Fashion in the thirties.

Last week a friend and I were commiserating about the horrors of clothes shopping, and she said something that surprised me: she confessed to finding fashion for her thirty-something years to be hard. Crazy hard.

The problem, she explained, was twofold. First, it’s a lot harder to find clothes that are comfortable and flattering than it was when she was in her twenties. She’s a mother of twins, and that does certain things to your body. So does having four children, in my own experience. (We laughed about Jennifer Garner and her “baby bump.”)

(I think my friend looks fantastic; she says that’s because she’s careful with her clothing choices.)

The post-twins body dismayed my friend, but didn’t surprise her. The real surprise was this: her sense of personal style, which she thought she’d nailed down years ago, is shifting. A lot. She thought she had it figured out at thirty, but it’s changed.

She asked what I thought, and all I could say was I thought it was just me. 

And not just for low-rise jeans factor: my thirty-something self doesn’t go near those anymore, even though my pairs from ten years ago still technically “fit.”

My sense of style has changed quite a bit in the past few years. A few months back, I stopped to notice just how much my wardrobe has changed in the past year or two: my clothing is now a little crisper, a little more functional, more uniform-y. The color palette has shifted.

My wardrobe is a lot more streamlined than it used to be. It serves my needs quite well. My hypothesis went something like this: as I’ve gotten clearer on what I want and need from life, I’ve gotten clearer on what I want and need from my clothes, and I know what kind of clothes I feel comfortable in (which boils down to pretty much the same thing as what I actually look good in).

I thought it was just me. But as I ask around to my thirty-something friends, their experiences echo my own: my style has changed, they say. So much!

Maybe my relationship with low-rise jeans is over, but I wouldn’t want to go back to my twenties. The thirty-something years aren’t without their problems (this is real life, after all) but I’m so much more comfortable in my skin than I used to be. So many women say they hit their stride in their thirties; I count myself among them.

As it goes with life, so it goes with clothes. By your thirties, you and your wardrobe are finally hitting your stride. You’ve had decades to experiment with what flatters. You know what you need to wear and what you like to wear. You’ve learned who you are, and how to dress accordingly. Sometimes you dress to impress, but mostly, you dress to feel like yourself. A good version of yourself, but yourself all the same.

Or at least that’s the theory. I have a few more years to see where the thirties takes me—and my wardrobe.

How has your style shifted over the years? What’s your experience with thirty-something fashion? As always, tips, tricks, resources, and entertaining stories welcome in comments. 

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  1. First of all, as a reader who has the good fortune to actually get to hang out with you from time to time, I can attest that you look great. Not “great for a mom.” Not “great for a lady in her late 30s.” Just great.

    My wardrobe has always sort of had three components — basic black/navy/gray stuff (especially during my BigLaw years), everyday/ preppy / classic pieces, and a few over-the-top accents. I have to say that turning 40 has liberated me to go a little farther with the third category. I *may* have bought a fake fur vest at Target the other day… 😉

  2. Jill says:

    Yes, yes, yes! I love this line: “as I’ve gotten clearer on what I want and need from life, I’ve gotten clearer on what I want and need from my clothes, and I know what kind of clothes I feel comfortable in”

    And now I am in my “late” 30’s and it’s even more true as I think about my style stepping into my 40’s. I love following trends and dressing stylish (I’m a style blogger after all – but the older I get I can see the trends falling by the wayside as what I like, what feels good on me, and what is easy takes precedence. It by no means I have “let myself go” – but it is quite freeing!

  3. Sara K says:

    I agree wholeheartedly! I am in my mid-30’s, and I can definitely see the changes in my fashion choices. Now I am much more likely to go with classic than trendy. I like clothes that slim and hide flaws but that are comfortable, neat and tidy. I know the colors that look best on me, and I avoid colors that I just can’t wear. Goodbye yellow 🙁

    My biggest fashion issues right now are two-fold: 1. dealing with weight fluctuation can mean I have a closet full of “just a bit too tight” clothes and 2. There’s a difference between knowing the style I like and finding it in a store in my size, color and price I want.

