The style dilemma: go for one true safe style or experiment with different options and take risks?

by Sylvia


If you have a look at some of the main style icons like Jackie O and Audrey Hepburn, their eternal style is characterized by a very elegant look. Simple lines, not too many frills and signature pieces (like Jackie O’s sunglasses and Audrey Hepburn’s shawls). As you know I am a fan of both ladies.

In some of the style books I have read lately, very often examples are given of ladies who have very few but high quality pieces and wear them repeatedly. They have a clear signature style and exude elegance and class. I admire that.

I also love women like Iris Apfel,  The style Crone and the Advanced Style ladies who have such a unique style and are constantly pushing their boundaries with new styles and ideas. I love that too.

A style dilemma

So here is is the dilemma that you may or may not have also. Although I would love to be this really classy woman with just a few super high quality pieces and a clear signature look, which in my case could be dressy pants with a classy asymmetrical top, I am constantly looking for the new and different. I hop from one style to another and I love fashion. I simply cannot go for just one style.

In the process I risk not being labelled as stylish, I will probably never bceome a style icon (just kidding), and some of my creations will be absolute fashion disasters. (certainly when you look back on them in 10 years time). If anything, as I get older, I want to be MORE daring, buy more unique outfits and take even more risks. This goes completely against the ‘signature style’ and ‘elegance’ so advocated by many of the style professionals.

Then again, on other days, I feel like sticking to a minimalist style: concentrate on the basics and just accessorize with a few special accessories. Keep it super elegant and chic. I think at the end of the day, that’s truer to my nature.

How to solve this?

It’s up to you if you consider this an issue. If you want to fully consistent with you style you may have to play it safe and go the chic and elegant route.

Or you can just accept that you are all over the place. Perhaps it does not need to be ‘solved’ and you and me can just have fun with our clothes.

As for me, I’m not yet able or willing to stick to a consistent ‘safe’ style. I will just go with the flow and buy clothes on impulse and intuition together with planned ensembles and essential basics to make sure that I have a versatile wardrobe. I feel that in essence I’m a minimalist, but a minimalist who likes interesting details and is always looking for great lines and silhouettes. I’m always attracted to new trends. I wonder if I will ever truly find one style that I can absolutely stick to.

In the end our style will always evolve.

That is a good thing because fashion and dressing yourself needs to be creative and exciting. At the very least I think it is important to truly understand yourself. To really understand your body and how you can best compliment it with the right clothes. It is also essential to choose clothes that suit your personality!

It’s not absolutely necessary to have a clear label for your style and stick to only ‘safe and elegant’ items. When you understand some of the key points about yourself and what works for you, you can just go with the flow. If you have trouble doing that then I highly recommend my my style course which is sure to let you discover your own unique style or cohesive style elements and will help you to dress better.

I like to hear from you!

Do you have a very clearly defined style? Or do you jump from one style to the next? How important is a cohesive style to you?

Photo above from the Hussein Chalayan Spring / Summer 2013 collection, who will be coming to Singapore’s Audi Fashion week this week, together with Carolina Herrara, Colette Dinnigan and others. For more info and tickets you can check out their website. I will attend a few shows so will be back with more info and impressions of Singapore’s major fashion event!

{ 43 comments… read them below or add one }

1 Jeanne

Sylvia – I enjoy your blog very much. I personally think that people with one singular style can become a bit boring and predictable. Better to try lots of different styles and mix them up! I know my level of fashion risk has been tempered by age to some extent. NOW I have to think 1) do I like this style risk? and 2) is it age appropriate? (i.e. is it too short, too tight or just silly-looking?)


2 Sylvia

yes, that is pretty much how I think. Thanks for your feedback Jeanne!


3 Sophisticated Lace

I totally agree!! While I really admire those iconic ladies that made themselves famous with a certain “look” (which is totally what seems to get people noticed in the style blogging sphere as well), I don’t think I could ever stay devoted to one style. I love to many things-from minimalism to crazy vintage stuff to neon and tulle skirts. There are quite a few styles that I absolutely hate, but aside from that I’ll try almost anything. And yeah, I never really think of creating the perfect wardrobe-if I see something that catches my eye, I’ll get it, even if it means having to wait several months until I can acquire some more pieces for it to actually look good when I wear it.

Sophisticated Lace


4 Sylvia

Nice to hear your feedback. Sounds like you have a very fun style!


5 Natalie

I don’t think I have a clearly defined style, but I’m realizing I need to listen more to that internal voice that just says ‘no’ sometimes when I’m considering a new trend, because deep down in my gut I just know it’s something isn’t right, I suppose. Perhaps my style is more defined than I think, though, because sometimes, while shopping with my husband, he’ll spot something he’ll know I’ll like before I even see it. I would like to be known as someone with a classical style rather than someone who desperately tries every fad.


