Reader Request: Age-appropriate Dressing

Loose guidelines for age-appropriate dressing

Many of you have requested some guidelines for dressing to suit your chronological age and although I’ve touched on some loose guidelines for women over 40, I wanted to address this topic from a more general standpoint.

But first, the caveats:

There are about a billion guides to age-appropriate dressing out there, and I know that many of them have proven invaluable to many women. I’m not a huge fan of such guides because they leave so little room for individuality and variation. Like all sets of rules, they are rigid and inflexible and assume a lot about bodies, goals, and needs. I don’t believe that fat women should never wear formfitting clothes, I don’t believe that short women should never wear long skirts, and I don’t believe that women of ANY age should be automatically excluded from any garments or styles. We are informed adults who know our figures. We can make those calls on an individual basis.

That said, many women are interested in understanding the rules so that they may bend and break them on a rule-by-rule basis. Many women would rather stay within the common parameters for age-appropriate dressing for their own comfort. Many women are just curious about these norms and guidelines.

But instead of parroting the socially-accepted rules, I’m going to present a different way of looking at age-appropriate dressing. I realize that many of you think all age-related dressing guidelines are total bunk, and that’s just fine. But I have been absolutely inundated with requests for my input on this topic, so I know that many of you are quite curious …


How you present your figure, which aspects you choose to highlight, and which garments make you feel confident and comfortable are ALL influenced by age. And relating your age to your wardrobe choices can help you build an ideal, highly personalized style.

But how a woman looks, feels, and behaves may make her seem decades older or younger than the date on her birth certificate. And although some experts believe that chronological age should shape certain aspects of life, I’m willing to assert that internal age is considerably more important and influential. Especially when it comes to matters of style.

All style rules are simply guidelines, but I think that edicts about age-appropriateness are the most guideline-y of all. No one over forty should wear a miniskirt? Seriously? Have you SEEN Madonna? Pearls are the exclusive domain of aged grannies? Rihanna and Nicole Kidman would beg to differ. Of course, exceptions to these rigid, age-based fashion rules aren’t all celebrities. In my opinion, any woman who feels confident, beautiful, and wholly herself in a certain garment should wear it, regardless of age.


So all this makes you the ultimate judge of what works for a woman at your age. Try not to get drunk on your own power, OK?

Now, if you loathe all age-based rules, you quite possibly loathe socially-centered dressing norms and shun edicts about the comfort of the observing world. And the following will simply rankle you. But if you have concerns about dressing your age, you may also want to consider context and audience when you mull matters of age-appropriateness. If you fall into the latter category, here are some questions you should ask if you’re ever in doubt:

Do your friends and peers wear it, and wear it well? Your peer group may include women whose styles are vastly different from your own, but use your imagination. Can you imagine a similarly-aged coworker donning this outfit? How would you feel if you saw a woman your age wearing it and didn’t know a thing about her?

If it’s outside what your age group normally wears, why do you want to wear it yourself? I don’t believe in hard-and-fast rules of age-appropriateness, but I do believe that some women dress to appear older or younger than they truly are. Sometimes it works, sometimes it fails. And when it fails, it can fail SPECTACULARLY. So examine your motivations carefully. If no one else your age would consider wearing this, why is it important that you break new ground? Are you trying to disguise your age, or fool the observing world somehow? Do you simply love it and not care about any potential peer judgment? Are you trying to recapture a time gone by?

Does it make you feel fabulous about your body? If you’re 57 and have amazing legs, there’s no reason to hide them under long skirts. If you’re 19 and feel best when well covered, don’t let anyone pressure you into overexposure. Clothes were invented to cover our privates and keep us warm, but clothes exist in variety to help us feel awesome about our bodies. And clothes that make you feel awesome about your body should be worn. By you.

Where will you be wearing it? A 38-year-old in a babydoll dress at an outdoor concert will blend right in. A 38-year-old in a babydoll dress at a corporate conference will raise eyebrows. A 22-year-old in a tweed suit interviewing for a job will pass muster. A 22-year-old in a tweed suit at a kegger will stick out like a sore thumb. You may not care to conform to age-based fashion norms, but they still exist and you probably have a decent idea of what the big ones are. If you’re going to subvert them, make sure that doing so won’t cause you undue discomfort or attract unwanted attention.

