More about missteps: Trying too hard

Ah, astute commenters, you make me think, which is all the reward I need.

On a recent post about missteps, Alison recounted the criticism one blogger received from her WIW post in which she wore leather trousers and overlarge white sneakers. She received compliments but also some negative feedback, and then defended her choice of the sneakers as "unexpected and modern."

Alison asked, 

"Is one person’s misstep another’s ‘unexpected and modern’? I thought the leather trousers looked great, another opined ‘trying too hard’. Many thought the sneakers were a step too far but the blogger had her own theory."

In reply, I linked to this 2012 post about WIWs, and today address a related topic, "trying too hard."

That criticism "trying to hard" could contain various judgements:

1. She is wearing clothes too young, trendy or outré. The charge nearly always carries the subtext "for her age". It assumes that with age, certain things are off limits for most women*; the usual code word for a failed attempt is "inappropriate".  While I believe a few styles are better left as memories, it is usually the result of a curdled brew of ageism and misogyny. 

*Going for the exotic takes a gifted eye, as shown by Dame Vivienne Westood in one of the last photos of this extraordinary designer. 

2. She is overdressed for the occasion. Around here, we do not wear (fill in the blank): a chic trouser suit to the supermarket, a dress to a kid's soccer game. The subtext is, "We don't try, and you trying makes us look schlumpy." Sometimes this charge is a screen for the accuser's inability to refresh a wardrobe, or wear certain styles.

Often, it reflects the locale. Here's an example: I sent this photo to our sons when I visited our old 'hood last year, saying, "I never saw anyone dressed like this when we lived here!" But at the same time, I thought the young mother looked fabulous. When we moved into the utterly ungentrified Leslieville neighbourhood in Toronto in 1986, no one wore a vintage ruby coat to push a pram on a Wednesday afternoon, and few do now, it's heavily LuluLemon and All Saints.  

3. She is overdone. She has piled on too much makeup or effects like two-inch press-on nails; she is a hair dominatrix, beating it into unhappy submission. The scarf is tied in a fussy complication. Perhaps, for the accuser, there's too much colour or pattern. That judgement is bound to be subjective, and informed by location, class, and ethnicity.

How do you not look like you're trying too hard? We might consider the opposing concept, sprezzatura. The guardians of magnificent sartorial style, the Italians, minted the word which means, "an appearance of nonchalance, despite the effort that went into what one does."   

Two looks captured by Scott Schuman (The Sartorialist) show the attitude:

Photo: Scott Schuman, The Sartorialist

Lessons: Any monochrome ensemble, unless it is neon, will ratchet up the S-Factor. 
The "pop of colour" is not a sprezzatura staple. The clothes worn by this woman sitting on her stoop in New York would work for any age; you might also wear tones of the same colour. And the pearls, we know! 

Madonna, this Milanesa! I have returned to this photo several times, for its ease and elegance. Here, colour does carry the outfit, but softly:

Photo: Scott Schuman, The Sartorialsit

To quote another Italian, journalist Renata Molho: "Not too many beautiful things at once." Sprezzatura rests on restraint, an aesthetic that leaves room for breath.

Sprezzatura is not solely the property of the urban woman. This photo is from Margaret Howell's Instagram. One way to look like you don't try too hard is to outsource the job to a designer known for walking the fine line between simplicity and interest, as she does.

Alison also said of the blogger, "
Bless her, she put herself out there and in her mind had achieved the look she was after", and asked, referring to the blogger's defence of her sneakers, "Is one person’s misstep another’s ‘unexpected and modern’? 

I thought of Diana Vreeland, who said, "We all need a splash of bad taste, it's hearty, it's healthy, it's physical... No taste at all is what I'm against."

For some women, self-expression is paramount, and they do not care to conform to someone else's standards. The last word belongs to this young woman. You can see the snow on the street, but not last weekend's -33C cold—and there she was in a mini, open jacket and bare thighs! (I suppose the white thigh-highs were a concession.) I said, "Girl, I have to take your photo!

She said, secure in her self, wholly inhabiting this look, but two words: "Thank you!"




Jay said…
In some cultures, not making an evident effort to dress for occasions can give serious offence.
You just can't win!
Jane in London said…
I must confess that, although my own style is now rather low-key (though I had my moments when younger) I have a bit of a soft spot for older women with over-the-top style. I think Vreeland was right on that score.

There's a wonderful account on Insta that has admiring photos of older Milanese women going about their business in their Versace, voluminous hairstyles, high heels and gold jewellery that you could probably sell by weight. Sometimes with a cigarette on the go, too. I find them totally joyous, though I would not have the time, money or desire to adopt their style.

During an earlier period of my life I met lots of older middle eastern women who also adopted this very high-maintenance, sophisticated style. I found them mesmerising, from the rattle of their fabulous stacks of designer bracelets to their perfectly coloured and coiffed hair.

I suppose what all these women have is unassailable confidence in their own style. A more nervous woman would look as though she were trying much too hard - but these women look as though they don't have to 'try' at all.