6 Sylvia

Yes, it’s about finding that right balance. Most of us will have a defined style in some way. The question is how much you deviate from that and how often…


7 Rebecca

This is a wonderful post Sylvia. I also love to see people with very creative style but in the end I feel most comfortable with what I call an edgy elegant way of dressing. I love beautifully tailored jackets and body conscious (but not tight) clothing with great accent pieces. I have been very impressed with your style and that of the many stylish women you have featured on this blog and get many ideas from their way of dressing.


8 Sylvia

I like your description : edgy elegant with great accent pieces. I think that’s what I’m going for as well. I want things just a bit different.


9 Chicatanyage

I would say that I have a distinct style, probably classic with a twist. I find that if I stray too far from this it does not work. Having said that I do update from time to time, cut of trousers, jackets and colours can change.


10 Sylvia

Some women are very good at sticking to a distinct style and I admire that too. I just think that some of us (me!) also need to accept that they can’t do that and it’s ok to stray and take risks. That is what keeps us happy. It’s always important to understand what is right for you personally. Thanks for your feedback!


11 Aileen

I’ve been in Italy for the past three weeks and missed your blog, but am catching up now! This is another brilliant article Sylvia and has made me stop in my tracks and really think about it. It will be interesting to hear what everyone else says.
I am now going for the stylish, classic and chic with a little twist, but not too much. My ideas have changed so much since I started following your blog and when I brought out last year’s summer clothes recently, I realised just how much my ideas have changed!
I have completely gone off anything with frills and too much pattern and now want to have a pared down sleek/stylish look.
It was interesting watching what women on the streets in Italy were wearing too. Most ‘stylish’ women wore skinny jeans with a short jacket and longer top underneath and either long or short boots and of course a handbag with long handles hanging off their shoulder!
I only saw two women wearing skirts.


12 Sylvia

Hi Aileen. Lovely to have you back and how fabulous that you had 3 weeks in Italy. You must be so inspired. Interesting that they don’t wear skirts….


13 Aileen

Hi Sylvia, nice to hear from you and yes, it was a very interesting trip. Rome, Pompeii, Florence, Pisa and Lucca a few of the places we visited. The shops were fantastic, wonderful shoes and bags and all the designer shops mixed in with other less expensive ones.


14 Sylvia

All my favorite places…. I could go there each year!


15 Greetje

I should have sent you shopping for my chain necklace (the yellow one) in green and red. haha.


16 Aileen

Ah, yes Greetje, you were a bit slow there 🙂


17 Judy Carpenter

Several factors go into my style. Boredom, limited budget, body type, and some others. So I dress the way I feel when I get up in the morning. Sometimes it’s a dressy day and sometimes it isn’t. Sometimes there is jewelry, sometimes not. Etc. I don’t think I like any one style enough to stick with it. I do, however, try to stay with my interpretation of fairly current things. At my age, it gives me joy to feel a bit with it.


18 Sylvia

Love your last sentence Judy! Thanks so much for your feedback.


19 Marie Dowlng

I’m interested to know what age group you mean? I’m49 this november and have a 5 year old grandson. I LOVE clothes, and feel incredibly inspired by others ( although i probably don’t take enough risks). I guess though that as i age, i may feel less inspired….. Hope not!


20 Dez Hanna

This is the perfect topic, one that I asked myself and struggled with since I passed 40. As we age I think each of us have an Ah Ha! moment, where we figure out we can’t wear certain styles anymore and some styles we need to edit in order to make them more age appropriate. I’m in a transitional period in my style life and just trying to figure out who I am now, in my youth I was never classic, but always tried to be trendy. I think I’m more classic with a twist. Great thought provoking post Sylvia.


21 Sylvia

Thanks for your feedback Dez!


22 Kathleen Lisson

I notice that there are some hot-button words in this post – safe and boring versus unique and pushing boundaries.

Jackie Kennedy was a trendsetter in the White House, with a style that was light years ahead of her predecessor in the White House. Have you seen photos of Mamie Eisenhower? It is interesting to see how Jackie pushed the envelope in her time in the White House, from sleeveless gowns to strapless.

Why is her style safe and boring now? Because she wore it so well – it perfectly ‘fit’ her personality.

I want my personal style to be elegant and classic. It looks “safe” and “boring” to the eye when it is done right. Is it safe? Perhaps, but I get so many ladies telling me that they “just don’t look good in hats.” But a few generations ago, every woman wore a hat. Have everyone’s faces changed, or is wearing a hat a gutsy style statement?

