Angie, for sure - no one is a paragon of self-confidence in every area - but you sure are one in fashion

Liz, so smart - I wonder if my style words would change if I ran them through the frenemy filter?

Sara, I live in the 'bump into' capital of the universe ... literally can't sit on the porch without someone saying, who were you sitting out there with the other evening? It makes for perhaps a little more self-consciousness than city living does!

Suz (and Janet and Lisa) - love your confident attitudes!

notsaf, I'm quickly learning how many problems regular exercise solves!

Lisa, I see your point - yes, 100% dressing for the intended audience makes perfect sense. I guess I'm thinking more about the surprise audience. One mundane example I can think of was running into a mom that I knew through one my kids' programs, but not well. She was nice enough but vaguely intimidating and from a specific group of woman who were all quite wealthy and successful. I was wearing a nice, day-appropriate outfit but as soon as I saw her, it may as well have turned into a peacock costume. What started as a simple outfit with a pop of colour in the top (bold berry-ish pink, a favourite) with a statement necklace, turned into sloppy and garish in my mind - whereas I don't think I'd have felt that way in a more minimal, neutral outfit. I thought it was my style when I put it on and would still swear it is - but it sure didn't feel right under the gaze of this particular woman. To this day, if I feel I might run into this group, I wear a black sweater and understated jewellery and accessories. (sounds so sad as I write that *sigh*)

So - was it my style and I buckle to easily under pressure? Or does this example help me hone in closer to what's truly my style vs. what I just find aesthetically please to look at and assemble? Does that make more sense in terms of the dilemma?

Heh, I’m laughing a little at all the “bump into” comments. I’m from a place we call “Smalltimore.” It’s pretty much guaranteed I’ll bump into an ex or someone I would like to leave with a good impression, no matter where I go. I guess some days I just care more than others.

I really relate to what Jenn said. I often plan my outfits on the basis of other outfits I loved in similar situations. The goal is always to feel my most comfortable in the situation. So I guess what Lisa said rings true also. I think on some level about the context. It all goes together in an intuitive mush and my mood dictates a lot! Waving at Janet.

The only test I have for wearing an outfit out of the house is, would I be embarrassed to be seen in public in this. If not, then out I go, and don't think about what I'm wearing beyond that. I think this was originally my mother's test, and it's held up pretty well for me over time. I wear a limited number of silhouettes, though some of them are certainly not in the usual run of things seen in my locale, but I'm perfectly fine with that. I'm also picky about the fabrics I want on my body, and wear the neutral colors that please me. So I'm already 95% of the way there before I ask the question.

Jenn, I had missed your comment ... Love this approach; I think I will try this myself!

Hmm. You know what? I never run into people I know accidentally. Like, I never go to Trader Joe’s, which is probably where I’d see everybody, lol. I, for the most part, don’t think about this. But I do think about ‘milieu,’ especially because my hair is dyed vivid colours. If I go to the suburbs or out of California, I dress carefully and use my dad’s befuddled yet expectant expression with my best plummy tones. I go anywhere, from the ghetto to Gucci, but it’s with a careful balance of my personal taste and navigating the social mores of a place. And actually, the ghetto and Gucci have a lot in common and are safer than the middle places. Those middle of the road places, where people worry about their property values and police each other’s house colour... places where people are hungry for social acceptance from and yet also dominance over the larger society... those are very dangerous places and their children hunt in packs.

Like Angie and some others, I don't think about fashion in this way, either. I mostly use an inner barometer to evaluate outfits. There are exceptions when I occasionally wonder if I'm too old to wear something, but I usually get over that (or else pass on/don't buy the item in question).