See also Joan Collins, who unapologetically rocks the same old 80s glamour with tongue firmly in cheek and clearly doesn't give a fig for what anyone else might think of her style. Game old bird, as we say in the UK ;)

Duchesse said…
Jay: You hit a nerve! At a son's wedding, a male guest in his early 30s came to the ceremony in jeans, running shoes and a well-worn t-shirt. When I asked E. about it, he said, "He wants to be 'a man of the people', he works for a social service agency that addresses poverty and refuses to dress up." His wife wore a pretty dress. (The wedding did not specify a dress code; he would have been fine even in trousers and a collared shirt.) A wedding is not merely a party, it one of the most important occasions we attend, and to show up in clothes that look fit to wash a car in is to ignore that. The young man could have picked up a shirt and trousers at a thrift store or borrowed them, if he wanted to reduce or avoid consuming. I wanted to say that to him, but I did not trust myself to be civil. Also, (as I told my son) I have been to a number of weddings held and attended by persons with little money, and they all dressed in their best clothes.

Jane in London: I love those over-the-top women who manage to go to the wild side with their confidence intact. Some of the women on the "Advanced Style" blog pull that off, others do not. But my deepest reverence is reserved for the more discreet dressers—as Molho says, "not too many beautiful things at once"—who are artful with colour and fit. Vivienne Westwood could dress unconventionally but her tailoring was impeccable.

Joan Collins is an entirely different exotic bird; quite a bit of "alteration" there , versus Dame Westwood's tailoring.
Maudie said…
Thoroughly enjoyed this post. What I admire on someone else may not be for me. I have opinions but try not to judge. However I do struggle with the distinction. How do you distinguish between opinion and judgement?
Venasque said…
I love this post. That Milanesa - yum. Older and yet achingly chic. If I attained that level of chic, I could die a happy woman. I too have a soft spot for older women who have that "une femme d'un certain âge" look. A bit out there, edgy, but not ridiculous.

I must say you showed amazing restraint re the wedding attire. I don't know if I could have held myself back. Does he thing dressing badly makes him one of the people? It just makes him look badly dressed and in my view, disrespectful of those he purports to help. Does he think poor people dress, I guess in his view badly, because they want too? That's what they have, so that's what they wear. Looking like a shrombolata does not get you to heaven any faster.
Anonymous said…
I enjoyed this post.
Back in the 1960s, in Seattle, there was an absolutely flamboyant man named John Doyle Bishop with a fabulous women's clothing store downtown. More pricey and upscale than most of us could ever hope to patronize.
He had a spread in a local magazine, one outfit was an over-the-top elaborate suit (maybe Chanel?)
Someone asked him where, exactly, this outfit could be worn. His prompt response, "To church in Beverly Hills."
We can all use a little Beverly Hills in our lives
Duchesse said…
Maudie: I was happy to spend a half-hour reading various explanations of the difference, and you might, too. One I liked noted that an opinion is a belief or view that need not be backed by factual evidence: "Frosted blue eyeshadow looks tacky". An opinion can be based on only one's own perspective.

Judgements raise the bar as we expect them to be at least partly based in facts, but they are also derived from our feelings, attitudes and values. Usually, when a person delivers a judgement, they present a reasoned argument that provides grounds for their judgement. In formal settings such as debates and court, a judgement has to withstand scrutiny about the validity of facts and knowledge.

IMO many women in the Passage were socialized in their youth to voice neither opinion nor judgement, especially if negative. Girls were expected to display "nice" behaviour: praising, giving compliments, smoothing over dissent. The unintended result was to create at least one generation that at times struggles to express dissent, for fear of being called "opinionated" or "judgemental".

We should talk about this further, Maudie. I am interested in your thoughts.

Venasque: I regret holding back, but the groom said when I told him that he was glad I did. This couple had travelled a very long distance to be there. The man and his wife were friends of the bride. I do not think Jeans Guy thinks poor people dress badly, I think he thought E's male friends, who came in sharp suits, were pillars of capitalism and their clothes sent the message that money meant a lot to them. (Some of them were by then successful young entrepreneurs but a few were struggling, and they had dressed up, too.) Somewhere in the depths of this blog are two posts I wrote about snobs and reverse snobbism (BONS_ and I guessed that Jeans Guy might be a BONS.

Anon@11:57: That's... priceless! My LA girlfriend used to call it "Beverly Thrills".
Ronni said…
Duchesse! I love how you are becoming the Bill Cunningham of Montreal! Great street photos
Anonymous said…
I am going to pose a question as I am not sure what to do.
And seeing the picture above of Dame Westwood, prompted me.
When that was taken, we could say “exotic dresser.” In the last few years,
here in the USA, I “think” as I am not completely sure, but it is no longer
“ok” to wear something from a culture/people into which I do not belong.
I am a mid-50’s, white female with almond hooded eyes that look Asian when
I smile. At least other white friends say that about my eyes. Question: I have lived in Seoul,
back in 2008, and really like the handbok style of women’s top & skirt.
I’m short and a size 10 in skirts so definitely not petite. Would it be not appropriate
to wear handbok top & skirt if I am not Korean or a part of a Korean family?
Is this similar to, if I were to wear dreadlocks?
Ok look forward to your reply.
Duchesse said…
Mimi: My reply will be a full post but for now, please note the photo of Dame Westwood is very recent, as I stated, one of the last taken before her death at the end of January 2023.

