Irina - you're right. The pieces I'd like to try are often just out of my price range. I have a few pieces to start with, but it will be a slow process. I have a limit to how much time, energy and money I can and want to put into the pursuit of style, and that's also a limiting factor.

What Vildy said makes so much sense to me. Agree with her. Also nodding with Ummlila. You've never appeared kooky or overly eclectic. Never. I understand the wish to avoid that look. I, too, wish to avoid it. But I also need a certain amount of dynamism in my outfits to feel like myself. So it's tricky.

I think you look great: Your hair looks polished and chic and the all-black look is sharp--those ankle strap espadrilles bring the glamour!

I hear what you are saying and appreciate your interest in self-reflection and trying to evolve your style in a mindful way, though I agree with everyone else that your outfits always look good! I don't have much to add beyond the wisdom already shared...It's a balancing act, it seems to me, between more understated/minimal and more colorful/hectic. I get bored (and don't feel like myself) if I go too minimal, ditto if I go too hectic. Maybe it's similar for you, but you are wanting to lean more heavily on the understated chic end of the continuum?

My two cents on that Instagrammer: Her big, curly, slightly wild hair is doing some of the work because it's in contrast to her minimalist, luxe outfits--the juxtaposition is what's especially interesting and eye-catching, IMHO. So for each of us, it's about figuring out that pleasing relationship between our clothes and the rest of us, if you know what I mean?

LJP, I have never followed you closely, but from what I have seen, you frequently say that you cycle through things rather quickly. If some of those things that seem just above your budget turned out to be “forever” pieces….you know the math.

Also, I’m thinking about your title here. I don’t think any of us want to be caricatures of anything, but I do think growing up and growing older are all about becoming more and more ourselves. After reading your post, the outfit was jarring to me, because for me, the classic edgy look is all about pretending. I am emphatically *not* saying that you are pretending, but that I most certainly would be if I were to run around in that, just as you probably would in some of my bright colors, ditzy florals, and short skirts. I do think your bracelet is both cool and something I could wear, in juxtaposition to the rest of an outfit, but the rest would be uncomfortable for me. (Don’t know if you were around then or not, but there was a little thing for a while of a couple people insisting there are no rules in my style, before some other folks helpfully pointed out that juxtaposition and intentionally having that one piece that makes you look—uncomfortably—is in fact a rule, and I’m not just insane or a trash heap). So cool to see people coming home and being comfortable in who we really are. Rock on.

Your outfit looks great but I think you always do. It's funny how the way we see ourselves can be so different from how others see us. I don't feel like you ever looked caricature-ish

I know for myself, I look at someone like that Instagrammer above and love her style but I put on a button down and v-neck sweater and it just doesn't have the drama on me that it does on her. It seems good in my head but doesn't translate. I think I am struggling because my age makes some things that I have always liked feel inappropriate now. I want to look stylish but not trendy and I want to look good but not like I am trying too hard. Maybe you are feeling some of that too.

SF - I’m sorry , I don’t understand your comments .

You & I are different & I think that’s great—makes the world more interesting & fun.

If you meant the first part, I’m saying that if you stretch your budget to get the things you said you’d really like and then keep wearing them, the cost per wear could eventually be lower than the cycles you say you go through now.

Robin- you’re right . Too basic, and an outfit looks plain and uninteresting unless you’ve got something else going on - like really great jewellery or hair or whatever . It’s a real balancing act I agree . I’ll never stray into classic / basic territory ( button up shirts , v neck sweaters , plain trousers etc) as it’s so not my comfort zone and that’s where the artier / edgier versions will fit in .

SF - yes , I’m well aware of the economies of my wardrobe . It was the second half of your reply I don’t follow .

I hope it made more sense in the condensed version.

Yo, Lisa, I started to think about the caricature thing (regarding myself) maybe even before I read your post or maybe about the same time. I recently bought the black moto vest because my old one has started to peel, and then I showed everyone the cream moto jacket from NAS. Both have extreme '80s shoulders which I rather like, but they're darn EXTREME. And then I bought (still have to make a final decision) the pearled up Chelsea boots that were cheap as chips ($28), not to mention the Kors boots which are gaudier than they look in the stock photo. AllSaints skirt is not exactly classic.

I've never aspired to classy, glam, or luxe which is probably a good thing, right? Fun and silly work better for me. But these last couple years have made me very conscious of anti-Asian violence, particularly against older Asian women. So a part of me wants to look very fierce, and who cares if the look is too young if it keeps me safer. But yeah, I would probably be better off if I took a self-defense class since my extraordinarily strong and sculpted calves (from hill climbing) won't do a thing to protect me.

You always look a cut above to me so I continue to be baffled by your dissatisfaction but of course I will not dispute your feelings. Maybe stop following bloggers? I am oblivious which for me is bliss, lol.

You write so well! And you look great. And yes it's relatable.

One thing about following others "looks" is that my brain fills in a narrative about HOW THEY FEEL. Sorry to scream, just for emphasis :). It's the photo...the light, the background, one imagines so many things about their satisfaction level...their lives. That I think probably isn't even true! One can come up feeling short. (studies done on girls and social media and body and inadequacy issues). What would happen if you went on a "diet" of less outward influences and more paying attention to what you are self directed to wear? Just curious, not trying to tell you what to do.

I enjoyed reading you...it's a journey for sure. Be kind to yourself!

