Reader Request: What’s “Wrong” With Dressing Casually As an Older Woman?

older women dark wash jeans

left | right

Roxane had this question:

The standard fashion advice for older women (over 40) regarding jeans always seems to be to go for a more formal look (dark wash, lack of trendy decoration, etc. etc.). I understand this if the question is about how to wear jeans in a business-casual outfit or another “dressy” look. 

I’m not talking about throwing on poorly-fitting jeans with a bland, stretched out t-shirt (since most of us interested in fashion aren’t looking for that). And the seriously acid-washed stuff can stay in the 80s, as far as I’m concerned. I’m almost 42, and the whole reason I own jeans is to be casual. I wear them with scuffed up boots or funky shoes, graphics-tees (something else I’m supposedly too old for), or to dress down something sparkly or glam. None of my jeans (all-boot leg or straight) are very dark.

What is it about being “older” that means “not casual” in a particular way? 

This is a fantastic question, and one I’d never really pondered. Why on earth do we all think that women “of a certain age” must suddenly downshift to dark washes for the rest of their days? I’ll get to jeans specifically in a moment, but first the larger question: Why do we expect older women to look dressier than their younger counterparts?

My guess is that it has to do with the loathesome concept of “letting yourself go.” This is snarky, judgmental code for “caring less about the beauty standard and making choices that suit you instead of the patriarchy.” I know that sounds harsh, but seriously, how awful is it that we come down on women for choosing comfort over stylishness as they age? Ever heard someone tsk-tsking about a man who has “let himself go”?

One of the ways we encourage older women to resist “letting themselves go” is to keep their clothes from getting too casual. If you’re dressed smartly, you’re showing the world you still care. If you leave the house in sweatpants, you’ve obviously “given up.” Dark wash jeans are dressier than lighter washes, and considerably dressier than any jeans with whiskering, sanding, or distressing. Ergo people tend to believe and recommend that women over 40 should stick to dark washes. Or, anyway, that’s my educated guess at the social and psychological forces at work.

But the idea that it’s dark washes forever after the big 4-0 is absolute bunk. Peek at Grown and Curvy Woman or Style at a Certain Age to see two stylish women over 40 rocking a variety of jean styles and washes. All style rules are merely guidelines, and age-related style rules are even more guideline-y than the rest, if you ask me. 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.

Related posts:

**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.

Next Post
Previous Post

17 Responses to “Reader Request: What’s “Wrong” With Dressing Casually As an Older Woman?”

  1. mendotawaves

    Yes! work dress codes are being pushed to being less restrictive and as more women retire, and are free of them, there will be an explosion of variety in style. This generation has always expected more freedom in dressing and aren’t going to want to let others restrict them now. There are online sources of any style a woman might desire. At the same time, I think if someone wants to have a less casual style, that will be do-able too. Dressing will be seen more as self expression than as conformity to a false standard set by media and the fashion industry.. Some bemoan the casual dressing seen in this city in fine restaurants, concerts, church. But people can just plain avoid places where others want to tell them what to wear, and go to places where they feel welcomed . Customer bases and organization membership numbers drop.–places learn if they want to attract patronage it’s not acceptable to try to control others.

  2. Linda B

    In less than 6 months, I will turn 59. Last year, I decided that my age didn’t mean I could not wear the distressed jeans that had been completely fascinating me, and though I don’t wear them to work–too casual– I really love this look. It probably is related to my lifelong interest in texture and fibers.

    I am currently wondering whether or not the undone/frayed hem cropped denim look has enough staying power to be worth trying–again, because I love the textural element, not so much because it is au currant. The question is, will it hold my interest, at a time I am more and more drawn to minimalism–which I don’t think is age related, but more about being tired of my lifelong bohemian style. I am loving dark washes, particularly black denim, because it feels more badass, not conservative. Does that make sense?

    I love wearing what pleases me, what matches how I feel internally, for my own reasons. This is getting all the more important with each passing year.

    • poodletail

      Right on. Thanks for your comment, Linda B. Thanks for this post, Sal.

  3. Lisa Wong

    Some of that style advice may be old hat from the days when dispensing style advice first became trendy, too. I remember a time when every woman—regardless of age—was told to wear dark wash, boot cut jeans to look dressier. Then skinny jeans came in, then boyfriend jeans, then white jeans and high rises and distressing…

  4. Suzanne Carillo

    I’m delighted to read this. I just wrote a post about distressed jeans today wondering why they get such a negative rap from the 40+ community.

    What Linda wrote it 100% true. They are textural and add an element of interest.

    Dressing in plain, simple dark washes isn’t for everyone and shouldn’t be forced upon them. I want to look like a clone.

    After all, style is truly in the eye of the beholder.


    • Roxane

      Ugh! Suzanne, that article you linked to in your post is such a great, bad example of this kind of advice I was talking about. Not only the whole “dark wash” thing but the whole “you’ve got to be skinny and fit (aka, young looking)” to wear “young” clothes at an older age. I love your outfits in that post, by the way.

  5. Kerry

    I agree that older women shouldn’t be confined to dark wash jeans, but I have to wonder if part of that comes from the assumption that older women have reached a certain status and that should be reflected in their clothing. We do in tend to expect that women (and men) who are further along in their careers and therefore presumably are more financially comfortable will have higher quality clothing, and perhaps that idea trickles down to casual wear as well, with dark denim being perceived as higher quality.