TG - This made me think of that french saying that you have to "be at home in your own skin." If we extend that idea then not only do we need to be relaxed and confident with who we are, in literally our own skin, but also at home in the "skin" the clothing that we choose to surround us. As many have stated recently, I dress for weather, activity, audience always in mind. But my goal is always to be able to literally forget what I have on after I am dressed because I want to be so "at home" so tranquil, confident and at one with my outfit. To me the best mark of comfort is when I am not aware of myself or my outfit. To feel so assured and peaceful personally and sartorially, that I live outside myself because my inner voices are content. (and that's going some because I have a rich inner life!!) It does require that I plan outfits carefully and typically in advance with attention to hair and grooming, but when I'm done I rarely give my outift another thought. That kind of equanimity in all situations is a life goal!!

I’m with Rachy. There’s respect for the social setting while also telegraphing that you are not of the setting—like an anthropologist. I use this a lot at work.

I also think about what I need to accomplish. Do I need to cajole (soft furnishings in beige tones), intimidate (killer pantsuit and manolos), veg (Mickey sweatshirt and dogfaced slippers).

Love these posts Helena! I will dust off my story about how I ran into an ex at a local supermarket (our relationship was on another continent so it was a shock) while I was in the absolutely most awkward point of growing out my grey (so it basically looked like I had just neglected my roots too long). I didn't even see him - he calls my name and tells me I look exactly the same (a good 20 years had passed). Well I soon cut off my hair to expedite the growing out process, possibly affected by that meeting, but otherwise I dress for my mirror. I am my own worst critic, no other voices can compare.

I don’t do this generally although I do think about climate, activity and norms of the occasion concerned. I work on the basis that if I enjoyed wearing something and it was appropriate to the occasion that is enough. I try hard to do my own thing and not second guess myself.

I’ve said this before but where I second guess myself the most about how what I wear will be “received” by others is when posting here. It doesn’t actually affect WIW but might affect my decision to post an outfit. Not that I regard anyone here as a “frenemy”! Just that it can be hard to put yourself out there for evaluation by such a style conscious group. But I love the sharing of ideas that goes on here.

I have had the experience of feeling far from my best and inadequately presented and prepared. I have got it wrong (underdressed for a UK conference where I did not realise that in 30 degrees a black suit was still the expectation)..... and if I pop to the local shops in my running gear or lounge wear when I am sick I will always run into more glam acquaintances.

Some people always spend time to make sure their outfit or grooming is of a very high standard. I don't - reasons for including getting distracted by YLF.....

If I am planning an outfit I will always try and create something that makes me feel happy and at my best - but I confess that I sometimes don't think about it until 5 minutes before I leave the house needing to do a drop off or pick up.

If I'm not mistaken, your question has more to do with editing your closet (which pieces do I keep, which do I get rid of) rather than with planning an outfit for a given day. It's an interesting question. I've never thought of that criterion before. Maybe when it comes time to edit my closet again, I should use it and see what happens.

I do know that I tend to keep pieces around that wouldn't pass this test, and I don't love those pieces. I would rather pass them on, but they fulfill a practical role and so can't be disposed of yet.

I guess I’m more with Suz et al. It’s more me that I’m trying to please. It may be affected by others ( like wearing the stompy cobalt boots to a meeting with the difficult hospital executives, because the boots make me feel powerful in that situation) but I’m not worried what they’re thinking about my clothes? It’s my ideas they need to think about. So I don’t think it would help to think that way in editing my closet?
I’m still keener on the persona way of thinking.

Oh no! More navel-gazey (edging towards therapy talk) than you intended—you’ve just explained to me why, when I’m really pleased by a look, my thoughts turn to my family being blown away by said look. A benign interpretation would be that when my mom asked what Kate’s did (would you be embarrassed to be seen in public in that?) we generally understood it to mean would *she* be embarrassed, because we all knew I didn’t care. Moving right along...

“Daily life” can mean lots of different contexts. In some of them I’m more interested in giving a certain impression than others. Ideally, I’d love to get back to the point in my career where I didn’t gaf what others thought, because my work spoke for itself.

