7 Top Tips to What Dates and What Becomes Timeless

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After a recent discussion with the Evolve Your Style group members, when deciding what to keep and what to throw out (because it is dated), I was asked about what is dated and what becomes timeless.

I thought I’d ask one of our group members and recent Stylish Thoughts contributor Lisa White share her thoughts on this topic as she has clothes that are decades old, but have become timeless.

Here is what Lisa had to say:

I am still trying to crystalize why certain pieces transfer better. I think I ended up with some as I tend to purchase fewer items but really expensive items. My first paychecks went into layaways at a local boutique (before credit cards and the internet were invented) and I started buying Cacharel, Armani, Christian Joss at the beginning of their careers. Those pieces lasted. Also, some of my western belts..now worth a fortune. I still don’t understand exactly…I sense it, but it is still a little fuzzy.  

Lisa White

I understand some items become timeless. What I am grappling with is what makes a TREND leap into timelessness. It happens….like ballet flats (the normal kind with round toes), or pajama pants. I have a feeling kimono tops/jackets/dresses will make the leap depending if there is not a lot of trendy neon color on it. Certain looks get re-cycled and I am wondering about what timeless qualities BOHO (if any) will leap.

Are maxi skirts going to make the leap? If so, which styles will make it to timeless…the simpler less detailed? The streamlined?? The Southwestern look…I have worn it all my life. Which clothing item make the leap…quality fabric and good design,,,,not too much of any one thing. If there is fringe…a minimal amount of high quality suede…more subtle versions of the trend. Shoulder pads have always been around to help define or triangulate the torso creating a point-like waistline. The trend that expanded them was awful and is so dated. A very slight padding for well cut suit jackets is great.

 I just keep seeing certain trends return again and again. There may be subtle changes to make an earlier trend outdated……yet some of the older versions can still hold their luster. It must be the design and/or simplicity of the garments lines. It could also have something to do with the quality of the materials, or the the garment is really comfortable and functional ( ballet flats, slacks on women, caftans) One thing I have noticed in the pieces that held up…they lacked excessive details and where well designed and well made of high quality material–they were also expensive.

Artisan pieces hold up well as they are not always “on trend” What I purchased decades ago was not on trend at all. I really did not know about trends, but loved rich materials. The only items I had problems with were those with very large shoulder pads, but that was later after the really great pieces were purchased. I still have several of them. That is all I can really communicate as it is an intuitive sense when I see it I KNOW it.

It is interesting how a few years changes everything.  I still have many dresses, blouses, jackets and such purchased in 1987. The big shoulder pad trend….B-I-G man size rectangle jackets with these football (American football) shoulder pads propping them up.  

So, I have hung on to this most incredible blouse,  a couple of jackets and a dress.  I know I will never wear them again.  So, what makes them look so dated as I was never into the shoulder pad trend and purchased the most minimal of shoulder padded clothing—which was all I really had to choose from as this trend went biserk when the Dynasty sitcom hit t.v. screens.  It was also a time when women were breaking the glass ceilings in the corporate world and floundered a bit with style trying to “Man up”.

 So, I looked at this one particular blouse from that period.  Oddly, it was not the shoulder pads (mine were so minimal I could not really tell), but the cut of the sleeve into the shoulder.  They were puff 19th century sleeves that made me look like I was some member of a cult.  Also, the bat wings sleeves on top of the puff sleeve shoulder inset, on top of the little shoulder pads.   I really love bat wing sleeves and cocoon shapes.  Cocoon shapes remind me of the twenties a bit…my favorite time period.  I also love bat wings.  However, the 1980’s trend seemed to combine all three into an utter disaster…and I own the proof.

 Unfortunately, this blouse is the most gorgeous shade of slate blue/grey and really enhances the color of my eyes like nothing I have ever owned before.  It is also made from the richest most beautiful silk.  I know that is why i bought it.  It comes in at the waist with gorgeous pleating and little dressmaker details….but those sleeves and shoulders ruin it.  The good news is that there is a scarf attached to this blouse.  I am thinking of having the scarf removed by the tailor if possible. I will still have a piece of my history

 LESSON LEARNED:  No matter how high the quality of fabric or gorgeous color, if it has too many trends of a time period combined….it’s has a short shelf life. 

