Super thread! Thanks for posing this question, I love posts that get me thinking like this. I never wore lipstick until I passed 50. I used to believe I started doing so because I needed something to brighten my grey hair and give me a more polished look. However, I've always had fade-together light skin and hair, and I've followed a polished style since I put the 80s behind me. So the question about lippy and confidence gets me thinking: I definitely grew into the 'don't give a d***' attitude everyone says comes with age. Perhaps the lippy wearing is more connected to that than I realised!

I also want to thank Staysfit for her comment. Until now it hadn't dawned on me that lipstick colours *can* change on the body. I struggle to find the right colour, and, whenever I think I have it, I stop liking it the moment I wear it. Like Beth Ann, I have a drawer of lipstick, but for different reasons. I seem to do best with lip stains and a coat of sheer or gloss, but they're not very portable for touch ups. I've had some luck with the Jane Iredale "forever pink" that's supposed to change to match one's complexion. But I'd like something bolder -- and when I tried their new red version, it turned clownish. If anyone has advice on counteracting how lipstick colours change on the skin, I'd love to hear it.

Ditto. This is a great thread. My addition is about the shade and the level of confidence it represents I think. Going bright red or pink is what I do when I do feel self confident in my overall look and 'happy'.

Not bringing attention to self in that 'fail bright women' way is cultural and familial and I think you're right in feeling its connected to concepts of modesty, attention seeking and an almost inverted snobbery associated with the 'need not to highlight' your achievements, maybe?

Interesting, Shevia. As far as lipstick is concerned, I've worn it since my teens and wouldn't feel dressed without it.
For me, styling myself is a juggling act between camouflaging the worst and accentuating the best. I think I have a realistic and mostly-positive body image, and a similar concept of any other aspects of myself. I respect humility, and wouldn't want to over-promote myself, and, yes, I would feel uncomfortable being dressed to the nines, or in anything overly bodycon.
I'm happy in my skin, especially now that I'm older, and dress in a way that makes me feel appropriate and confident.

What an insightful question! I think letting oneself dress well/look good in general requires positive self esteem. On the other hand, I find that if I'm not feeling good about myself on a particular day but can make myself put the effort into wearing a nice outfit/doing my hair/putting on makeup, I usually end up feeling better about myself as a result.

I wear makeup practically every day (every working day for sure), but only wear lipstick when posing for a photograph. I wear chap stick during the winter, and that's about it. Most of the time, I don't wear lipstick, even if I have a full face of makeup on. I apply my makeup rather sparingly, though, so I don't think it looks odd to skip the lipstick.

Interesting thread and questions! I just skimmed -- I'm going to read more carefully as I drink my coffee, but I thought I'd do a quick response to this: "Do you style yourself to highlight your best or camouflage your worst? Do you feel self conscious about dressing to the nines? Do you hold yourself back in other ways?"

I feel like I style myself to do a balance of highlighting and camouflaging. Like Elisabeth said, you just can't hide some things. I'm never going to have a small nose or slim hips, and no amount of camouflaging will hide those things, so I usually turn to playing up the things I do think are more assets: my eyes, the length of my legs or the relative narrowness of my waist.

I only feel self conscious about dressing to the nines if that puts me way outside of the environmental norm. If the occasion fits, I love being dressed and styled well!

As for holding myself back in other ways, well, I could probably write a book on this. I have had self-esteem issues my whole life -- so many of us women have. So much of it is tied to perfectionism, too. I have overcome a lot of my fears of looking foolish (otherwise I never would have taken up running!) or worrying what people think (giving up a career in a field in which I had a masters degree in order to pursue a career in which I'm self-taught as an artist). My husband calls me out on it when he witnesses me "holding myself back," which is good. I think my increased courage in life in general has coincided with my journey to find and evolve my personal style.

As for lipstick, well, I like it and I wear it nearly every day, but bold lips look awful on me. I use it just to give my lips a bit of definition and polish. I feel more confident with a bit of makeup -- nothing too bold.

This is such an interesting question. The short answer is "No, I don't need positive self image to wear lipstick"; the Why and How is a bit longer.