Nowadays, most women wear jeans and a sweater, t-shirt or loose fitting ‘comfy’ clothing. Is my style unique? Can everyone look poised and feel fabulous in well-tailored classic clothes? Maybe elegant isn’t so “safe” after all.



23 Sylvia

I just reread the article and I don’t mention ‘boring’ anywhere. I’m not implying at all that sticking to one style is boring, although some women can get so stuck with their style that it could become that. Safer yes, because you know what you like and you stick to something that works. But someone like Jackie certainly took risks. She was able to stick to her style all the same, even though she did resort more to less daring options as she got older. It certainly was never boring.
I absolutely think that your style is unique and by incorporating hats it certainly is never boring!


24 kathleen lisson

I included the responses I read in the comments section as part of the “post,” because your reply indicated that you agreed with her perspective.
I am encouraged by this discussion, as I enjoy all the substantive fashion discussions on your blog. It is one of the few blogs where the comments section is as informative as the blog post itself, because you have gathered such a great group of thoughtful women together.
I think as Americans we are adventurers and see the word ‘safe’ as a negative. I suppose their are many ways to use the word safe – Laudree macarons, Paris in Springtime, a hug from a best friend. I feel safe in my husband’s arms. When an act is performed with expertise and perfection, it is safe. It is sure to be enjoyed by others. I like that definition of safe for my classic style.
For me, the best part of my late thirties is that I can find the style that flatters my body, who I am as a person, my career and after work interests and my sense of beauty and stick with it instead of looking at other women with different bodies and thresholds of pain (towering shoes) and trying to copy their styles (that’s what I did in my 20’s, follow trends and try to copy others).
For me, being stuck is very exciting. When I bring a new hat or item of clothing home, it will do its duty and make my wardrobe even more chic and stylish. For me, shopping is so exciting because I have a well edited collection of clothes, and each one made me a little giddy with delight on the day it was added to my wardrobe!
Thanks for encouraging me to think about the logic and feelings behind my personal style!


25 Sylvia

Very thoughtful comment Kathleen. I very much enjoy your definition of safe and ‘being stuck’.
Yes, I like to write these articles that encourage discussion, but of course I need to be careful with choosing my words as I certainly do not want to offend anyone’s style. Since English is my second language, the words available to me are still limited, so they don’t always have the right nuance.
I guess I was describing that for me, I tend to get bored when I keep choosing the same kind of things. But I also see that this does not hold true for others at all and that their choices and way of dressing is not boring at all. In fact I can truly admire those that can stick to one style.
Thanks for sharing that point of view and articulating it so brilliantly!
It all comes down to really understanding yourself and staying true to your personality as you do so well.


26 Kathleen Lisson

I totally agree!


27 Greetje

Kathleen has a point I think.
For the rest I am the same as you Sylvia. I would like to have one elegant style, but it does not allow me to play around with clothes so much. I am famous for my “fashion failures”. As I do not have “the eye”, like Ann in your previous article, I sometimes get it so wrong haha.
But other women relate to that because we all make mistakes. Exceptions to the rule are of course the great creative ones.
So I know that black and white with a bright colour is one of my signature styles, chuncky necklaces is another. And by trying I sometimes stumble upon something that looks fabulous on me. Out of my comfort zone.
(By the way.. I am off to Paris. So you won’t be hearing from me till Sunday.)


28 Aileen

Wow, lucky you! I’m sure you will find something wonderful to add to your collection of beautiful clothes and accessories. Have a brilliant time xxa


29 Sylvia

We all do Greetje (make mistakes). Don’t believe for a moment that everyone gets it right all the time…
Enjoy your time in Paris Greetje. Take pictures! You can’t get a better background than that….


30 Annette

As you know my style, Sylvia, I feel most comfortable in my elegant style.
For some women “elegance” or a “sophistcated style” and “feeling comfortable” may not go together but I feel “uncomfortable” wearing jeans, sweater and sneakers and prefer dressing up jeans with a blazer and pumps.

I agree that style does evolve and I get a lot of positive feedback since I am wearing colours opposed to black and neutrals all the time (still love them though).

Yes, I do have a clearly defined style and wouldn’t take a risk.

Lady of Style


31 Celia

I have just found you blog Sylvia, and I love it! It’s great to see that women from all over the world share the same doubts and fears … It’s not easy to find a style, taking risks is part of the process, right? Greetings from São Paulo, Brazil – Oh, I have been to Singapore in February, such an amazing (and hot!) city! Love to see your pics! 😉


32 Sylvia

Welcome Celia. Great to have you here and thanks for your feedback!