 I like bat wings with more kimono or drop shoulder styling.   I will never by puffed up sleeves at the shoulder.  Shoulder pads must be so minimal as to be almost invisible.  Some fabrics  benefit from a little ..very little shoulder shaping. 

You can also find Lisa at Following Frida

 7 Elements of Timeless Clothes

If you want to find some pieces that will be more timeless and have longevity in your wardrobe, here are my top tips to look for based on my experience and going through lots of wardrobes!

1. Great quality fabrics – but natural fibres such as fine wool, cashmere, silk and suedeWhich clothes date and which clothes are more timeless and will last longer in your wardrobe?


Next: garment constuction


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I'm not sure if it's for you but how would you feel if you learned all about the colours and styles of clothing that suit your individual personality, shape and style? Just imagine what it would be like when you can open your wardrobe and pull together fabulous outfits that make you look and feel amazing every day? If you'd like to stop wasting money on the wrong clothes and accessories plus join an amazing bunch of very special women also on their style journey - then my 7 Steps to Style program is right for you. Find out more here.

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  • Great job with this thought provoking topic. I think you nailed it and really made some comparisons that were accurate between what items of clothing will date vs. those that will transcend time. I am wondering about kimono styled tops and jackets. Kimonos have been around for centuries. I purchased them before they became a trend. A year or so ago kimonos became a hot trend. Of course, I saw it as an opportunity to try some new colors, lengths, and styles. I wonder when the trend passes if it will return to its previous status where new offerings are few and far between. Previous to the trend, I thought they fell into the “artsy” group. “Arsty” clothing…usually offered in small boutiques or art events fall outside of trends and can gain a luster about them if they are somewhat mainstream. I would love to hear peoples thoughts on this post and various topics/questions it raises.

  • One comment I would also like to add is that some color trends are most welcome…navy and grey were on trend a few years back. Certain greens, burgundies, purples, plum, and certain reds can be on trend for a season and if the color suited me, I made investments in a few classic pieces. So, it all depends on what color is on trend that year. I did not purchase a single item of clothing during the neon trend…well an tee shirt for running in the dark…that does not count.

    • I completely agree with you, and I suppose most of us who live in regions that experience distinct seasons do this intuitively. A number of years ago, though, I came across a style of dress in medieval Japan that very distinctly echoes the seasons and influenced the way I dress now. Basically, kimono were worn in multiple layers of prescribed colors to imitate the natural world around you. (Look up junihitoe on Wikipedia if you want more information.). It occurred to me that I dress seasonally as well. I live in Pennsylvania, and my oranges and browns are rarely touched after Thanksgiving. In fact, fall is the only time I will wear orange. It is simply not my color, but in the fall, burnt orange is something I can “get away with.”

      Once I started to think that way, it really influenced the way I shop. My two- year-old kelly green blazer is already out of fashion, color-wise, but every year it will be in fashion during the Christmas season and around St. Patrick’s day. Brighter reds come and go, but they are always appropriate around Christmas, Valentine’s day, and patriotic holidays here. Similarly, if I see an expensive piece in a natural color for its season, I will snatch it up without hesitation. By that logic, I will pay more for warm weather clothes in spring and summer colors and cold weather clothes in fall and winter colors. I won’t spend much money on a pastel sweater, though, unless it’s a silvery or icy color that will always be remeniscent of the snow.. Why fall in love with something you’ll stop wearing after a couple of years?

      It’s fall here, so I will happily buy browns, burgundies, deep purples, darker greens, and burnt oranges to last, knowing not only that I will wear them every year for a few months, but also that I will mix them in a more adventurous way because that reflects nature in the fall here. (I’m generally pretty conservative with my use of color.). Once December begins, I will ease out of the browns and oranges and wear some brighter reds and greens, plus some “frosty” winter colors if the weather is colder the snows start early.

      The other big benefit to this idea is that, if your basic palette changes every 2-3 months, you don’t get bored with your wardrobe as easily. I really don’t own a lot of clothing, but playing the colors off each other seasonally and adding lower priced on-trend accessories helps to make my wardrobe feel much more extensive than it actually is. (And thank you, Imogen, for beating into my head that any color trend that matches my own coloring is worth an investment piece as well!)