Oh dear . I didn’t intend for this to go in this direction. I regret expressing dissatisfaction and feeling unduly influenced . It’s less dissatisfaction than it is interest and excitement for an update :). I actually don’t think I look kooky and like a caricature - yet. That’s not the concern .

duplicate comment

I love your outfit, and if that is the direction you would like to take your style it totally works on you. I look forward to seeing more.

Very well said, Lisa-and it all really resonates with me, including doing the same old mistakes when purchasing some new things without thinking and measuring 1000x on all aspects of our new adition! But it is an unbelievable hard work as we have to break up with old belove habits/looks ingrained in our former minds + Brooklyn said so well -the urge to adding new it's mostly because creative (like some of us:-)) get bored easily.

And, Jonesy said my two cents on that Instagrammer, and the essence of the AUTHENTICITY too: "Her big, curly, slightly wild hair is doing some of the work because it's in contrast to her minimalist, luxe outfits--the juxtaposition is what's especially interesting and eye-catching, IMHO. So for each of us, it's about figuring out that pleasing relationship between our clothes and the rest of us.."

Looking at my comment it was all a copy and past, not very original---but felt like nothing to add is eve more at the moment!:-).

Anyway, I'm so happy you came back, and will follow your way of achieving your desired looks-as you are a great inspiration for me+ am sure you'll arrive there sooner than you think -just don't be afraid to try and fail sometimes-that's only an inner feeling. With this kind of awareness and power of thinking You could never do a fail that big observing from outside!
Loved this outfit-and especially the piece of mind it brought to you!I am too consciously collecting my outfits which give me simillar feelings, for a while....In fact they many are revivals of the some much older ones...:-)

I haven't had a chance to read all of the comments yet--just wanted to say that the whole look is fab. If luxe is what you're reaching for, you got it. Fit, little details like the wedge and ankle strap and your beautiful skin/hair all look so good! (BTW, I just finished Billy Summers. My second SK and I liked it.)

I do have a notion to do a David Bowie at some point - how he went from glitter and spandex to suits. I’m already tired of my sofa - which is very heavy to move for vacuuming. I’m pretty sure I will be like my mum and only sit in one chair. No fuss! No digging through the closet!

How much do you like your couch, Rachylou? As much as James Harden likes his couch?

How does he FIND his couch?! Lol

I've been thinking about this title ever since you posted it--becoming a caricature of one's self.

I wonder if that's what happens when we cling too hard and fast to what we think are our rules, rather than when we allow for incremental growth. It's a comfort thing. When my son was in middle school, he wore the same blue puffer vest every day like a cartoon character. He was scared no one would recognize him if he wore something different. I feel the same pull when I think about the people who wear one dress for a year or about Steve Jobs and his turtleneck and jeans. the idea of knowing your style identity and sticking to it for a lifetime is COMPELLING, but it's also unrealistic for most of us, so we experiment and grow and sometimes fall back into old habits and sometimes find a whole new direction that magically "fits,"

I'm just rambling here, but what you write resonates. We're not who were ten years ago, but we also are still who we always were so in fashion and life we have to find the path that marries those two truths. It's a journey.

Also, I like your outfit.

Oooh Jenn that is so well said ... I've totally done that ... Felt the pull to something new and resisted because "I don't wear that".

And love that you are excited about what's ahead style-wise Lisa ... That's a great place to be.

I’m late reading this, and doubt I have much of value to add other than to say I think your thoughts are compelling, and heartfelt. I like the direction you are taking and find the pictures you posted very flattering. I personally do not enjoy wearing black or all black outfits, yet there is a very classic and elegant magic it brings to outfits which is undeniable. For some reason, the word balance comes to mind when I look at your pictures. When wearing an all neutral/black outfit, the shapes, textures and lines become more relevant, and you have developed mastery of these elements.

You look great! I can definitely relate to wanting simplicity, though probably a good idea to keep some of the flashier pieces for when and if the mood strikes.

I think many of the Instagrammers just wear all the impractical, OTT stuff for the pics TBH. It's just like fashion magazines or runway shows, just inspiration, not real life.

When I refer to instagrammers, I don't mean influencers. I'm talking about women in the fashion industry - usually editors and stylists. Big difference in my mind.

Thank you all for the interesting and thought-provoking comments. I love this kind of conversation

I can relate somewhat as I always experience some conflicts and perhaps “ mistakes “ when I try some new things especially if I did so after kind of lemming action prompted by ads, sales, wantsies. Some of these were also good experiments.
I relate to the goal of subtle luxe elements and felt I achieved more of that and more of my style in my professional wardrobe. It’s been much harder in focusing on more casual, durable, washable fabrics- and hot summer makes that harder because a lot of tech and synthetic fabrics, which at higher end can often be rendered in sleek or “ luxe” looking garments that are washable , with clever details, are just too hot.
Still, I’m trying to pay more attention to which items and silhouettes feel the most “ me” regardless of trends and think how I might bite the bullet to pare down, cull out some of the experimental or impulse chaff.

LJP I love these types of conversations too - Jenn's final sentence really captures it for me "We're not who were ten years ago, but we also are still who we always were so in fashion and life we have to find the path that marries those two truths. It's a journey." Thank you for this thread and sharing your journey with us.

What you say makes sense. I dress pretty bland and frumpy most of the time, nothing that would stand out. When I feel like wearing crazy stuff I wear it someplace like the mall or driving or out hiking in the middle of nowhere. There are always places where you do what you want. The stuff in your pictures looks fine you don't look like a crazy looking catalog model or celebrity, you look nice but normal and very appropriate. Also it's good to remember we only get so much time so we should live a little, I always try to do that.