    Overall I feel that I’ve hit my stride in my 30’s and am definitely more comfortable in my own skin than I was in my 20’s.

  4. Rebecca says:

    In my 20s I had no sense of fashion-it was a combination of “I don’t care” and “I really have no idea how to pick out clothes”. But my brothers picked out some really fashionable ladies and I don’t want to be the frumpy older sister (I’m the only one with kids, that may explain everything right there) so I’m paying attention now. I like mid-rise boot cut jeans, dark denim, and flats. I like v-necks only, somewhat form fitting. And lots of steampunk jewelry. I think if I add a blazer into the mix I can declare victory and go back to ignoring the fashion world lol.

  5. Susan Skinner says:

    I am 57. It is fun to see things that I wore earlier come back to life. It is a bit of a challenge sometimes to pick up the trend and adapt it once again. I am much more aware of comfort and function than before and feel blessed to work from home where my own style is the workplace style.

  6. Shannon says:

    I had a good run there for a while. Once my kids hit elementary school, I put more energy into my outfits, started wearing fun jewelry… But now (I’m 41) I’m back in a yucky place where I don’t make the effort, and when I want to pull it together, I can find clothes that fit my body–which fluctuates with whether or not I’ve been eating too many sweets and drinking too much soda. Blah!

  7. Linda Stoll says:

    By 60, you really hit your stride! Comfort’s a big one. Lots of black and gray … and tops that bring color. Fleecy vests and boots.

    Scarves, too.

    Until mid-spring. And then it’s all about the flip-flops …

  8. Ashley says:

    The topic of 30-something fashion is so … fraught, maybe? Even when I was younger, my body type made it really hard to do the trends that other people pulled off effortlessly. Having kids has sort of exaggerated that body type, and I find that I’m most comfortable and look best in classic styles. I thought I was hitting my stride in dressing myself! But after some recent feedback from my husband and my sisters, I’m wondering if my style is coming across as more OLD than classic. They keep gently pushing me to take more risks and I’m honestly not sure how to take their feedback. They seem to think I lack confidence in the wardrobe/beauty department. Here I thought I was doing a good job expressing myself, so the comments (though well-intended) stung a bit.

  9. Margie says:

    I’m 35 and I agree. My style is changing but for the better. I don’t feel the need to dress for others anymore and realize how little they care. I’m heading towards the uniform of quality pieces that fit me well and a much smaller wardrobe. My usual day is stay at home who bikes her kids to and from school.

    I tend towards good jeans, high quality boots and striped tops. Could be button down, tunic style, sailor style, but pretty much all striped shirts. I’ve got ankle boots, knee boots, rain boots, tough boots and dress boots, but pretty much all boots. For jeans, I swear by the Nordstrom fitters who really tend to know which styles work on what body types, then when I wear out the rear by the pockets, I replace them on eBay. It’s obvious when you look in my closet how repetitive it is, but even my good friends never notice or comment.

    Do you ever read the Vivienne Files? She has been running a series on building a wardrobe from scratch, based on the first sixteen pieces that would give you a solid wardrobe of options. I find that some of her selections veer older (more early fifties?) but that I could think through that process in my own closet and see where I had too much and where I had holes.

    • Anne says:

      I’m not familiar with the Vivienne files. Thanks for the recommendation!

      I wish we had a Nordstrom here. I always appreciate someone telling me “that looks great!” or “PASS.” 🙂

  10. Brit says:

    I absolutely agree with this. I just finally got into my mid-twenties and I feel like I’ve finally gotten a little more of a cohesive style than I had before. I am not like this by nature, I kind of had to force it in order to get a wardrobe where pieces actually work together. I was really into theater and reading and general daydreaming so I always approached clothing as costume for who I wanted to be that day (Victorian governess, ’70s fashionplate, ’30s era street urchin). Which is why I ultimately ended up with a bunch of pieces that didn’t really go together. As I’ve gotten older I’ve definitely gotten better at editing.