  • Lisa and Imogen, a timely article. I have several wardrobe items from my mother who bought quality pieces. As you mentioned, colors are cyclical in clothing as well as in home decor. I say to wear the colors which are the most flattering to you regardless of the year’s trendy ones. If a committee meets to choose that year’s color, beware! Well fitting clothes always look best. Some designers seem to enjoy making women look ridiculous—avoid them! An objective analysis of body proportions is very useful in choosing styles that enhance one’s assets and mask one’s less desirable areas. Imogen has done countless posts about the importance of proportions in prints, body types, shoe types, etc. As you said, Lisa, classics are a good investment!

  • Wool. I have two hand-knitted jerseys from the op-shop that transcend fashion…I think. Before you run barfing from the room – they’re in neutral colours, one grey and one deep blue-green, and the level of knitting skill is way up there. The yarns are nice. They’re both shaped to fit the bod. They make sense, they’re warm, they fit, and they’re beautiful pieces of craftwork in their own right.

  • I really enjoyed your insights on how to look at clothes! I don’t think I have ever been a fashion devotee with most of my everyday clothes being pretty boring, tees and jeans. The few pieces that never get culled from my wardrobe are probably within the creative or ethnic category and never were “in fashion” at the time. My color blocked shoes are too much fun to ever give up and will stay but I never got into the color block look as a whole since I “blend” my colors. I will always love peplums and peplum jackets and handkerchief hems. I think I stopped caring about what was “new” unless I really liked it and I think that is how you should approach your wardrobe: take what you want from fashion and what you choose forms your style.

  • Very interesting article and comments. When I think of timeless fashions I think of a classic suit coat, well cut from wool or cashmere. A good trench coat is another article of clothing that always seems in style. I think that blouses, tops and dresses can be trendier, they usually are replaced more frequently. I love the pictures of clothes from the 1940s. I look at pictures of my Mom in peplum jackets and she looked very stylish.

    • As a former owner of a vintage shop and designer myself, Lisa has asked me to weigh in with my opinions on this subject so here goes. Great insight from both Imogen and Lisa on the topic. Fashion is of the times and it reflects the culture, economics, technology, innovations and zeitgeist of what is happening in the world. In the past fashion, as with society has been homogenous, as in everyone has a similar lifestyle, set of beliefs and place in the world meaning that fashion was also set, adopted and followed rigorously. Take hem lines as an example! In the past a hemline was set at a particular length and that was it, everyone wore theirs at that length. These days the world is diverse and pluralistic and so is fashion. There is no absolute fashion style dictated for everyone, rather a series of trends aimed at turning over a multi billion dollar industry. Therefore fashion has become eclectic and varied, you really can wear a multitude of styles. When it comes to wearing pieces from yesteryear there are a number of appproaches. One can incorporate a piece into your everyday wardrobe, this relies on it suiting you, your body shape, colouring and other pieces you have. It may or may not be timeless having obvious signifiers of that era. It will contribute to your unique style. Vintage us considered to be a trend in itself. Or, you can also embrace a whole vintage look, even though it is not currently in fashion. Or you can relate a piece to a current trend. Some current trends are Graphic which refers back to the geometric and primary fashions of the 80s. Pieces that are black and white check, chevron patterned or primary colours are again current. If you wear the look head to toe it may look like a costume, refer 50s style pin up girls that include hair and make up. So if you want to avoid this, then keep hair and make up contemporary. The 80s is technically not yet vintage. In another 5 to 10 years it will be. Younger generations are already embracing its revival. For 18 to 25 year old it is an extreme novelty and they are hot for it, as I was when I was the same age in the 80s. It does look great on them too! There is the old saying that if you have worn it the first time around, don’t wear if for the second time as it will look dated. The fact that maxis are peplums are currently being produced attests to the idea that there are no new ideas, just new fabrics and good marketing. Personally I am excited about the influence of technology on fashion and cannot wait to see garments made with 3d printing entering the mainstream. It is great to see what has come behind and I collect treasure may garments from yesterday myself. I only tend to wear what suits me though so tend to embrace waisted 1950 s looks to early 1960s. Because tribal and ethnic is a current trend (with new garments bring produced in this style) there is wholesale acceptance of maxis and kimono’s. People are well travelled do the influence of other cultures has seen fashion and interiors respond to other ethnicities in a broad way incorporating them into western style clothing.

  • Jacket collars keep looking dated every decade to so. I’m a petite gal with broad shoulders, so mandarin collars suit me, and they never seem to get dated.