Who will be there, and whose judgment are you considering? The most important consideration in dressing outside typical age boundaries is judgment. If you are a sensitive soul who can’t stomach criticism, bend those boundaries only when you’re spending time with trusted friends. If you couldn’t give a flying rat’s ankle what ANYONE thinks about you, wear anything whenever. Use your head, of course, and avoid jeopardizing your job and offending important officials. But otherwise, anything goes.

Most age-appropriate rules revolve around older women dressing “too young,” but some younger women have concerns about dressing “too old” AND “too young.” I feel that these flexible, reflective questions can aid women in either situation.

Again, these questions and considerations will only be useful to those who want to dress and feel age-appropriate, and avoid incurring any potential negative judgment. I admire women who shun age-related norms and women who embrace them quite equally, and don’t believe that either philosophy of dressing is superior. And, again, these are mere guidelines. Nothing here is gospel, simply a set of ideas about how to address age-based dressing concerns.

Image courtesy Boden

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details. Sustainable options are either used, handmade, made in the U.S., artisan made in non-sweatshop conditions, or made using sustainable/fair trade practices.

Originally posted 2010-10-19 05:02:00.

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50 Responses to “Reader Request: Age-appropriate Dressing”

  1. Rebekah

    Great post! It's a delicate subject, but you've covered it very well.

    I'm 25, but I don't feel as "cute" as a lot of girls my age, and I dislike a lot of current styles. Consequently, I have to watch myself to avoid dressing ten years older than I am.

    There are lots of looks geared specifically toward teenagers and middle-aged women. Sometimes it's hard to know how to dress between those two stages.

  2. Frankincensy

    I found it thoughtful and helpful as always!

    My two cents: I'm 21, and the fashion industry expects girls my age to be comfortable with showing a lot of skin. In young/trendy brands (which tend to be the only ones that fit me), it's hard for me to find shorts with more than a 3" inseam, or skirts that come past mid-thigh. I don't have moral or religious qualms about revealing clothes; it's about 60% body image issues (which I'm working on) and 40% personal taste. I'm happier in long sleeves, skirts a few inches above the knee at most, and tops that don't cling, which can make shopping difficult sometimes.

    Happily, I found out about alternative street fashions through the FRUITS Magazine photobooks and style blogs like Hel Looks. This taught me that my more covered-up style could be elegant and interesting, not dowdy. Browsing fashion history books gave me a lot of inspiration, too. I do sometimes feel pressure to fit in with my peers a bit more, but I'm learning to reconcile this with my own sense of style. It helps a lot that looser-fitting clothes and vintage-inspired looks have been trendy recently.

    As far as clothes go, I am incredibly glad to be 21 instead of 16-17. I have more confidence now, and I feel like I can pull off the more elegant or grown-up styles I love without looking like I'm playing dress-up.

  3. Anonymous

    If you dress to flatter your body, I think you pretty much can't go wrong. I am in my early 50's and I pretty much wear the same styles as I did in my 20's; they have passed the test of time in terms of working well on my body. I think there are nuances that play into the "too old" and "too young" thing, though. One is color: some colors are sort of of-the-moment and as such, are very "young" (and maybe too young for some settings) whereas one could wear the same garment in a very trendy style but in a more subdued color and and it would be viewed as tasteful on any age woman. I also think that where one lives has something to do with young/old standards of dressing. Here in northern California, I think dressing nicely in any way can ironically project a younger OR and older image because you stand out. Dressing ultra casually has become a sort of default position and if you dress stylishly, you are inviting an analysis of age-appropriateness of your image, no matter what your age.

  4. Elly

    I really enjoy how you get readers to question WHY they dress the way they do, or want to: sometimes clothes/fashion are considered as fripperies but often dictate more about our personal and social positions to others (and ourselves) than we are prepared to acknowledge. So hooray for thinking!