  11. I feel like I’ve gotten more realistic about what I’ll actually wear. In the past, I bought things (likely on sale) that “might be cute for a (fill in any random event)” but that I wore rarely, if at all. A few years I started to identify the kinds of pieces I would reach for over and over again and am more willing to pay for such items. That being said, I’m not sure if I have a signature look or a great sense of style. Day to day, I prefer some version of black workout pants and top. If I am wearing jeans, my kids assume I have a meeting to go to. I’d like to step up my game, day to day, but I can’t resist the allure of comfort!

  12. I’ve had the exact same thing happen to me, but I assumed it was because I spent three years out of my formative thirties in India. There I wore bright, beautiful tunics, slim jeans, scarves, and always a little sparkle. This “uniform” downplayed flaws, played up my femininity, and made me feel like nothing was accidentally showing. I came back to the States and, consciously or unconsciously, looked for clothes that would do the same thing. I’ve found them, I think. It’s taken me a while (I’m 38!) but I think I know what works for me now. Here’s to finishing the thirties strong–and heading into the 40’s like a boss. 🙂

  13. Katia says:

    I don’t usually keep my age at the forefront of my mind when making decisions regarding clothing. However, I would agree that my style has become more streamlined over the years. I know what I like, I am comfortable with my body, and I enjoy practical outfits with funky details, whether these are my form-fitting yoga clothes or work outfits. These days, I rarely shop for clothes and when I do, I am not afraid to spend a bit more money on a few quality pieces that I know I will continue to enjoy for several years. My wardrobe is smaller but I know exactly what is in it and I like each piece. Unlike in my 20s, I no longer have a closet full of clothes and claim that I have nothing to wear.

  14. Bethany V. says:

    I think my perspective on clothing has changed a lot in the last few years. I’ll be 33 in less than a month. I have two children, the youngest is only five months. Prior to this past pregnancy I put a lot of time and thought into my wardrobe for the first time. I wanted to like my clothes. I started buying cardigans and scarves. Wearing for fun accessories and shoes. Yes, shoes.
    But I also started becoming more aware of where my clothes come from and how they are manufactured. Yes, I still buy conventional items, but I try to do it more deliberately and make more ethical choices when I can. Sometimes this means buying second hand or not at all.
    I think one of the most frustrating things in my life right now is that I have a closet full of clothes that I love and looked good on me, until this past pregnancy and now I’m twenty pounds heavier. I’m hoping I can get some of this weight off and get back to wearing things I love and that (I hope) still suit me.

  15. ailikate says:

    I think body image and comfort with that image has been a big part of this for me. In my teens I just wanted to hide, in my twenties I wanted to be seen but was afraid. Now I’m not trying to hide or be noticed, I’m just being. I’ve realized that part of comfort, for me, is looking at least presentable. Also, I’ve embraced the fact that I just feel better in skirts and dresses, more comfortable, warmer in the winter and cooler in the summer. Finally, I’ve stopped holding onto clothes that are “almost” right, or that I feel like I “should” like, even if it means feeling like I’ve wasted money. Less of that, though, now that I know better what I will actually wear.

    • Anne says:

      “Now I’m not trying to hide or be noticed, I’m just being.”

      Love this.

      I also relate too well to what you said about holding on to clothes that are “almost” right.

  16. Jill Foley says:

    I’m in my forties and am feeling like I’m just finding my style. I stumbled upon “dressing your truth” last year and it’s been so helpful to me – matching my natural energy level and personality with how I present myself with clothing choices.

  17. Jeannie says:

    I don’t have anything too profound to contribute, but I remember saying a few years ago that I would NEVER adopt the “skinny” trend. I enjoyed my boot-cut pants and saw no reason to change; also, I was nearing 50 and thought skinnies were a young woman’s thing. However, a few of my pants that I’d had for years were starting to feel a little snug (I’m 50+ so probably menopause is playing a role). So I decided to buy a few new pairs of pants this past year; I took the plunge and tried some skinnies. I love them. They are so comfortable and flattering. So when it comes to fashion, I’ve learned never to say never.