    I’ve also started converting some of my button-downs with regular collars into mandarin collars using this tip: http://www.instructables.com/id/Change-a-Shirt-collar-into-a-Mandarin-Collar-with-/

    Skirt lengths. I like longer skirts, but stick to streamlined pencil silhouettes. Flares and flounces date more easily.

    The flares on pant legs. Since I’m a petite 8 shape, I don’t have a choice. I stick to slim pants and they never fail me.No matter what the trend, I take the pant to the seamstress and get it shaped to a slim cut.

    • OMG. I’m short and broad-shouldered myself, and I love mandarin collars. I’m always cutting up clothes (I have some cute satin dressy shells for with suits that started life with flutter sleeves on – French seams meant those sleeves came right off with a clean edge) and yet somehow I never thought of converting regular collars to mandarins like this! I know I’m a month late here, but THANK YOU. You just made my fashion day.

  • I think when a look is extraordinarily flattering, the look is timeless for that particular person.

    For example; 1) cowl necks and long, fitted turtle (polo) necks are timeless on those with long, elegant swan necks; 2) true hip-hugger (as opposed merely low-waisted) pants are timeless on shortwaisted women with extremely narrow pelvises; 3) horizontally striped tops are timeless on longwaisted women who are pear or triangle shaped; 4) 3/4 length sleeves are timeless on women with long arms; 5) boat necks are timeless on women with long necks, narrow shoulders and perfect posture; 6) belted cardigans and jackets are timeless on x-shaped women; 7) above the knee skirts and Bermuda shorts are timeless on those with perfect knees 8) and even high-waisted, pleated trousers look timeless on the .000000001 percent of the population who is tall, thin, long and thin waisted with a stomach that doesn’t protrude one iota.

    • Well said Monica.

      Boat, cowl, mandarin and V necklines, three quarter sleeves, tunics and classic linen shirts, wrap/sarong and shirt-maker dresses, pencil and below the knee skirts, gaucho and straight linen pants, have been in my wardrobe for many decades will be for decades to come.

      I found my style years ago and I patiently wait till the trend catches up with me, again and yet again.

      I look back at old photos of me and have had no real reason to cringe…

  • Interesting question. I like looking at women in shopping malls and guessing their ages from what they wear as each decade seems to have a different silhouette. One exception was an elderly lady in an of-the-moment kaftan top. Then her daughter appeared in a similar top and I could guess who helped who with shopping!

  • Great article and comments!
    I struggled between buying timeless items and trends for years. I am definitely drawn to the classics, but found that dressing classic head-to-toe can be aging and sometimes boring. I try to wear one trendy element per outfit to balance the look. The element can be hair, accessory, skirt length, etc.

  • I do quite agree with Imogen. I find that both fabric and cut are equally important when it comes to a timeless piece. I do know this from experience too —- I have a few neutral colored pencil dresses in rich fabrics that are over 5 years old but still look perfect. However, patterned pencil dresses in more ‘stretchy’ and cheap fabrics already look dated, though they are just a couple of seasons old.

    Apart from pencil dresses and skirts, I also think that fit and flare styles are quite timeless when chosen correctly. Neutral colors in structured fabrics and no detailing apart from the perfect lines of the neckline n hemline also are timeless. I don’t think I can say that about anything with too much flounce or flare though.

    I find structured peplum tops also never date when picked in neutral colors and structured fabrics (not stretchy materials that cling ).

    Imogen has most coats and jackets covered. I also believe that a classic cut leather jacket that nips in at the waist (not boxy) and has no metallic detailing on pockets and shoulders should stay timeless. I do have a deep brown leather jacket and I wear it very often. I think tan and black might have the same effect. If you’re going to spend money on a leather jacket, stay away from bright colors that scream ‘fake’. Those will date easily, no matter how expensive.

  • You make great points about acquiring timeless pieces. Classic cuts with small patterns and quality fabrics typically are included in timeless pieces, just as you shared.

  • All great comnents! But i just buy what i like and feel comfortable in. But a little lace on any item is timeless. Lace has been around forever! So when i shop i always seem to go for anything with a little or a lot of lace. I wore a top out that i have had for about 7 years it has a longer lace overlay over a simple cami style top. The comments i got were unbelievable!! Ladies wanting to know where i bought it. Im also a little bit boho.. lots of colors and loose clothing. I dont think things like this will ever date. I love comfort!!

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