I did sort of run into the sudden change of circumstance you mentioned, but it was more wishful thinking than unpleasant. Walking into the mall to pick up something for my son who wasn’t feeling well this weekend, I realized I was wearing the same schlumpy combo as the last time I’d been there. I decided I was ok with it, because I wasn’t there to shop for clothes for myself. But then there were a model and photographer shooting ads for a certain store. It would’ve been fun to jump into some of the sets (none of which were marked off or guarded at all) but the thought of the resultant phots in that outfit wasn’t appealing, so I kept moving.

Fascinating to read the many thoughtful replies! I think my entire signature style is geared towards creating a bit of a softened superhero effect as part of my costume before I leave for the day. I have talked about this before and I think I am understanding now where it fits....here is it’s context! My profession is one in which I am meeting new people daily, and often the relationships have potential to be adversarial, frenemy like, and or have any level of power differential, typically with me sitting at the top. I try to be sensitive to this when I put together my outfit. Genuine Composed. If I am not careful, I become intimidating and overwhelming due to my stature, my personality, and my position. My role model is my Aunt Sylvia who always had it right. I wear a piece of her jewelry every day. The most important thing I try to emulate is not her signature style with clothing, it’s her grace, her polish, her etiquette, and her calm ease around people. I wish I had her humor! Her charisma was magnetic, and that is what I most admired and try to incorporate....probably poorly.

This is such a rich thread; I'm going to come back and respond more thoughtfully a little later ... but thanks everyone for sharing your thoughts; so appreciate it, and as usual its a trove of diverse wisdom.

Shevia, your comment really resonates "I am my own worst critic, no other voices can compare". So true *sigh* ... why do we do these things to ourselves?? xx

I can definitely relate to being my own worst critic! But I'm far more likely to be criticizing my own body in the clothes rather than the outfits themselves. I almost always think something along the lines of, "this would look even better if I just... (lost 15 lbs, didn't have such big boobs, etc., etc....). Sigh.

I don’t have style icons and don’t try to imitate anyone. I just wear what I like and what makes me happy. There are some situations when I prefer to blend in, like important work meetings, but in most cases I just don’t care what others think about my outfits. Ex boyfriends included LOL

Helena - I'm thinking your embarrassment over your bright clothing when meeting that woman suggests that bright clothes are not your true style, yes.

I have a similar thing happen when I wear prints out-and-about. I don't necessarily need to see a 'frenemy' (I don't think I have any of those!) to feel 'off', but if I see anybody dressed elegantly without prints, I immediately think I'm over-done.

Of course, there is always a niggle in my brain when I feel 'boring'.But I have figured out that just wearing 1 trend/new item seems to cure that for me.

Smittie, yes, I think that it does come back to this whole idea of 'what I like' and 'what I like to wear' and that the two things aren't necessarily the same thing. I just did an exercise on Pinterest today where I looked at my 'my style' board and deleted items that, when I really think about it, wouldn't feel comfortable in (or at least wouldn't feel comfortable in across a range of scenarios) and there were quite a few deletions, I must admit! I have a terrible habit of assuming what I like must be wrong and therefore I better change or at least improve it *sigh* ... it's inherited but I shall continue trying to defeat this beastly attitude!

I am applauding everyone who has the "I wear what I wear and deal with it" attitude to their style - this is the holy grail for sure, and so glad to be surrounded by women that have it. Some of the reasons I'm hearing are that you're true to your style, that you know it's a 'damned if you do, damned if you don't' scenario anyways, or that you just don't give a cr*p. What else is in the secret sauce, if I missed anything?

bj1111, that's a fascinating take on Rachy's thought - I definitely 'rebel' against the wealthy suburban mom uniform of Lululemon everything with a Louis Vuitton tote ... I'm not a brand-y person, as it happens (not that I'm against them, I just don't enjoy them for the sake of it) so this I am very comfortable with, even though it goes against the grain. Who knew my insistence on jeans was a social statement!

To those relating, thanks! And I can assure you, I would have 100% confidence in YOUR style for you, even if I couldn't do the same for myself!