33 Lorraine

I would like to take risks but I find that I have to dress to my shape and that certain things suit me and others don’t. I also have to wear practical clothes a lot of the time. Within those constraints I am happy to take risks with colours and patterns though!


34 Sarah

I personally would feel bored and sad if I felt I had to stick to just one look, however elegant and stylish. I express all the different aspects of myself through my attire, and I dress according to how I feel and what I want to convey at the time.

Funnily enough, I do like minimalism and I do enjoy wearing a minimalist look from time to time. But not all the time. Sometimes I want to look super-chic. But not all the time. Sometimes I play with grunge. And so on.

Incidentally, one person’s stylish is another person’s boring/snotty/trying too hard/too sloppy/frumpy/age-inappropriate/etc — however you dress it won’t please everyone (or seem stylish to everyone) — so you might as well dress primarily to please yourself and not worry too much about sticking to one style if that doesn’t give you joy.

I think it is a mistake to refer to wearing a variety of styles as “all over the place” or “jumping from one thing to another”, because those phrases carry rather negative connotations, as though those who enjoy wearing different looks are flighty, making random choices, and if we were proper grown-ups we would have matured into a single signature style. I have no problem with signature styles for those who love them, I just don’t accept that there is anything better about having a signature style vs creative style experimentation or even simply dressing according to mood.


35 Sylvia

Hi Sarah, Yes, you are right. You can never please everyone so the most important is to please yourself and have fun. You are also very right about the negativity of the prhases I used. Let’s just refer to it as eclectic. Sounds much more sophisticated!


36 Marie Dowling

Take a risk for goodness sake! As they say, “you only live once”, so my philosophy is. To show the world who you truly are. There’s no use having regrets!


37 Lisa

I am probably more safe than flamboyant if you look at the tailoring of my clothes. But I am more flamboyant than safe if you judge me by the colors I wear and the way that I combine them. I think that appeals to both the economist and the artist in me.


38 33

this is also my struggle. as much as i would love to devote to a singular style as my “signature”, i am too often tempted by the variety.

part of fashion is the fun factor as in role playing. as my moods swing from boho to sporty to preppy to romantic to cute to wall street banker to 50’s housewife then back to boho i am glad that i have what i need in my closet to fulfill my fantasy.


39 Sabina @Oceanblue Style

Have always felt if you need the clothes to get some attention I would have to work on my personality a bit more 🙂 No seriously I sort of agree with you as far as playing it safe is concerned. It might get boring and mean there is a lack of style and inner determination. But the same is true for the opposite (as mentiioned above) So I guess it comes down to personality and what it is you want to show/demonstrate/or be. Elegance can be a uniform which are meant to eclipse the person wearing it. So being a 40+ fashionblogger I have been tru all stages of style and am getting to closer to really self-determine what I want to wear and how and feeling comfortable. That is why I try to add some edge to anything I put on. Love that topic. Sabina @Oceanblue Style


40 Jodie filogomo

I have always had a hard time with the question “what is your style?” And I’ve decided that to say one style is mine is too one dimensional! I think it’s fun to dabble with different looks and items!! Hopefully my personality is multi dimensional and so shall be my clothing style! jodie


41 Irmin

hi Sylvia, how very right you are! I often wonder about this dilemma, shouln’t I stick to one sort of style more? But then again there is simply so much I like. And I like to have the choice depending on my mood. I compare it to food, there are things I do not eat but I do eat and try out most things!


42 Kim Martin

Sylvia – I love your blog, & are now following some of the other blogs you have featured. I’m over 50, & have always had my own style, as my mom used to say. As an V-shaped woman, jeans have never fit me well, I just don’t have hips or a bottom. By the time jeans fit around my tummy the bottom is horribly baggy. I’ve figured out that leggings, lose flowy pants, & skirts work well. Skirts especially show off my long legs, I’m 5’8″ & with heels even taller. I totally agree that everyone needs to find their own unique style, what’s classic for one body type just won’t do for another. “Classic ” jeans w a great top doesn’t work for me. But it works great for others. The old saying “just be yourself” still holds true.
Jackie & Audrey wore what worked for them. I have seen pictures of Jackie when she was married to Aristotle O’Nassis. You can see she experimented w different styles too. Like all of us, she experimented w what was in style at the time & went with what she liked. That being said, thank you for your blog, & all the insight you show. Your constantly giving me new things to think about.


43 Sylvia

Thank you for your lovely feedback. It’s so nice to here that the blog inspires you and gives you ideas!


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