Look at her balled fist. She was no stranger to the politics of personal presentation.
Anonymous said…
Ahh, my mistake, I had no idea it was a recent picture.
My apologies. mimi
Bunny said…
This comment has been removed by the author.
Mardel said…
Many years ago, decades really, I was shopping with a couple of friends. One tried on a couple of dresses the the other two of us felt she looked better in dress 2 over dress 1, although both fit her beautifully. She preferred dress 1, and questioned our judgement, stating that the dress made her look the ways she wanted to look, whereas she felt we were influenced by a narrow precept of style and culture. A intense discussion followed, and I have always remembered it. I increasingly admire women who dress for themselves, even with missteps, although I'm not really sure what a misstep actually is. Who is miss-stepping? The wearer or the observer? I'd probably consider the wedding guest to have committed a misstep. As to other choices of stye and proportion, I increasingly think it is good for people to be more adventurous than my particular generation and social set was trained to be. Who knows?
Duchesse said…
Mardel: What a misstep is is, essentially, a mistake. I think we have all bought something with fizzy, happy certainty, put it on later, and thought, Uh-oh. Or, someone else has, which is when the buyer can feel defensive and upset, as in the WIW posts when commenters do not unreservedly praise her.

How I wish I had saved the link to a woman who posted at least 8 shots of missteps, with hilarious commentary.

Ultimately, yes, Mardel, the buyer decides. Recently two friends visited Montréal; one wanted to shop for resort wear and tried on a very bright midi dress she was "sold on". Friend and I both said, the colour drains you and makes the dress look cheap. She found a number of things in same shop that looked terrific. She could have bought the dress anyway, but she was so impressed that her discreet, introverted friend was adamant, that she listened.

Mardel said…
Oh, I wish you had saved that link as well. And how lucky for your friend to have you for your thoughtful input. I make missteps all the time, sometimes about color or style or fit or all three, and often thinking that x will look good with y when it really doesn't. I don't think it is that I never learn, more that I just never stop experimenting. Even though I have lived in Tennessee for over a decade now, there I are things I could wear in NY but cause raised eyebrows here, and I am unwilling to blend in completely. As to that hydra that is the internet, well it is difficult to discern what is well meaning and what is not, either in positive or negative responses.

Anyway I love your posts because they always make me think. And I am a woman who lives perhaps too deeply in her own head, so I always wonder about deliberate missteps, ie, what is this person saying or trying to say? I look forward to more posts, and your response to Mimi's question as well. As to my 80's shopping experience, it was not an issue of color or fit although perhaps style. She wanted a dress that made her look like something out of a Botticelli painting. We wanted the dress that made her look like a tough 80's vixen. I always admire women who find their voice and make it work for them, and your photos illustrate this perfectly.
Duchesse said…
Mardel: The White Lotus character, Portia, is dressed in "deliberate missteps" but that is the costumer's decision; she wanted Portia to look like someone whose choices are a little off, in contrast to the other American women characters. Portia's slightly haphazard style sense amplifies her character's not-fully-formed self and good-hearted (and good-time) nature. They tell the viewer the backstory.

I wonder whether a woman in the Passage would want to make a •deliberate• misstep, as in, "This is not good on me but I'm wearing it anyway". I can only remember a few bridesmaid dresses, which were not my choice but I had to wear them.
Allison said…
Oh I am rather late to the party but just wanted to say that when I threw that comment about the blogger out there I was rather hoping Duchesse would take it for a run!! You did! I am also so very happy to read the dialogue that has since developed re: missteps, opinions, judgements and the like.
When I look at Vivienne Westwood I am reminded of something my mother used to say. “you wear the dress it does not wear you” I have come to believe that she meant wear what you like but underpin it with the right attitude. I have seen some pretty outrageous ‘get ups’ ( another motherism:) over the years and those that garnered the most admiration, even begrudgingly were worn with attitude. Case in point, my darling cousin choosing to wear her bespoke teal suede bustier dress with matching jacket to our grandmother’s funeral (a large formal Catholic affair.) Her WIW moment might have been seen as the fashion misstep of the year ( or statement of the year?) and yet it fitted her beautifully and was worn unapologetically. Maybe that’s the key? One should make no apologies for one’s sartorial choices. In my cousin’s defence it was likely the best outfit she owned at that time so she dressed up and showed up. Having taken a waitressing job at a night club her wardrobe consisted of tight jeans and skimpy Tshirts but the tips were enough to start her on the road to owning a considerable amount of west Toronto real estate and an enviable financial portfolio.. did I mention ATTITUDE..At 62yrs stepping into her vintage Stingray wearing leather leggings and thigh high suede boots, frankly m’dears she still doesn’t give a damn what anyone thinks:)

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