  18. Ashley says:

    For me I think hitting thirty marked a milestone where I very consciously thought about dressing “as an adult.” Fortunately for me it happened to align with a major job change where I went from teaching at a preppy all girls school to a faculty position at a public university. I took what I learned about classic pieces from the older, well-dressed women at the academy and sought several new pieces for my wardrobe, specifically well-tailored slacks (thank you Limited card for getting me free hemming!) and well-priced blazers from the outlet mall. I even cut my hair in a shorter “big girl” style. All of this helped me to dress with confidence in my new work environment, while also paying attention to trendy and stylish colors and pieces (particularly scarves and dresses). I found the whole process very fun as well (who doesn’t like an excuse to shop for a bunch of clothing?). I hope as I go through my thirties to settle into less pieces in my closet with more interchangability among them. Closet space is at a premium in my house! Dream: a walk-in closet that isn’t taken over by my husband’s million hanging shirts.

  19. Janaet says:

    I’m a lady of a certain age and I always remember that you don’t want to dress mutton as lamb. So even though there are some styles and colors I like, they just aren’t appropriate. I have a simple color palate, black, grey and blue with a dash of pink thrown in occasionally. Still wear jeans, but not low cut.

  20. Kayris says:

    I’m 37. And while I have a definite idea of what looks I like, finding age appropriate clothes is hard. Shorts, for example. The choices seem to be booty shorts or old lady shorts. When I found shorts (at Old Navy, a store that usually sells short shorts and nothing else) with a slightly longer inseam, I bought them in every color they had. Target is hard too. The clothing department goes from juniors, with clothes with witty sayings and cartoon characters on them, straight to matronly and boring old lady clothes.

    • Margie says:

      J Crew shorts come in 3″, 4″, 5″ and some in 6″ inseams. I find 5″ to be perfect for my mom of two littles life style. Short enough that I don’t feel matronly and long enough that I can squat and bend and lean over as needed without feeling like things are going to hang out.

  21. Libby says:

    I’m in my mid-twenties, and had the realization a year or two ago that this is the youngest, prettiest, and skinniest I’ll ever be, and if I want to try a look out, now’s the time to do that. So I stopped worrying about whether or not I could “pull off” a look and just started wearing stuff I liked. This may have involved buying a pair of high-rise, velvet, black houndstooth print pants at a thrift store for $9. I adore them and think they make me look awesome. I also adore my colored skinny jeans, which I know were trendy years ago, but since I wasn’t bold enough to wear them then, I get the benefit of finding multiple pairs for under $10 at thrift stores! I like to view it as collecting my own trends: each season I get to sample whatever fashion decides is in, buy what I like and what looks good on me, and together all of those make my personal style that’s trend-less.

  22. I’m still two years from my thirties and, being single, have approached it with a mix of dread and excitement. Dread because I thought I’d be married by now. Excitement because I hear everyone say that you get more comfortable with who you are in your 30s. I could use some of that. I’m tired of the angsty 20s.
    But I DO feel my personal style settling in better these days. And I finally like my style pretty well, which is new for me. So if that’s a result of getting closer to 30 I’m all for it!

  23. Heather Braun says:

    Great post and good comments. I am 52, and it is interesting to note that my style now is eerily similar to my high school / college days. With the exception that my hair is now silver and as Janaet said, I’m not dressing mutton as lamb.
    Be willing to flex your style, but stay true to who you are.

    • Anne says:

      “Be willing to flex your style, but stay true to who you are.”

      Well put. And it’s interesting to hear that things have come full circle for you.