Up through college graduation I really did not pay much attention to fashion. What my peers were wearing was (1) ugly to me and (2) would not be flattering or would be inappropriate/difficult to fit on my height and build. I had no idea where to start otherwise and no money to pursue it.

But one of the things I did discover on the interwebs of those days was true vintage style, and that other people out there were wearing it, and the hair and makeup, for regular clothes. Just because they wanted to. I bought a few things on ebay and was hooked. Things fit me! And they looked good! I really started to have fun with what I was wearing and in outfit creation. The aesthetic was ordinary 1930s and early 1940s street wear and business wear; not costumey at all.

I learned how to do hair rolls, and experimented with various ways to curl my hair. I found some basic makeup information; with the exception of the overdrawn lip, 1940s makeup is fairly natural and I learned excellent basic information. And I tried red lipstick.

I'd never really worn lipstick before. Colored chapstick, and a couple of just-darker-than-nude light coverage things. Red was a huge step, and it took a while to get used to it. The first day I was very self-conscious, but dedication to the look kept me trying. I experimented with different reds, and it became my signature. Months later I tried my old nude lipstick and felt so colorless and blah in it. My self-image had changed and I liked myself with a stronger lip color.

I'm an introvert and shy, but in vintage wear I discovered something I
loved. I wasn't hiding; I was learning what I liked, and in the process I
found confidence.

I wear make up everyday and it is definitely to hide "my flaws". I have very pale patchy skin and dark circles under my eyes. I think I started wearing make up in my late teens. My Mother wore lipstick but very little else.
I wear a light foundation, eyes makeup and lipstick. I am stuck in a rut and wear the same makeup ALL THE TIME ( can I say boring !). I apply a little more eye makeup if it is for a special evening occasion. During the summer I can get away a light power and eye makeup and lipppy, I skip the foundation. Makeup makes me feel more confident,
I scare myself when I look in the mirror first thing in the morning, my skin looks grey.
Clothing, I think I agree with Summer it is balancing act, hiding flaws and enhancing the good. I have never felt particularly pretty but do feel better about myself when I am put together with a nice outfit and makeup, for me they go together.

I have worn makeup since age 14. My mom wore makeup everyday. I wear it because it makes me feel "complete". Most days I go without mascara and lip color, but always foundation, blush, eyeliner, brows, eyeshadow.

Now for my point, i do not like lipstick. I love lip color. To me there is a difference somehow - I love sheer lipcolors that enhance and perfect my look. I want to bring attraction to my entire self and not just my lips. Does that make any sense?

Chiming back in for a moment. I have to laugh a little in recognition of some comments.

What Rachy said about getting a table in the middle of the restaurant -- I hate that! I don't want to be in the middle of the room, especially while eating! I always prefer a booth. Yep, definitely not comfortable being too much the center of attention. Weird for a Leo, right? I only like a certain degree of it -- too much, and I feel like a fraud. I have to fight this feeling when I have something like an art opening, during which I am definitely a center of attention and have to be "on."

However, I am not a wallflower either -- I don't want to be ignored and overlooked! Just not overwhelmed. I suspect this is my extroverted introvert nature. I can see how my style choices parallel this tendency. I love to wear a bold statement piece or two (long printed jacket, interesting boots, great bag, etc), but don't feel at all comfortable in head-to-toe bright color, bold pattern mixes, or silhouettes that are so unusual that they lack some component of flattery.

What a great thread!

And tough questions. Ultimately, I don't believe that I need lipstick or cosmetics to cultivate a better self-image. I grew up with a mother who didn't wear make-up, and a father who didn't like make-up or think it necessary. At the same time, I have always loved make-up from the creative/artistic perspective. So, I own more make-up than I need, but wear it rarely.

I do like dark lipstick on occasion, but part of the reason is that my lips are not my strongest feature, so the colour won't attract undue attention. In truth, a bold lip looks jarring, but sometimes I just need the pop of colour on a dreary day. And, unlike with eye make-up, it's a look that I'll never get used to, and therefore won't feel that I can't leave the house without it.

As wonderful as make-up is, the feminist hippie in me prevails on most days, so I tend to go out bare-faced.

