I also think what you have on in the pic looks nice, but you know best how things look to your eye IRL.

I find the bold lip a challenge as well (as a lower-contrast person with warm-toned skin and the full lip thing @carambola mentions). But the main issue for me has been that most red lipsticks are blue-based...the landscape is very skewed toward cooler-toned people, and that can make it way harder for some of us to hunt down something that works. This may or may not be your issue, of course, but in case it is...

The one bold red I've found that doesn't make me cringe is Revlon's Ravish Me Red, which is a matte and can be drying, so be forewarned about that (deploy balm as needed? I dunno). I like the vintagy matte look myself, can be a matter of taste.

One sheer red I have found pretty easy to wear and that I think would work on neutral-to-cools possibly also is Revlon Colorburst Lip Butter in Candy Apple. It's not as bluey-candy-apple as one might think. So maybe not all that bold, but a bit more of a finished look when you want it.

I actually prefer orange lipsticks and have been collecting some...but they are not everyone's cuppa.

I am not sure it looks good on me but I do not feel comfortable wearing a bold lip of any color. Remember brown lips? Or white?

Claire, I think you have an excellent point about lipstick fashion. I don't think red is in fashion. It's fashion art right now, but not fashionable, if you know what I mean. Which is maybe why I used to like to do it but not now.

I also think makeup used to be heavier and we were all used to seeing it heavier...

Looks like I have a lot of company!
This is Revlon Lacquer Balm in 150 Enticing. I tried it again today with a swipe of Clinique Sunset gloss over. Kind of a shimmery golden tone.
Interestingly, the browns of the 90's look really good on me. I loved a certain Cocoa gloss that got discontinued.
I'm not looking to make this my everyday look. To Dianthus's point, made up isn't really congruent with my overall look. I mean, I use hairspray like 5 times a year.

@rachylou, I agree, make-up was SO much heavier in the 80s. Just watch any old work-out video and you'll see! Even glamorous red-carpet looks have a natural feel to them these days. The skin anyway, looks glowing and natural even if the eyes are smoky or the lip is bold. We caked on a lot more thick foundation back in the day.

Mo, yes I can see you in a brownish tone. Like a terra-cotta or something.

I am thinking it's too orange for you, at least on my monitor. Maybe more of a blue-red?

I am a burgundy fan and could never do bright red. For the really bright colors, it seems to me you need to balance the dramatic lips with dramatic eyes, at least to my thinking. Then it all becomes too much work, unless it's for a special occasion.

Personally I think the smokey eye and nude shiny lip is so Kim Kardashian. And so not what I want.

I've always had a poisoned eye for a bold lip. There, I've finally said it!

Actually, I think it comes down to personal preference. My eyes and hair have always been my best features so I'll play them up over my lips any day. I'm also with Ms. Mary in finding a bold lip really aging once you get older. Maybe it's because I get flashbacks to Joan Crawford in Mommie Dearest and Bette Davis in What Ever Happened to Baby Jane.

I'm so over the nude lip. That says *dated* to me.

And agree on the aging properties of matte bold.

I think a stain is more modern than a stick in general.

Mo, are you thinking of a red lip for special occasions? It might help to see the lip in context with any other makeup you intend to wear and the outfit.

I'm beginning to think that there are two camps -- the natural/nude lip camp and the non-natural lip camp. I'm finding anything that veers too far from my natural lip to look aging on me. So the smoky eye/nude lip has been my default for awhile now (unless I go goth -- that's a totally different look).

I'm finding that as I age and my hair turns from black into charcoal and my natural lip color gets lighter and lighter, my old nude lippies make me look washed out. Also, everything but everything seems to turn a nasty orange on me. I still don't like truly BOLD (bright) lips on me, but I'm getting to like somewhat DARK lips on me IYKWIM. Darker lips don't shout "Look at me!" the way a true red or scarlet do, but I'm having a hard time finding the right shades (tones?) that aren't matte. I'll be ordering Lipstick Queen once again from Nordies, because their texture is really nice and returns are easy. So far, Vincent Longo's Vanguard is a favorite, but I would only get it on a Triple Points day.