  24. yettie says:

    I’m in my late 30s and got the post-twins body too. My fashion has probably come full circle for me I noticed. In my early twenties, I noticed my wardrobe was black, white and blue. I revolted and went on a color binge for years which I thoroughly enjoyed. Now, I’m moving back into a neutral zone with my color scheme and I’m quite happy about it. Difference is now I can afford better pieces and definitely know what looks good on me and what doesn’t

  25. Brenda says:

    I’m 52, and I knit. I was taking a class on sweater knitting and the teacher talked about people fitting into different categories for clothing and fabrics, and I thought this would be the same-old classic vs trendy. But then she said people were either “stiff” vs “draped” and “shiny” vs “matte.” I was a bit floored. I realized almost immediately that I am a draped/matte person in terms of fabrics looking flattering and being comfortable on me, and therefore, I should probably stop buying polished-cotton, buttoned shirts in the vain hope I would find something I like. It was the most informative styling advice I’ve ever gotten. And, I’ve also stopped trying to get my stiff/shiny husband to wear lambswool sweaters, and I leave him to his buttoned shirts that he likes starched!

  26. Kimberly says:

    I recently turned 50 and I am finally really comfortable with being comfortable with myself, my body, my style, and wearing comfortable clothes. Several years ago I started using a capsule wardrobe. It was a great process of editing and curating. Now I only purchase items I love, feel comfortable in, and work well with other pieces I already own. I care less about looking trendy/fashionable and go for classic pieces that work well for my body style (which when you are going though menopause can be interesting…laughs). I also try and find items that will last a long time, I’ll pay more for quality, because for me it is about the quality and not the quantity.

  27. Katie says:

    I’m 29 (will be 30 this summer). And maybe I’ll get to this magical comfortable-in-my-skin moment sometime in the next decade, but I suppose it makes sense that I currently feel completely deconstructed. You have to break it down to build it back up, I guess.

    I’m completely lost. I have no idea what looks good on me anymore–and nothing feels good. I’m fat now, with a body that can’t be blamed entirely on the babies, and nothing that used to work for me works any longer, yet I haven’t figured out what will work. And after three years of working from home, I’m now back at the office part-time–so all the SAHM stuff I had figured out is back out the window. It’s just miserable. Nothing I own fits well even if I can squish myself into it. New larger pieces I buy also don’t fit right, or feel right. And I have zero money for clothes, because having to go into the office means a paycut with daycare costs, and we were paycheck-to-paycheck before.

    So I’m looking forward to this 30s revelation, but at least my clothing situation can’t get any worse!

    • Bonnie says:

      Oh, girl, I feel for you! Parts of your story rang so true for me. I’m way older than you, never got to do the SAHM thing, but have put on weight it’s terribly hard to lose, and can totally relate to the paycheck to paycheck life (for YEARS). A few years ago my head was pretty much where yours is now, and I spent a whole winter wearing either black pants or a black skirt with a sweater or shirt. Now that I’ve discovered scarves, I would add a scarf. I wore this to church as well. No one ever said a thing about my “uniform”–I seriously doubt they even noticed. Get a black cardigan and maybe a gray one, and you’re set. I also wore knee boots almost exclusively with the skirt. The skirt was a “slinky” type that never wrinkles. The pants were from WalMart. Many people now love the ponte pants–I haven’t tried those. If you have one pair of jeans that fit you well, you’re good to go after hours and on weekends.

      Not knowing your office dress code and your personal style, I don’t know whether this helps at all. Just know you really don’t need many pieces, it doesn’t have to be expensive, and the more uncomfortable you are with yourself, the more it will show to others. Find a good resale/consignment shop, don’t write off thrift stores, and ebay is a good source. Go to stores and try on things, looking for things you like and that fit you. That makes eBay shopping way less risky. Sale and clearance racks are your friend. Also, Google capsule wardrobe and Project 333. Lots of great ideas out there, especially if you’re a big Pinterest person (I’m not). Good luck on this new phase of life.

      • Katie says:

        Thanks, Bonnie! I have a couple of dresses that I like okay still, but most of my leggings don’t fit well (my kingdom for a pair of leggings where the top doesn’t roll down!). I can kind of piece together a few ok work outfits, and since it’s so cold in the office I’m pretty much huddling under a cardigan and scarf anyway. 😀 But ugh, I canNOT find a pair of jeans that fits well! It’s terrible.

        I’ve never had good luck at thrift shops, and with two toddlers the concept is less than appealing, ha!