ETA: I have my share of skin flaws, but there's a part of me that resists the "blank canvas"/contoured look. I have pores, scars, and blackheads, but so what? I don't care if a stranger on the street sees that.

This is so very interesting, and I am just overwhelmed by the thoughtfulness and care you have all put into your comments. I don't have time to respond in great detail right now but I have read and will reread each of your comments with great appreciation and try to respond a bit later.

I've got lots of beauty hangups but wearing lipstick comes naturally to me. I wear something on my lips all the time, at home alone or out and about, and I've always touched up my lipstick right before my husband comes home from work, even if I'm wearing yoga pants and a tshirt. I think it's just one of those things I internalized very early - that good grooming includes a little color on your lips. I've been transitioning to a lighter color (I've been a Clinique Black Honey fan for years) and it's hard for me to wear something paler that doesn't show up as much.

This is a really interesting discussion. I think I wear makeup both to highlight and camouflage. Lipstick is the one thing I wear everyday though. My lips are pale and I looked washed out and lifeless without lip color. I'm pretty boring about it though and wear a brownish-pink color that's similar to my natural lip color but darker. I've been thinking about branching out into something a little brighter - more a berry color. I don't wear a lot of eye makeup - just mascara and eye liner because I'm lazy. My eyes are already pretty and don't need much help. I wear a light foundation to even out my skin tone.

Goodness, this ties into Angie's blog post this morning, which I read and responded to first.

I do wear lipstick, but it tends to be subtle...just a hint of color to keep me from looking too pale. I rarely wear makeup anymore, maybe just a hint of concealer, and occasionally an eyeliner, unless I have somewhere special to go. I prefer to focus on keeping my skin clear and healthy, and I have developed a sensitivity to some products so that's made it easier to avoid makeup. However, to answer your question, it's definitely a balance, even with clothing, to downplay what I consider the negative and yet accentuate the positive (yet not too much ;-)...tying this in to Angie's post about environmental norms!). I don't really like attention, but I do want to fit in, be appropriate for the occasion, and be true to myself. As I said in the blog comments, it's definitely a work in progress.

And Shevia, your dramatic coloring works wonderfully with lip color. I have similar coloring (but dye my hair) and I can carry off a bold lipcolor but often choose not to. You too could wear a less-bold color and maybe that would feel more authentic and less "look at me" to you. I like Burts Bees for daily wear. It's more a tinted Chapstick than a full-on lipstick.

Shevia, thanks so much for starting this thread. You are so stunning, and I would suggest your eyes don't need a stitch of makeup to steal centre stage anyways. Thanks for sharing your story, and everyone else too!

Re: makeup, I have always loved it; to me, it's a bit like my watch or wedding ring - I just don't feel quite dressed without it.

As to holding myself back, here's my struggle: I was raised by parents who were fairly near the bottom in their respective socio-economic contexts - as far as I can tell, my mom responded by trying to minimize herself, while my dad took a more "screw you then" approach, but neither, I don't think, had a sense of quite fitting in, and this was passed on to my sister and I. For example, I remember asking my parents for a cool brand of shoes when I was a kid, and my younger sister saying, those shoes aren't for US, they are for [insert name of wealthy kid from school]. Fast-forward to today, I am quite a confident person but still have this feeling of not being quite right, so this can translate into timidity with my style. If you remember the show "The Nanny", there is a line in the theme song where they say "She's the lady in red, when eveybody else is wearing tan". I tend to wear tan even when I might prefer red, if that makes sense. But I am working on it!!

xx

Forgot to say, Lara, your mom was very elegant! A beautiful lady.

And I too aspire to a bit of Caro's confident and ease!

I'm like Style Fan - I love makeup but try to go for a natural look with it. I don't wear red lipstick but I do wear lipstick most every day - nudes for me most of the time unless I'm trying to look dressed up. I don't think I try to camouflage too much, but maybe I do with adding eyebrow pencil to "fix" thinning brows. And if I didn't wear mascara, my lashes would be pretty light. I like a little foundation to even things out I guess. All that said, I can go without makeup and most people don't seem to notice so I guess it's not a major difference.

I do camoflage my hair - if I let it go natural it would be very "messy" wavy, all over the place so I tame it into a style. I feel weird if my hair is too big.