For me there is a difference between a Kim K nude lip which says 'I'm wearing a thick paler beige than natural product and maybe outlining it', and wearing, I dunno, clear carmex lip balm or something where you just look like a person with slightly shiny lips.

I'm not so into nude creamy lipstick, but all about 'natural' nude as in, not wearing anything that adds a tint and maybe doing more with the eye.

Cathy, yes, I was thinking of just going out date night kind of scenarios. Or sometimes when I'm bartending, filling in on the night shift on Saturday nights it can feel more 'right' for the atmosphere. Here is a lipstain I used for that exact occasion in this photo.

I like red lipstick, but I always feel like I have to dress up a little extra to wear it. I do always wear makeup, too, but red is not my go-to color. I think you look good in it (both first set and last set of pictures) and that it works for that more evening kind of look.

My first thought when I saw the lipstick was that it was too orange/warm for you. but as I took in the rest of the outfit and your blue eyes it grew on me.

Red is hard. But you can carry it off! Here's what I use, and since we have some coloring in common maybe these will help?
1. MAC: "Russian Red." A perfect, nearly neutral red. Looks orange in the tube but really goes on pretty pure. Must use a pencil (I use Brick) with it but it's matte and like something out of the 40s. If I want to really tart it up I'll put a dot of gloss on the lower lip. I usually ONLY wear this now for the most formal/glam occasions or when I'm wearing a high contrast outfit: pure black, Navy and white, etc.
2. MAC: "Hang up" my new current daily wear red. See pic number one below. It's a plummy shade of red is which more wearable for most women. It would go well with your coloring. It's bluer, and it has some shine to it so it's not so opaque.
3. MAC: "Fetish" which is my nude. See pic #2 below. It's hard for me to wear warm browns as a Soft Summer so I was glad to find this one. It's a very cool brown with lots of shine and metallic in it. I wore nude today because I was wearing bright, and I do mean bright red corduroy pants and didn't want them to fight.
4. MAC: "Rebel" which is a near fuschia that I wear when I'm feeling particularly feisty. Also needs a pencil.

I think you look great with red lipstick--I like the second set of pics much better than the first. I think the first shade may be too orange-y. Also I think the soft waves with your hair down go well with the bright red--very glam.

Have you tried a more sheer lipstick like Clinique Black Honey? Or Dior Lip Addict, which is a lip balm that is supposed to turn your lips the perfect tint on you? I find that they are too subtle for me, because I'm used to wearing a bolder lip myself, but they might work for you. I really like wearing bright red lipstick myself, but maybe it's because I tend to look better in high contrast looks and black/white and red, rather than pastels. In fact I bought a tube of Chanel red lipstick and lip gloss for my birthday last year!

Mo, FWIW I think the color looks great on you!
I wore lipstick daily when I was working at an office, but now that I work from home I don't bother.
I also find it really annoying that everything that I put on turns purpleish or bluish on my lips! I never head a true red lip color, but more burgundy and brownish and these look deceet, but when I tried a few corals, it did not end up coral on me but kind of weirdly purple-ish.

Also, I don't think it's necessarily the red lip itself that is aging. It's a combination of matte red with a thin lip (since lips tend to thin as you age) and heavy powder and makeup that make me think "aging".
http://www.allure.com/beauty-t.....aging-stud
http://www.huffingtonpost.com/.....64807.html
I would go with a lip stain or gloss for a dewy red look like the one in your pics.

I don't do a bold lip either!
I notice that Deborah, who is low-contrast in colouring, does is beautifully, and yet for me it looks costum-y and obvious.

Okay, now that Clinique Honey has been mentioned 3 times, and I remember Kelly recommending it months back, I will have to try it.
I've never been to a makeup counter, so these are all drugstore attempts.