Brooklyn, that's so interesting, and I was initially going to say, I never worry about outfits I post, but as I type I realize, yes, I do self-edit too, because most of my outfits are too boring to post, even though in truth these are probably some of my favourite outfit (for example, today's navy linen t-shirt, jeans and cognac flats. Happy place but not an exciting photo). However, as you say, this is not because of the group per se but rather the subject interest - I (usually) only post outfits that seem sufficiently 'style-y' given the interest of the group.

Thanks ALL for a fascinating and enlightening discussion - as always.

See, this is interesting - should you use fashion to counter that side of you, or to express it - so people see what's coming, in a manner of speaking?

I am the opposite. If I am not careful, I can come across as milquetoast and "nice", when in fact I have extremely strong opinions, ethics (aspirationally at least) and ideas - which I was burned for in the past and learned to keep quite controlled, for better or worse. I am not to be underestimated - but often am BUT people don't get to see this often - it's on my terms and has taken more than one person by surprise. (I am quite nice though, btw lol!)

So this makes me think:

• the 'my style' that I'm comfortable in in pretty much all circumstances is the more understated, quiet version (e.g. the neutrals, the simplicity, etc.
• the 'my style' that I'm not comfortable with is the bolder, more opinionated piece (e.g. a strong colour statement or accessory, say) which is also genuinely 'me', just not the me I'm happy sharing haphazardly (thus the particular discomfort with peripheral or uncomfortable acquaintances)
• and assuming above is true, is it better to honour the first point, or be bolder regarding the second point?

Or am I overthinking the whole thing?!?!? Down the rabbit hole I go!!

Well now, THAT is a problem I have sometimes... being seen as ‘nice’ or ‘laidback’. You can do you, but not necessarily in my space. I can be quite tart about things like that... and ohmigosh, I created my dog. Lilypup’s nickname is Hall Monitor. She rolled her classmates twice her size for playing in class... but back to me, that’s a tough one. I can only dress severe for a couple of days in a row and then I have to jail break my bright, happy clown clothes...

@TG - when you self censor (your outfits) do you feel like you are conforming and thus giving up a part of your identity, OR are you infiltrating so you can subvert? In other words is the motivation (to dress conservatively) internal or external? I believe there are circumstances when it might be appropriate to reign in personal style and play along with group norms if you have an agenda, or need to make a point on some other level. You don't want your clothes to be a distraction.

On the other hand, I've never seen you post any pictures of outlandish outfits, so find it hard to believe that you would be judged adversely for what you choose to wear. I don't think a raspberry t-shirt vs, say a mariner, is going to get the 'side eye' !

I like the idea of asking if I’m presenting my best self - and clothing is part of that choice. It’s also been a way for me to set aside some not-quite-right clothes that have filled my wardrobe in the past. Yes there are days when my best self is in lounge wear at the coffee shop, but in most cases it’s a motivator to spend the time to choose the outfit, do the hair/makeup, rethink the shoes etc. if I’m presenting my best self, I’ll be happy and confident regardless of who I see, even if it’s just me in the mirror.

Sounds like I should’ve been stronger in that last sentence. Trying again:
Although I don’t want people to feel blown away by me, I also don’t want them to pat me in the head and think what a nice little drone I am. Now that I’m getting older, people make that “nice” assumption more often. I don’t like it, and it doesn’t fit. So on the one hand, dressing in a way that lets people calm down about Ms Tough is a good idea, but on the other hand I need to be careful not to look like a “soccer mom” with all the baggage captured by that term.

FI - that's what I understood from your statement

Carla, I lol'd at your comment! So true ... I think it's fair to say this is 100% internal; my brain is a strange and daunting place lol!

Thanks ALL for comments ... and hope this has been interesting for all and not 'all about me' (and my obvious neuroses haha!)

I often have the same disconnect you do - that what we like and feels true sometimes doesn't line up with what we want to wear.... it's a bizarre thing. This has been super helpful and gives me lots to think about!