,but to each her own.
I've heard very good things about NYX, Milani,and Too Faced as well as Ulta brand eye primer.

I love makeup and like Angie, I wear it daily. I can second a number of the recommendations here.

I always wear eye shadow primer because it really makes my eye shadow stick. When primers first came out, I was a doubter. They never really worked for me. But they've changed a lot in the last decade or so. They really make a difference now. I use either Urban Decay or Two Faced. Both are great. Make Up For Ever (MUFE) is also good, but I find the other two are better. The Urban Decay options include one for mature eyes that is meant to blur lines.

I adore Kat Von D liquid liners. They really stick. I cannot live without my Marc Jacob pencil liners either. You put them on, smudge them out, and then they set in a way that is almost unmovable. I think they are better than the Stila and MUFE ones, which are also quite good. If you tight line (and really, everyone should), I cannot say enough good stuff about the Marc Jacob mini liners and the ones from Hourglass. Marc Jacobs, Stila, and Hourglass lines are mechanical pencils, which I vastly prefer. MUFE are wood ones you sharpen. YMMV, but I own the Laura Mercier cake liner that Angie loves (it is probably my third of the same), and I don't find it holds as well as the pencils. I have oilier lids, so things migrate unless they are really tough. The Laura Mercier smudges all over on me. I have to use a special setting liquid with it for it to work for me.

Foundation is too personal to specify. People are really picky about what finish they love, how a color looks on your skin, and how your skin reacts to the formula. For me personally, I've been using Kat Von D concealer for spot coverage most days and Kosas tinted face oil when I want fuller coverage.

Finally, I never thought I would recommend it, but Charlotte Tilbury's Filmstar Bronze and Glow is amazing. Really amazing. I tend to stay away from those things because "glow" usually means "highlights every single fine line and wrinkle your skin has ever though of developing," but hers is magic. It somehow highlights while softening lines. It gives your skin that plump, reflective look that well moisturized, bouncy skin has. If I were to recommend one thing to someone wanting to brighten their look, I'd recommend that. If I were to recommend a second thing, it would be one of the fine liner/tight lining liners from Marc Jacobs or Hourglass.

I didn’t realize it before but I have makeup capsules! They are divided by color and season. I agree with everyone here who mentioned primer. I use the primer that goes with my mineral line. I have to say that mineral makeup does not smudge or wash off when I swim or get wet. I need to remove it. It sticks.....

A shout out to Bobbi Brown gel eyeliner in a wee pot. It is less harsh than liquid liner and they make a nice bronze/brown that really suits me. It lasts far longer than pencils. I really like the Urban Decay eye pencils, but they don't last more than half the day on me.

My unicorn is a lipstick that doesn't irritate my lips. I love lipliner and lipstick and look so much more alive with them, but everything makes my lips or the skin around them itch and burn. The fallout from steroid eczema creams in my youth.

Bobbi Brown lets you "try on" lipstick with your phone, so at least I can imagine myself in a bright red!

So many great responses and ideas! I’m on my phone as usual and can’t respond to every one, but I am reading all with interest and taking notes.

I use UD eye pencils and I love the colors (Rockstar is a favorite) and how smoothly they go on, but they do fade during the day if I use them on my lower lid. Even with foundation primer but maybe I need to try a dedicated eye primer if there is one that’s gentle enough.

I do really like the Milk cream blush I got! The color and consistency are very nice and natural.

Still a fan of Laura Mercier tinted moisturizer and good old cheap Maybelline mascara in the pink tube.