    I feel very much the same way as Rebekah and Frankincensy; I'm 23, now a post-graduate student, and recently had a bit of a difficult time identifying how I wanted to dress. It was a case of realising that I wasn't the same person inside as I was 5 years (or maybe even a year!) ago. I wanted to be more 'professional' without losing any fun or individuality. I agree with the youth/exposure connection that can be a bit disheartening (both from a practical and a political perspective) and the difficulty of dressing for the 'between' stage of teenager/young adult and professional grownup. It's not a case of stopping wearing certain clothes (eg short skirts or really on-trend garments) but appreciating a new range of clothing that several years ago you wouldn't have even considered, like beautifully tailored coats, or lower-heeled but still gorgeous shoes.

    I think the comment from 'Anonymous' is very interesting, about dressing ultra casually becoming a default position. With this, and the fact that retailers sell clothes to all different ages, worn by all different ages, casual clothing doesn't invite (as Anonymous says) any judgement on age because you're used to seeing a whole spectrum of ages in that style. Dressing 'nicely' – I might say 'formally', or even just 'non casual' – can look so out of the ordinary in a sea of casuals that your appearance is critiqued even more closely!

  5. eek

    Excellent post. This subject is something I think about a lot, as I am approaching 40 (aack!) but still feel like I should be in my 20s. Most of the time I buy what I like and what makes me feel good, but I think I am attracted to cute-sy stuff, and I do my best not to look like a person-trying-to-look-younger-than-she-is. I just want to look cool, you know 😉

  6. LK

    Its helpful to be sure. I'm 26 and my problem is Im still built like I'm 18. I can rarely find clothing that fits me outside of the juniors department. For me, its really hard to dress my age simply because I can't find anything in the adult clothes that fits.

    That often seems to be some people's issues. They can't find clothes for their age group that fits them because they are not of the norm in body type for their age.

  7. Sarah Eagle

    This is certainly an interesting topic, especially considering a conversation I had with my boyfriend over the summer. I'm 23 and I work in a pretty casual environment (jeans are really expected at this point) but I've always tried to cultivate my own personal style. However, when I was dressing at some point over the summer for some function or other my boyfriend complained that I didn't own anything "sexy" or at least age appropriately sexy.

    For whatever reason, I've always gravitated towards skirts that hit just above the knee (I'm short 5'3" and longer skirts usually just look dowdy on me). In many cases, I like a nipped in waist, either through a belt or the dress itself. It's a style that I feel comfortable in and feel comfortable wearing to work (keeping in mind that I work in a mostly older male environment and I would never want to appear "sexy," "young" or overly "girly" in any way, it would just make me feel uncomfortable).

    In either case, its funny because I've learned to like my body and I'm slowly beginning to see what it really looks like as opposed to my warped vision of it. But, still, I look through magazines and see what 20-somethings are supposed to be wearing and it would just make me feel uncomfortable. The styles seem to be gunning for 20-something women who are much taller, with longer legs than I. So, instead, I run the risk of seemingly dressing too old

  8. Sheila

    What an awesome post, Sal! I love how you framed this issue with questions, rather than just spitting out the same ol' rules (this 43-year-old is wearing a mini skirt and thigh-high boots today, thankyouverymuch). That you put the onus on us to determine, based on great questions, how we feel about what we're wearing is sheer genius.

    This is why you are the best blog out there.

  9. Casey

    Very interesting post, Sally, and I've enjoyed reading through all the insightful comments thus far!

    I have to admit I've always been attracted to what are considered "older" styles (whether my "granny chic" admiration of the 1940s, or less youthful/less revealing styles than are marketed towards my age group). Minis and super revealing/trendy clothes, which you're kind of "expected" to wear as a teen/twenty-something, have never appealed; I prefer to be a bit more covered up (mostly personal preference at this point). I've always thought I dress older, and must therefore look older. But imagine my amusement that most people still peg me for younger than I am (right now the going age is 22ish; I'm 25). I think a lot has to do with my baby face, how I carry myself and approach things.

    I also have become more aware that as my face and body have matured/changed a bit over the past two years, I've been able to move towards wearing more sophisticated garments and actually pulling them off with some aplomb. When I was younger I couldn't; I just looked like a girl in a woman's outfit, trying to be something I wasn't! (So some things were definitely not age-appropriate.) I've had to tweak a bit how I dress more recently as I've hit my mid 20s (for instance I have started to shy away from clothes that are too "precious" or cute; I feel that they no longer really jive with how I feel or approach fashion!), but essentially I still go with what makes me feel good and is appropriate. I hope I'll continue with that through middle age and beyond; I want to be one of those amazing older ladies who has a fantastic sense of personal style, but still is age/situation appropriate!