    • Ginger

      Good point! No one ever mentions status as a reason older women might be expected to dress more formally.
      Even if her bank account doesn’t reflect status, her physical self does. Decking oneself out in items that look like they were in style when she was younger leaves the viewer at odds and creates dissonance.

      • Kerry

        I will turn 40 this year, and while I still like to dress a bit edgy/ funky, I am finding that I want to dress a bit more formally overall these days. I’ve always admired women like Isabella Rosselini for their sophistication and when I was younger I felt like I couldn’t carry off more sophisticated styles that I can now. But certainly to each his own.

    • Kristen

      I think this is a good point. There may be an expectation based around status, whether financial, relational (ie the misguided idea that you’re not dressing to “catch” a significant other), or just mental status. Kerry’s point about age factoring in to feeling like you can carry
      off sophisticated fashions was really interesting to me.

      So maybe people see some
      middle-aged women dressing more formally than they did when they were younger, and then that observation turns into a subconscious expectation for other women to do the same thing.

  6. Kristen

    I somewhat disagree that this idea comes from the idea of not “letting yourself go.” I would agree that that factors into this, but my initial thought was that it relates more to a generational shift towards more and more casual dressing. We are living in a period of time where each generation has become more casual in how it dresses, and a side effect of this is that many people in older generations DO dress more formally than their younger counterparts and are thus assumed to/expected to continue doing so by both the younger generation and their own generation (older generations perhaps having an even different expectation?) There’s an interesting expectation for people PAST a certain age to dress even less formally, however – imagine tracksuits and muumuus and the assumption that “old” people wear those.

    I think there’s also a relation to the idea that trendy clothing is for young people, 20-somethings with some exceptions for celebrities and models/former models. Dark wash jeans are seen as so classic that they aren’t going to break any rules about “trendiness,” while other washes might be in or out of fashion at any given point in time and should be relegated to those who change their wardrobe to keep up with the latest trends (who are assumed to be young.) And maybe there’s an expectation that older women tend to hang onto classic, “investment” pieces of clothing rather than frequently embracing changing trends?

    • Roxane

      That’s such a good point about tracksuits and muumuus being “old” clothes, both in a positive “wear what you want” kind of way and also in a negative “no one will comment because you’re old enough to be invisible” way.

  7. Roxane

    Thanks for the discussion on this, Sally. I’m still intrigued by this question and what the general trend toward recommending “quality” and “classic” clothing for women over 40 says about how we view aging. I’ve really started to notice my own aging over the last few years (now headed into my mid-40s), but I’m still perceived as younger, and “complimented” for it. At the same time, I live in a place and I’m around people where there’s not a lot of policing of older women for trying to look younger. (Quite the opposite in some ways, here in the LA Area.) It leads to lots of interesting reactions to style advice/blogs targeted to my demographic.

  8. Alexandria Blaelock

    I’m from the other side of 40, and I see the debate from the opposite side; that “young” people are choosing to dress more casually. Perhaps it’s a reaction to people like me, or perhaps when they buy $300 yoga pants they feel the pants deserve a seat in a restaurant.

    Perhaps older women have let themselves go, or perhaps they are more noticeable because we expect older women to dress better with all the money we assume they earn as executives. It seems more likely to me that they are just dressing like their daughters.

    For the record, I wear dark jeans, but I preferred them in the 80s acid wash days too.

  9. Andrea

    I thought we stopped listening to the “powers that be” after 40…..

  10. Naomi

    Ooh, such a good topic! I myself am oddly drawn to very “matronly” clothing such as matching drapey- fancy- pajamas- evening- wear, or bulky tweed jackets (neither of which is a great look for me) and I think there’s a couple things going on with expectations or mores around how older women dress:
    1) Gravitas or “earning” the right to wear certain pieces, like heavy, ornate, non-costume jewelry, long silk shantung skirts, or heavily embroidered two piece evening suits. Because of their station/status and obvious age/experience, older women can carry off the regal vibe needed to really wear that type of thing well.

    2) Older women may feel that when they were younger, to feel their most attractive, little “assistance” was needed from their clothing. I myself recall a pair of jeans that had almost no fabric left in the seat that I wore with a pair of mens’ boxers underneath—so cute at 18, would never wear now. As I get older, I like more structure and support from my clothes, and features like darker, smoother washes to create…not an illusion per se, but the best visual look, shall we say. I do have fun jeans in my closet still, though.

    3) Older women tend to know their look and style very well. They might be done experimenting with trendy stuff (or not! no biggie!) and I think retailers expect that as one gets older, one tends to focus less on expressing personality through clothing, and more on projecting a certain persona.

    4) As people in general get older, they tend to make sharper choices financially. If you only have the budget for one pair of jeans, they had better work pretty hard—and a dark, formal wash goes to casual Friday, brunch on Saturday, and a gallery opening Sunday. I myself used to have tons of fun with fast fashion and thrift finds (hello one-piece paint- splatter printed-jumpsuit in nearly see through polyester) and now I’m doing a capsule wardrobe thing and am very particular on my purchases, at age 37.

    Just some possible thoughts!!