Shevia, given that you are a style inspiration for me - clothes, hair, attitude - I had to ponder overnight before responding.

Lipstick is often my only makeup, given that I have pretty bold features. I just sorted out my collection into a three drawer plastic container: purples/pinks, reds, and nude/browns. That's how many I have!

As far as self-image, growing up I was much like you, and in addition a minority up through high school. No one else looked like me, and I never felt pretty or attractive. I was labeled as the quiet, smart one besides my stunning, outgoing sister (who of course is brilliant as well!). It wasn't till my early 30s that I developed some real confidence and ownership in how I look, and that timing coincided with the ideal of beauty in the US shifting to a slightly more diverse one - Tyra Banks, Naomi Campbell, and other prominent women of color in the fashion industry.

Today, having embraced who I am and how I look at (about to turn) 50, grey hair and all, I seem to get more attention and compliments than I ever did when I was younger and striving to be pretty. I don't think is because I look better objectively - it's because I am more comfortable in my own skin, and that must be attractive to others somehow. I dress for how it makes me feel, rather than downplaying or playing up features. I try to be aware of when something is genuinely unflattering, and that's about it.

I sometimes wonder if people who think someone is gorgeous hold back from saying so because they assume the person knows or is told so all the time. Back when DH was first smitten with me, I couldn't believe he found me as beautiful as he claimed - no one had ever said those things to me before. In my head, I was still fixated on everything I'd never be.... tall, blonde, leggy, willowy, graceful. But from his perspective, I was this exotic beauty completely out of his reach. Go figure!

This is why I go out of my way to compliment people, be they friends and strangers. What you see as an outsider may have nothing to do with what's going on inside.

You are quite stunning and your joie de vivre, wit and humor shines through halfway around the world!

I completely misinterpreted your appearance!

Your description of the internal factors determining which beauty products you use came as a surprise because I thought your cosmetic look was about not muddling natural beauty, which you definitely have.

Your eyes are lovely but your mouth is very expressive and lovely too.

I have been so moved by the responses to this thread. So many similar experiences, funny stories, resonating thoughts, I am floored and overwhelmed. Wow. Angie I am sending you a huge hug and hope you take great pride in the wonderful community you and Greg created here.

I know I am not expected to respond to every one of you but you have said so many wise and helpful things I want to try to highlight some.

MsMaven you and other commenters have what seem to me a healthy relationship with makeup.
Aziraphale we have not seen much of you, but what I have seen tells me that you are more exceptional than you will admit. I think the lesson of this thread, or maybe the lesson for me, is what is wrong with playing up our strengths?
Staysfit You naturally see makeup as an extension of your role, or maybe a tool to make you more effective, and that makes a lot of sense given your profession. I think you are right that makeup looks right when it suits the personality as well as the features of the person.
Angie, what can we say, we Cancers are very emotion driven even when we can be quite rational in our behaviour. Rational means to satisfy our emotional drives for the win!
I did love Beth Ann's comment also.
Astrid you remind me very much of younger me. I also did not want to create expectations or subscribe to societal norms of how I "should look". I wonder how you will feel in a few decades :).
Rachy I find left field a perfectly normal place to float. And I also somehow see lipstick as more a style statement than other kinds of makeup. I hate sitting in the middle of the restaurant, but will sit on the side wearing a strange outfit. I was definitely not raised to consider my looks a tradeable asset, hmm.
Diane you are a true sweetheart. I am adding you to the healthy attitude group!
Style Fan you have what I think of as a healthy, balanced attitude toward makeup.
Bijou Sounds like you had a great role model!
gryffin Ha! Surgar Fresh in Rose was my lipstick gateway drug. Mind forged manacles is startlingly to the point.
La Pedestrienne It does seem that maternal role models play a huge role. I am thinking about the relationship to performing.
Aliona I do think there is a strong connection between grey hair and lipstick - yes it helps brighten you up, but for me I think it is also a counter to some sort of vanity that I think I wrongly connect to lipstick.
Archer, thank you for fail bright women. Hits home. Yes I do also wonder if it is not a bit of inverted snobbery gone sour.
Summer, that's it. There is a value on humility, but I think it goes to far with lots of women.
Windchime, I feel that it is a sign of healthy self esteem to try to counteract low feelings by dressing up rather than laying low (as I sometimes do).
bettycrocker Do you wear eye makeup?
Janet Oh boy (uh, girl) did I relate to what you said. Pride and low self-esteem are more connected than I realized in me.
Ginger I love that you found your self in vintage style. I would be delighted to see more of your looks.
Gail I challenge you to wear a completely new color lipstick!
Lara Your mom was stunning. My grandmother died at 95 with her lipstick still perfect. I don't think it matters if it is lipstick or another product if it makes you feel yourself.
gradfashionista Mothers have a huge role in this. And there is that feminist hippie thing. Yes.
Thirkellgirl I am guessing your mother also wore lipstick? You seem to have that natural attitude.
Sara L. You, including your eyes, are very pretty. I suppose I think the same thing about my eyes, but why not play them up?
Aquamarine A work in progress and a balancing act. Thank you for your comments. You know I never thought of myself as dramatic looking until quite recently - it was a revelation.
torontogirl I wish my sister still lived in TO so I could come over and hug you next time I visited her. You are a gorgeous woman and you should wear red whenever you want!
texstyle No need to wear red lipstick if you don't want to - like Style Fan you seem to have a very natural attitude to go along with your natural look.
Una as you may have noticed, I have decided we have a lot in common (not just turning 50 this year and already claiming it). One of my oldest and best friends comes from a Pakistani family and grew up in New York with a lot of the same feelings and experiences you describe. Couldn't agree with you more about complimenting people and never knowing what is going on in the inside. We are long overdue to meet imho.
Isabel what a lovely thing to say!