    ♥ Casey | blog

  10. LandTitanic

    I definitely agree that dressing the age you FEEL is more important than dressing the age you are. Somedays I'm feeling older (I'm 26) and I'll dress in more mature clothes and feel totally comfortable but other days the same outfit feels uncomfortable and wrong.
    I also have problems with shopping in department stores. It seems like the clothing goes from juniors to clothes my mom would wear. I think that's why I spend so much time shopping in thrift stores (plus they're so much fun).

  11. tinyjunco

    this is a rough one to tackle. i think you did a good job of putting all the qualifiers out front, Sal! standards on 'appropriate dressing' generally are just so all over the place these days. your advice on comparing yourself to others in your cohort (age, profession, region) is a good rule of thumb for finding what's appropriate in your situation. anon's comment that subdued, classic colors will be seen as more appropriate for older ladies also holds true.

    on the average, as an around 50 year old lady, i'd say that more skin showing, tighter clothes, exaggerated shapes, brighter/trendier colors, trendy or faddish shapes/accessories tends to read younger.

    classic/neutral/subdued colors, good fit (not too loose, not too tite, no exaggerated shapes), quality materials (pure fibers, nicely finished leather, linings, pearls, gold platinum silver, semi-or precious stones), less skin showing, classic (as opposed to trendy or faddish) shapes and accessories tend to read older.

    but A LOT depends on region, culture, lifestyle, profession….Advanced Style is a great blog to check out, because so many of the people featured have honed their style over decades and decades. it really shows how little age has to do with style (except for the opportunity age allows for accumulation of experience and fabulous jewelry).

  12. Diana

    Interesting post… I'm not really one to fret over being age-appropriate. I mean, I won't dress like most teenagers or my grandma, but everything else is OK. (Hey, I know some really stylish grandmas!) I think you have touched on a couple of big things to consider though, such as context, but I'm not really sure it's totally about age-appropriateness… ANYONE wearing a babydoll dress to a corporate event is inappropriate, whether they are 40 or 20; it's just that you're much more likely to be going to those events if you're 40.

    I think the most important thing by far is that you're comfortable in your clothes, and if that means dressing your age or not, then so be it.

  13. Anonymous

    Great post! Oh, dear, I'm 63 and still wear roughly the same clothes as always: tailored, plain, lots of colour on a black and neutrals base, details and jewellery. Over the years, my hems have gone up and down, pants widened and narrowed, but the look has always been about the same, what used to be called American sportswear or now business casual. I don't look stuffy or too young, and I never looked too old before, either. There are years when I can't buy anything as it's all the wrong colour or cut for me. It's less of a problem because I sew.

    The first pic of the woman in the black outfit is a look I've seen in the 60s, 70s, 80s (with shoulders!), 90s and still works. It's also my style.

  14. Jingle Bella

    Great post! I think another factor to consider quite seriously is geographical area – I've noticed that when I'm on holiday or off in a big city I'm more adventurous in my dressing than when I'm at home.

    For example, something that wouldn't make anyone blink in NYC might make you stand out and feel awkward in a more rural area.

  15. Anonymous

    P.S., I'd also wear the white suit with those great shoes! But not the suit with the boater hat. No, that's great on the model, but stuffy granny on me.

  16. ang

    Age appropriate dressing is such a sensitive topic and I have written about it many times. As a professional fashion stylist I have many clients over 40 – and I am 40 too. I deal with age appropriate dressing concepts daily. It’s a biggie and often a judgment call on my part.

    I wholeheartedly believe in the concept of age appropriate dressing and am a little stricter than you are, Sally – even though I appreciate how carefully you are treading on this subject, making women feel liberated and uninhibited straight off the bat. I do think it’s inappropriate to be wearing things too short, too tight and too low after a certain age. Of course, the BIG question is how short is too short? How low is too low? How tight is too tight? And how old is after a certain age? But at the same time I encourage the wearing of hip fashion trends at all ages because effective execution is everything. Forget about your age and concentrate on effective execution. If you read my blog and ask my clients – well, their actions speak louder than my words! It’s all in the HOW and the details of the outfit. Amp up the sophistication as you get older and you’ll get away with wearing a lot more!