    • Anne says:

      I know people say “it’s just clothes,” but wearing the right clothes—-or the wrong ones–can be completely life-changing.

      Here’s hoping that “completely deconstructed” is a good place to start. There’s a reason “building from the ground up” is a tried-and-true method, right? I hope so. 🙂

      (When my own wardrobe was in post-baby shambles a good friend who was naturally gifted at the whole wardrobe thing told me to just find ONE THING that I felt good in and go from there. I hope you find it soon!)

      • Katie says:

        That’s my hope! I definitely struggle with knowing what looks good on me, too, which is frustrating since I had it figured out before babies–but none of it looks good anymore. Mostly, I just would like some shirts that are long enough for me not to end up with my belly sticking out the bottom, and some pants/leggings/jeans that STAY UP. :-/

    • Ellen says:

      I am right here with you. I did not expect how a baby would so throw me for a loop in what I previously considered a frivolous area. My own body is so strange to me. Yet I have the same feeling of being broken apart so I can rebuild, which is after all a positive thing. And thred up. Love that site.

  28. Meghan says:

    I had a big career change in my late 20s — not so much the content (librarian to freelancing in publishing) but the location — and also two children at 29 and 31. So my wardrobe needs and body both changed as I hit my 30s. Now I scramble to pull together a professional outfit for the 1-2 conferences I attend each year! I do enjoy dressing like a “grownup” though, and prefer not to spend all day in pajamas or yoga pants even though my clients never see me, but that’s just personal preference and how I work best. Anyway, my style went from being tailored tweeds and suits to more relaxed jeans and fun tops, or funky dresses, and all high quality since I can afford it. Fewer pieces, but they last longer. And luckily a couple of those library-days outfits still fit well enough to get me through a 3-day conference 🙂

  29. Karrie says:

    Two words. Jag jeans. I found mine at Dillard’s. Higher waisted with an elastic band up top. But they look like regular jeans, not maternity. Very flattering and super comfortable. They are what I throw on when my yoga pants won’t cut it.

  30. Amy says:

    My latest favorite clothing item…the Ann Taylor perfect shirt. It gives that “crispy” look, but it is surprisingly comfortable. Cute untucked with jeans or dressed up for work. I have a couple of white ones, a blue one, and I am wanting to collect more colors. Also, Ann Taylor is always having great sales!

  31. Annette says:

    I was just thinking about this. I have pretty much gone “uniform.” In winter, I wear a cute top, a cardigan, good jeans and boots (ankle or knee). In the summer it’s a cute top, a skirt or shorts, sandals or flats.
    I’m comfortable, feel cute and the outfit is appropriate for my age (52) and my lifestyle.

  32. Angela says:

    I turned 31 last month so I’ve yet to really see my style change. I hope it would because I hope to enter new seasons in life. I’m single and one day hope to marry and have kids. Sometime in this decade of my life, I pray! And I think my style would change then. It hasn’t really made a lot of changes these past years. The biggest change is I’ve become more comfortable and loving of my God-given physical body, flaws and all, and my style has reflected that. Still modest, but I no longer mind showing my knees (one has a huge keloid scar) or flabbyish arms. I no longer wear big shirts over my bathing suits. I’m more bold with my hairstyle too. It was a journey to stop hiding behind clothes and the name of modesty.

  33. Asha says:

    This post, as well as some other recent ones where you mention hitting your stride in your thirties, and the many wonderful comments, have made me very much look forward to my thirtieth birthday this year! Thank you (and all the commenters) for the perspective!

  34. TiFFANIE says:

    I’m actually in my 40s, but my wardrobe has not really changed that much honestly. I’ve always been somewhat fun and free spirited/rebellious (think boho) with what I choose to wear. I like being on trend, fun and somewhat edgy with my style. I don’t see that ever changing.

  35. Anna says:

    My wardrobe is more streamlined. This is partly due to simplicity, but partly due to knowing what looks good on me now. I used to buy a lot of things that looked cute, but I didn’t like the way they looked or felt. It took me awhile to be more realistic about it.