Shevia, it is very classy of you to take the time to respond to each and every one of us.

As for your question "what is wrong with playing up our strengths?" -- absolutely nothing, of course. Regarding myself, I guess I was just saying that I have no exceptionally "good" features, but the whole package is not bad, and I dress/wear makeup to enhance the "better" aspects of my face and figure. (Usually. Sometimes I wear stuff that I know is not my best look).

I want to add that I don't feel like it's "cheating" to use makeup to play up the features you like. This idea of cheating comes up more often in relation to makeup than to clothes, perhaps because women wear it and men/children don't. I think the root of this attitude is the whole "painted Jezebel" Bible thing that made makeup completely off-limits for "respectable" women during the more Puritanical phases of Western civilization. But how is mascara and lipstick any different than wearing heels? We all know that heels make your legs look fantastic, and no one's going to accuse you of cheating for wearing them. Same goes for dressing for figure flattery. Makeup is just another way to work with what you've got.

But this thread is really about self-esteem and how we present ourselves to the world. The real issue is the fine line that women in particular have to walk in the public sphere. We are judged on appearance, and if we overdo it, we risk being dismissed as a show off (or worse). But no woman relishes the idea of being invisible, either.

It's kind of like how an assertive woman is more readily labeled as "bitchy", whereas a similarly assertive man is just seen as confident.

ETA For me, it doesn't take self-esteem to wear lipstick. It's the opposite. Lipstick improves my confidence. Without it, my colourless lips just blend into my face!

I didn't comment earlier because I am still in the throes of thought. You raised some very important issues that I want to think more about.

A few things.
I love lipstick. I buy a new lipstick every time I am sad or disappointed in life. The more sad I am the more red the lipstick.

IRL I wear a very moisturizing product called "Sugar." It is subtle, but fits my internal image. The red lipstick I buy so much of does not fit my internal image. It is hard to wear because it takes so long to get it right.

I too thought it was very classy of you to respond to every poster.

This is a really interesting thread Shevia. Like you as a young woman I thought more about brains than beauty, and my makeup at that stage was minimal, a soft lipstick and mascara once in a while. Growing older I never did get on the beauty products train. Just as well, I'm a hopeless klutz when it comes to hair or beauty. But I always wear some light makeup, usually a touch of concealer ( darn those dark circles! ), blush, lipstick and eye liner. The whole thing takes under 2 minutes and I think it's a "natural me". I guess it functions both to enhance the good bits and to minimize the not so good. Revenue neutral so to speak haha. And I suppose that's the way I look at dressing too. I don't know what all of this really says about self esteem - maybe it's more about self awareness?