    Fab post!

  17. angie

    Age appropriate dressing is such a sensitive topic and I have written about it many times. As a professional fashion stylist I have many clients over 40 – and I am 40 too. I deal with age appropriate dressing concepts daily and it’s a biggie and often a judgment call on my part.

    I wholeheartedly believe in the concept of age appropriate dressing and am a little stricter than you are, Sally – even though I appreciate how carefully you are treading on this subject, making women feel liberated and uninhibited. I do think it’s inappropriate to be wearing things too short, too tight and too low after a certain age. Of course, the BIG question is how short is too short? How low is too low? How tight is too tight? And how old is after a certain age? But at the same time I encourage the wearing of hip fashion trends at all ages because effective execution is everything. Forget about your age and concentrate on execution. If you read my blog and ask my clients – well, their actions speak louder than my words! It’s all in the HOW and the details of the outfit. Amp up the sophistication as you get older and you’ll get away with wearing a lot more!

    Great post!

  18. no more frump

    Hi, I've seen your name over at Style Underdog's blog. What a great post! This is such a great topic. I am striving to dress to flatter my 41 year old body and I do struggle with what is too young or too old.

  19. leah

    I kinda sometimes feel like I am a bit too old to be wearing hair bows and neon hi-top sneakers. Then I suck it up and realise that nobody really cares. They make me happy so I wear them.
    I applaud you challenging the idea of "age-appropriateness" Sal, like women are supposed to stop having fun with clothing and start being sophisticated sportswear bores once they hit 40. Boo to that I say. Occasion-appropriate dressing is useful (it's just good manners I say), but age-appropriate is just another way to make women feel insecure about ageing.

  20. rb

    I feel like I've been dressing like I'm 40 since I was about 22, and now I'm 45 adn I'm still dressing like I'm 40. This is for two reasons – one, I've always wanted to be taken seriously at work, and two, the styles I gravitate toward are "classic."

    I love to see an older woman dressed in a fun, funky outfit, but I feel uncomfortable when I see a woman slightly older than me trying to dress in very young, very low-cut, or very tight clothing. I know you had a post on this the other day, and it's not my place to judge, but that is my basic reaction and I'll own it. I always liked it when Stacy London would tell her older clients, "Don't try to dress like a 20 year old, because the 20 year old will always win."

    • tothineownself

      I always think it’s weird that as women we should feel that dressing in a way that expresses who we are is somehow competing with someone else. “Don’t try to dress like a 20-year-old because the 20-year-old will always win?” Win WHAT????

  21. Jasmine

    Excellent post. I like the points you are making.

    I work in software industry. The environment is very casual, and men to women ratio is like 8 to 1. So I try to blend in wearing simple tshirts, sweaters and jeans most of the time except for some business meetings.

    My question is can you pair jeans with a shirt or blazer for business casual occasion? I know traditionally business casual means no jeans, but now days jeans are more accepted? And I love the look with jeans and a sharp blazer.

    Sally, I also sent you an email from Please check and let me know. Thanks.

  22. Anonymous

    Thank you! Your questions were right on target and have given me lots to think about. I don't want to look dowdy, and I don't want to look like I am pathetically trying too hard. I want to look fabulous, I want to have fun with my clothes, and I want to look like me.

    Something that's helped me: when I question the appropriateness of an outfit, I take a picture. Somehow, I can see myself more objectively in a photograph than in a mirror.

  23. Candice Virginia

    This post is so interesting and well done!

    I'm 23. I find that lately, I am extremely interested in cultivating my accessory collection. I wear a nice watch, an heirloom ring and usually a brooch or pretty earrings from etsy every day. I am drawn to jewelry because it allows me to express myself without worrying about fit or function (for the most part). This is new to me and I am enjoying it a lot.

    With clothing, each year I reflect on my style development and find a slight shift towards something more classic and simple. I like dark wash jeans, sweaters with pretty detail, crisp white shirts and simple tennis shoes or boots. I like to look clean cut and wash-and-go.