  36. Coffee Sipper says:

    Hmm, interesting. I thought it had more to do with having read Lessons from Madame Chic, and Jennifer L Scott’s other books, personally. But maybe age does have something to do with it too. I find that I like the idea of the capsule wardrobe, in part because it cuts down on laundry. I also find that though I’ve always been inclined to shop frugally, I’m more likely than I used to be to pick out a few nicer items less frequently and pay a little more (shopping clearance or sales so I’m not paying full price, of course) but the quality is better and hopefully the clothes last a little longer.

    What are your thoughts on this, Anne? Have you read Scott’s books? What do you think of them?

  37. Hehe, when I first clicked through, I was all “I wonder what Anne is going to be sharing on fashion in the 1930s!”

    I completely agree on fashion changing in the thirties. Even things that technically fit from the pre-kid days just aren’t my style. I wrote about the changes in fit preference recently actually. “Why so clingy, shirt?” (I never did get the suspenders though.)

    I think the changes are a combination of knowing more of what I like and then being OK with wearing it. I don’t think anyone notices if I wear gray all the time, and even if they do, I don’t really care. Overall, very freeing.

  38. Lynn Wegmann says:

    At age 56, I’ve come into my own, style-wise. I’ve learned that classic styles suit me. Whenever I try to get something trendy, it ends up at the back of my closet, or in the Good Will bag. If I want something unique, I add jewelry and/or some interesting shoes. I also have a number of pieces that I mix or match. I love Cabi clothes, and these are usually my wardrobe staples.

  39. Cerise says:

    When I turned forty this year, I joked that now I’d have to start wearing turbans and capes and red lipstick and giant cocktail rings and calling everyone “Darling.” Honestly though, I have found my sense of style shifting this year. In my twenties, I had sort of a crisp soft butch look during the work week, with plenty of pants and button-up shirts, with a more rock ‘n’ roll vibe on the weekend. In my thirties, now a mother, I found that pencil skirts and wiggle dresses were more flattering to my new curvier frame, so I cultivated a vintage look. Hats and heels everywhere. I really sought out those pieces for a long time, and I’m disappointed to find they’re not doing it for me anymore. I’m starting to be drawn more to edgy, avant garde styles. Less Dita Von Teese, more Tilda Swinton. Hell, I’m even wondering if I could pull off Tilda’s hairstyle, even though I’ve been pursuing Old Hollywood waves for ages. (I’m starting to get a few grays, all in one place at my right temple, and I’m reeeealy hoping it develops into a big white streak.) I’ve been drawn to dramatic jewel tones all my life though, so perhaps some things never change.

  40. Becca says:

    This was such an interesting read. I was too afraid to dress how I wanted in my twenties, thinking people would sneer at me for being too fat, too square, whatever. Now I’m in my 30s, with the help of amazing bloggers like Zoe de Pass and Leandra Medine, I’m actually starting to enjoy dressing again. So what if I weight 220lbs? So what if my breasts are not in the exact same spot they were in pre-kids? It’s not my job to be either sexy or invisible – I just need to look clean and tidy, so beyond that I’m having fun with clothing – colours, textures, shapes and personality. At 34 I have become that crazy old lady who wears purple.

  41. Ray says:

    I turned thirty this year and I found exactly this when I started to consider refreshing my work wardrobe. Things that suited me in my twenties, no longer seem to, even colours, like black, no longer seem quite right. Like you I thought it would get easier as I became more sure of myself! I’m still working it out but I intend to have fun whilst doing so.

  42. Laurel says:

    I am almost 60. I’m finding it a challenge to look contemporary and comfortable. I don’t want to look like my 20+ daughters and co-workers … I’ve been downsizing my closet to only have clothes that I feel good in and that look good on my tall frame. Your posts on the topic of clothing have encouraged me. Thanks!!

  43. Deborah says:

    I’ve been pregnant or nursing for most of my thirties. So I don’t think that this holds true for me. But I bet it will for my forties!

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