No, you don't need a positive self-image to wear lipstick. Some people who wears noticeable things might hate themselves and hide behind their clothes, who knows, or they believe in the magic of red lipstick and feel more confident with it.
OTOH, you didn't strike me as an insecure person, with ou without lipstick.
I don't associate bold appearance and self-confidence.

I don't dress to highlight or camouflage and I'm tired of the idea that I should be the best version of myself or unleash some hidden potential.
My only challenge when I dress is not very challenging : I have a short waist, and feel about it exactly as Rachylou does.
In general, I have trouble making the distinction between flattery and fit, they're the same to me.

As for getting attention : I don't have the energy to deal with it. I barely have the energy to say hello in the morning, let alone discussing my fashion choices

I started wearing tinted moisturizer and mascara in my 30's and only wore chapstick until I could no longer wear my contacts and had to wear glasses. I need thick lens therefore a heavier frame to balance. I found I need a darker lip to balance my face. It was a hard adjustment for me because most lipstick tastes terrible, imo. After a drawer full of lipstick I would no wear I finally tried channel. No bad taste. I still have trouble with the darker shades, though and I know it must be psychological.

Shevia, I wear eyeliner (top lid only) and mascara. That's all the eye makeup I wear. My reason for not wearing lipstick most of the time has to do with the hassle of having to reapply it every time I turn around. If it weren't for that, I'd probably wear it every day. The long-wearing lipsticks are drying, and I strongly dislike that.

I am enjoying this fascinating thread. I have enjoyed all the responses - what an interesting honest intelligent group of women!

I do wear lipstick (and makeup) most of the time. It makes me feel more together and polished and less tired.... I tend to wear either a rosy/nude colour or a bright red the most - and I do have to be in the right mood for the red.

I have changed as I have grown older. I was very "natural" during my university, travelling and early working days. I particularly disliked men reacting to my looks and not my character or intelligence. However what felt right at 20 or even 30 does not feel right at 45 and I feel more professional, confident and attractive with a little more effort now. Because I am a little lazy I sometimes do not wear makeup or leave the house with washed but wet hair. I tend to regret it. I happily go to the gym without makeup or wear my swimsuit in front of most people, but for my general daily life I now prefer to have better presentation.

I also love diversity and I have a friend who is known for her bold lipstick as she fiercely mountain bikes, and I have other friends who rarely wear makeup, nor colour their hair or blowdry it. All of them are beautiful to me.

Fascinating thread!

So much of what you've said, Shevia, hits home for me, especially the scorn my family and friends heaped on woman who used their appearance as a "tradeable commodity" . Appearance didn't factor into my world until I became a reasonably attractive teenager. I was disconcerted when people paid attention to my appearance and tried to sweep it aside. Playing sports and concentrating on academics put the focus back where it "belonged".

Thinking about it now, I guess I've never worn anything but the nudest of lipstick because I always preferred to work alongside males as a colleague, not a female. The few times I did use my appearance as a "commodity", I felt powerless instead of powerful.--red lipstick as a downer instead of an uplifter? Growing older, letting my hair go gray, and developing a thickening body are oddly comforting because I don't have to deal with the "appearance thing" anymore. I can play with fashion and red lips without feeling like I'm putting the focus on the wrong part of who I am as a person.

What i find interesting about this is that sometimes a positive image can be cultivated be wearing lipstick, instead of the other way around - building on the 'act the way you want to feel' phenomenon.

My self esteem has had peaks and valleys, and as I thought about this question, I realized that I hadn't given thought to my best features for a while and had been dressing without those in mind, and might have been unintentionally feeding a lesser image of myself. For example, I had been wearing lip balm mostly until about a year ago, when I decided to wear a brighter lipstick and love the look (and actually noticed that I liked my lips.) When I looked in the mirror, I realized that I loved my legs and arms, but never dress to show them off, even in summer - though I know that would make me feel happier about myself. Actually noticing my best features (instead of just focusing on the faults) has been key for me. Have resolved to show them off more!