    This is a pretty dramatic shift from the short dresses and tank tops of years past. I think I'm just finally getting to a place where I can successfully shrug off the societal pressure to look "hot" or "sexy." I always knew I prefered a more refined look, I just didn't know how to balance it with the expectations around me.

  24. Sara

    Great post. It's all about comfort and personal style for me. If I dress to flatter my figure, it shouldn't matter how old or young I am. Like you said, a babydoll dress in the conference room will always be inapropriate, no matter what the age of the person wearing it is. I think for some people there is this unwritten rule that once you hit a certain age or once you become a mom, you are supposed to lose your sense of style. I just don't subscribe to that. Honestly, at 30, I am probably more stylish now than I was at 20. I have had time and life experience to learn what I like, what flatters my body and what makes me feel comfortable and beautiful. I'm not going to change that as I get older just because some of society thinks I should.

    In response to a family member of mine wearing a bikini on vacation, my dad said to me that he doesn't think women over 30 should wear bikini's. "They're just too old," he said. I couldn't disagree with him more. First of all what does he know about one- and two-piece bathing suits. I'm long-torsoed, I can't wear a one-piece and look nice. Not possible. And just because a woman is over 30 should have nothing to do with her bathing suit choice. Be comfortable and be happy, who cares what other people (usually people with no frame of reference anyway) think.

  25. Subliminal Sumenal

    Great post! As a 40-something woman, I certainly don't dress like I used to in my 20s though I think it's because I was experimenting. Now, I know what I like and what I feel good in, so that is what I wear. I don't much believe in the "don't wear this or that after 40" rules. I admire women who wear what they wear with confidence whether they are 20, 40 or 60. Who follow their own rules and who feel fabulous in their own skin. As my daughter would say: "Girl Power all the way!"

  26. angie

    I am concerned about my age and the way I dress.Iam a bit over 40 and I want to look my age.I didn;t spend so many years to refine my style only to mess it up in my 40s!

  27. Ivy

    I'm in a weird place–I'm 27 and where I live the fashion for my age tends to be casual. I could live my life in jeans and hoodies or sweaters (even at work) and nobody would bat an eye.

    But I'm working on branching out into cute dresses, tops, skirts, etc. that are funky or girly enough to not look too corporate, which seems to be what really stands out.

    Cultivating a bit of an air of the slightly odd girl helps too. 🙂

  28. RoseAG

    Jasmin – yes you can pair a jacket or blazer with jeans for a business casual look.

    In fact, my rule is that anytime you wear jeans to work you should have a jacket with you. You never know when a client or big boss will arrive and you'll want to look professional and competent.

    It's good for a gal in a male-dominated business like software to have the extra authority that a jacket gives a casual outfit.

    If it's too much to drag a jacket back and forth pick up something decent, it can come from the clearance rack at Old Navy if need be, that goes with jeans and leave it hanging in your cube all the time. When opportunity calls you'll be ready.

  29. Anonymous

    Hi Sal –

    I am over 40 and I have to buy a black dress to stand up in my mom's wedding next month. I've gained a ton of weight in the past few years and I have not bought or worn a nice dress since. In grad school for 3 years, all I wear is jeans and T-shirts.

    So I went looking and I did not want anything that was sleeveless or showed my upper arms. But every black cocktail dress with sleeves looked matronly, very mother-of-the-bride. Very "over 40".

    After an hour of looking online for plus sized black cocktail dresses that did not require me to have a waist when I lost it along with my 30s, and that covers the arms, I am pretty traumatized. I just went and bought a bag of M&Ms and I don't even like M&Ms.

    So your post resonates with me because what do you do when all the stuff you LIKE only looks good on younger – thinner – other women with a very different body shape from your own, and all the shapes and styles that might flatter your own age – size – etc look ugly and old to you.

    It's a pickle.


  30. Anonymous

    I'm 56 and find that getting dressed is much more complicated than it was when I was younger. On top of everything else to consider for myself, now I have to throw in the curve ball of whether it is age appropriate. Just when you think you have your style figured out, it doesn't work anymore. I guess it is an evolution, but it seems to happen overnight.
    One of my gauges is to think about people seeing me from the back and getting an empression that I am younger than I am, then I turn around and they would be a bit stunned to see that my face shows my real age. I know I would be humiliated if I were in that scenerio so I try to look as modest as I feel.