Well I'm firmly in the camp of bring on the bold red lippie! I adore the contrast of a bright red lip with my pale skin and salt-n-pepper hair. But having said that, you have to be comfortable with that "in your face" kind of color. I think of a red lip as classic and timeless - like the little black dress.

Plus as someone who is fairly pale, I find I have to "wear color to have color", if that makes sense. Put a nude lip on me and I look like I'm ill. Put a bright and strong color on me and BAM, I look awake and bright.

I actually quite like this color on you Mo. But it takes getting used to and isn't for everyone.

I don't think they sell Clinique in the drugstore but you can order it from Nordstrom. Also the Dior Lip Glow. Example pics below. Lip Glow doesn't do anything for my lips though...I don't see a difference. Maybe it works better on pale lips. The Black Honey does work but it's very sheer, I'm used to a bolder lip now. I would see if you can try before you buy (although I do think Nordstrom will always take returns).

I think you will look incredibly striking wearing a true red lipstick Mo, but I sense this will be on the days when fashion is used for roleplay. I don't find a red lip a natural playmate for your everyday athletic outdoorsy persona but I would love to proved wrong

I had a Beauty Control red lipstick that worked for me back in the 80s, and I think I rocked it, with a bold eye and masses of shoulder length curly perm, ha! But I was a *lot* younger (20s), and I had more lip geography then. The very same color would look harsh on me now. I do have a translucent lip color (Fresh Passion) that is essentially chap stick with tint that is very red, and it is fine if I only use a little, and keep it sheer. But if I get too much on, that self corrects as soon as I see a mirror and scare myself! I sometimes see women who are my age-ish and I Think Thoughts about how their choice of lip color is not doing them any favors, and it looks harsh instead of flattering. I really don't want to be that woman.

I think eyes and lips both can fight for attention if they are both trying to make a statement, and it can look too "done" or something else scary and not appropriate for most people's jobs. If I only get one, I pick eyes. I know lots of women who pick lips and who rock that look, and just wear a very neutral shadow. I look for an everyday lip color that is essentially a slightly darker version of my natural lip color. Fresh Sugar Rose is good for me.

It does take a bit of getting used to - I am there now with the red lip - but initially it felt too obvious. If you have the lipstick I would give it a go on a couple of different "low risk" occasions to see where you sit (ie to work once, out casually, not for a big party!). You can wear red well - I am not the person to ask if this is the perfect shade or not because I am not that great at picking those details.

Further to Kiki's comments, I agree about competing lips and eyes. I don't wear eyeshadow or liner at all and only a swipe of mascara since I have fairly small lashes.

I just remembered that UK makeup artist Lisa Eldridge has a lengthy video on her website with all sort of red lip tips. Check it out: http//www.lisaeldridge.com/video/25389/ultimate-guide-to-red-lips/#.U8WbBhztV8E

I don't like a bright red lip on myself either, although in theory I have the right kind of coloring for it. I think it's because it's too glam/bombshell for me, which is like my anti-style persona. Also, it requires a LOT of maintenance which I just can't be bothered with. (I.e. you have to refresh it after eating or drinking anything!)

I prefer plum/raisin shades personally, both lighter (which is like "nude but better" on my natural lip color) and darker, which is a llittle vampy/goth but I still like it. So I don't mind a high contrast or bold lip color, just not bright red. I actually really dislike lipstick that is lighter than my natural lip color on me.

I don't like it on me, either. :/

I think you look good in the red lipstick; the shade looks good to me, although it's hard to tell color on the computer. I have trouble with some red lipstick myself, though, and as others have said, I find it's a matter of getting used to the look, partly. Getting the shade right is another thing (not too yellow, not too blue). And then there's the intensity, which makes it difficult to maintain throughout the day, as Diana notes. I saw a site (linked from a YLF forum post, I think) that recommended wearing a darker lipstick for daytime by applying it with the pad of your ring finger. I tried that with one of my matte darker lipsticks, and lo and behold, I like it much better. It's a softer look and feel, but still has a nice rich color.