  31. LPC

    It's' funny, lately I've had a different sort of problem. I'm 54. I'm OK with dressing with more dignity now. I don't have big issues with my body, it's within weight range etc. But things are flabbier and shifted. I don't feel like flaunting that. When I tell salespeople that a piece of clothing is too young for me, they keep disagreeing. "Age is only an attitude," they say. And it's not true. Just as much as nobody should be told they have to do something because they are a certain age, nobody should be denied their age when they want to claim it.

  32. Jasmine

    Hi Rose, thanks for answering my question. I love blazers. I saw some nice grey items in your polyvore sets. I have been really into grey last couple of years too 🙂

  33. Jasmine


    Thanks for answering my question. Good suggestion, I love blazers. Also found some nice grey pieces in your polyvore sets. I have been very into grey in the last couple of years too 🙂

  34. Jasmine

    Sally, yes. I just resent an email. Thanks for checking.

    Just checked out your Tsubo shoes on their web site. They look much better in your picture.

  35. Jackie

    I'm not so much interested in being age-appropriate as I am in trying to dress well somewhat stylishly for the office.

    I seem to be able to put together decent casual outfits, but can't seem to translate that sense of style into office looks that are appropriate yet interesting.

    I work in an arts center, and wearing slightly more casual and trendy pieces is acceptable. Still, I want to present a more "professional" vibe without resorting to dull suits or slacks-and-basic-blouse combos.

    It doesn't help that many of the more stylish skirts and such seem to be cut extremely short. I'm tall, so many of these barely-acceptable styles look downright obscene. Yet dress slacks are a whole new domain of misery as far as fit and style go.

    Of course, I just used the word "slacks," so I'm probably a lost cause in trying to qualify for stylish over 40.

  36. Lady Cardigan

    I like to do my own thing, but I am conscious that my age (43) affects how I look in some things. I am very thin and have always liked over-sized shirts and sweaters. That waif look was cute on me (or so I thought) when I was younger, but now it often just looks sloppy. So these days I am trying hard to find clothes that fit. And I no longer feel it's OK to keep wearing my jeans after they rip at the knees. That was always fun, but at my age it just doesn't feel cool anymore. I'm still very casual because that's me, but I think about it more now.

  37. Anonymous

    To Anonymous/"M" lookin for a black dress…

    De-lurking on here to try and help (especially since I recently found my current LBD by chance through an anonymous yet super helpful tip on a comments forum [and it was a bad time for me, too—carrying just enough extra weight that none of my clothes look quite right, plus my only black dress had been ruined forever in my mind by a recent string of funerals]).

    Have you tried using search sites like shopstyle {dotcom}?—I discovered that site recentlyish and while it’s flawed (in my opinion, some of the best stuff they feature is just super pricey) it’s a great search engine for looking through some major stores, narrowing by color, size, price range, etc., especially if you know what you’re looking for. Or I often use it to try to find a picture of how a garment hangs on an actual human body when I’m planning on buying from a sale site that doesn’t use models. has been kinda hit or miss for me personally, too, but it’s worth a look—they have a lot of “rules” about what they think looks good on you once they figure out your body shape—though some are helpful and they do allow you an option of looking at everything, regardless of what shapes the garments are recommended for). seems to have a bunch of styles that offer arm coverage if it's super important to you.

    Also, I have no idea what your personal style or price range is, but I think Kiyonna makes some beautiful plus sized dresses… I can’t personally recommend them cause I’ve never worn em, but I love what I see from their pictures… like this beauty, which comes in black:

    Hope some of this helps! Or, even if it doesn’t, that in the end you find something that you feel like your beautiful self in!


  38. Anonymous

    oooOOOooo that ^^^^ is a gorgeous dress! me likey!! thank ya!


  39. budget chic

    Okay, you know I got to weight in on this one. I think folks should just "keep it simple". Many women don't know how to put an outfit together so they over think it by asking themselves is this age-appropriate. If you're a confident individual you will just go for it and if your a person who can truly be honest with yourself, you will know if that outfit was a hit or a miss. You find out what works, what doesn't work based on your body type and then the fun begins. Don't worry about the next woman, if you love it and it makes you feel wonderful. That's the right outfit!

  40. madana

    I completely agree with Rebekah the first commenter. I am finding it extremely difficult being between teen fashion and middle aged fashion… Such a hard one.

  41. Emma at Daily Clothes Fix

    Great post too and timely too as I have just had a birthday. As I wear kids clothes quite a lot (it comes with being short) I do have to be a bit careful about looking age-appropriate.

    But mostly I fall into the category of not giving "a flying rat's ankle" about what others think. Good to have a reminder not to push it too far, though.

  42. Audi

    It's funny, but I found the most difficult time for dressing my age was in my late twenties/early thirties. I didn't feel 'grown-up' enough for more sophisticated styles, but the trendier, younger-looking stuff was simply not me. Now I just wear what I want because I figure I've developed better filters for determining what looks good on me and what doesn't. And if it looks good, then to me it's age-appropriate.

  43. Lanika

    I feel a lot of pressure to be super hot and take advantage of being super hot and young and that the world will end when I turn 20 and it’s ridiculous.
    Just because my age allows me to be accepted by society as attractive (whew! glad I have that approval! means so much to me!), doesn’t mean I have to be all low jeans, high shirts, tits out and short skirts.
    My friends call me Grandma because I’ve been erring on the side of stylistically geriatric since I was 12. Oversized cardigans with extra tissues in the pockets et. al.

  44. Zeebs

    I had a lot of trouble when I was in my mid-twenties. I advise other gals to stick with classic pieces with no logos on them at this age. Forget about logo t-shirts unless they reflect your innermost personality. Go with basics and you can’t go wrong. By 30, I have forgone anything juvenile, but that transition from 22 to 28 can be rough. Anything you see on an under-18 but that would look wrong on 30+ is something to avoid at 25 IMO… took me awhile to catch on to that. Try new stores, and spend more money, it’s worth it. FWIW

  45. Jeannie

    Ah Sally, I love yah. I started looking at style and fashion blogs at the beginning of this year, just because I wanted to answer the question “Can I wear leggings?” at the age of 57. I had started a new job at a local college working with teenagers (for the first time) and between figuring out the relaxed but not too relaxed dress code for staff and realising I needed to be some sort of role model for the students while not dressing in any way like them, I got very confused. Then I bought a beautiful pair of soft grey leggings, and realised I didn’ know how on earth to wear them. I had no tunic type tops or short dresses. But I did wear them completely covered up under a long denim skirt, with boots! Yayyy! I can wear leggings and no-one will ever know!
    Many commentators seemed to think that leggings on 50+ women looked ridiculous or as if they were trying to dress too young. I didn’t accept that, and my search finally brought me too your brilliant blog. You manage to cut through all the judgmental rubbish and talk such good sense, about style and about body-image. Alreadypretty is now my go-to source of completely astute and intelligent advice. Hats off to you (that would be a red hat, with my purple outfit….lol!

  46. Stevie

    I just turned 47 and I dress as I have always dressed – nice tops, jeans and tennis shoes. Well, the style of my jeans have changed from the good ol’ high-waisted, acid wash 80’s style, to more of lower-rise, boot cut, dark denim, but that is it. When I was in school, designer jeans like Sasson, Jordache, Calvin Klein (remember the Brooke Shields commercials?) and Chemin De Fer were in, so was wearing Guess jeans (with the triangle logo torn off). I wore off brands because that is all my parents could afford, so I was the outcast. I didn’t really care at all. When I was in my 20’s, I was a lot thinner than I am now and wore short skirts (not Ally McBeal short). The last time I wore a short skirt, I was 33 and do not feel comfortable going back there now. At work through my 30’s and 40’s, I was very comfortable wearing what I called my “uniform” consisting of a nice short sleeved blouse, tucked into black dress pants with a belt and black flats/loafers. I work at home now and can wear what I believe are my most comfortable clothes – my pj’s. So, I do not go by any style or what is “age-appropriate.” I say wear what you are confident and comfortable in.