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We all love comfort. And leggings are very comfortable. And they are back again. Read how not to style them to avoid look old fashioned or like trying too hard.

  1. Leggings in the 1980s
  2. Avoid These Styling Mistakes When Wearing Leggings over 50
  3. To Wear or Not to Wear Leggings in Midlife
  4. Muted or Dark Color Leggings Are Most Flattering
  5. Get the Proportions Right When Wearing Leggings
  6. Structure or Knit Pattern on Leggings “Add” Pounds
  7. Leggings the Modern Way
  8. Posh, Chic and Modern: Leggings with a Long T-shirt
  9. What I Wore on Sunday


Leggings in the 1980s

In fashion everything old gets new again. You have heard that before, and in fashion over 40, we have seen some chic perennial or decadal trends. In the Eighties, leggings were a big thing. We wore them with the long blazers that were hip back then. We also paired our leggings with long sweaters that had these awkward shoulder pads. We styled the leggings with court pumps with a 2 inch (5 cm) heels. Jewelry-wise, we accessorized our leggings with oversize hoops when we wore the leggings with a blazer. We added studs plus a big statement necklace when wearing our leggings with a long sweater. We went for posh, chic, and professional on Casual Fridays, well as professional as one can be in leggings. 😉

In the aftermath, everything was oversize including the hair volume on the sides and/or on top of our heads. Recall those antenna bangs? I loved them, actually I still do. Even though Charla Krupp the author of How not to look old suggests to cut bangs to look younger. I meanwhile think that bangs only look great when you come from the hairdresser. A week or two later you have to go back to regain the great look.

Avoid These Styling Mistakes When Wearing Leggings over 50

Back to the leggings. Now leggings are having a moment – again. Don’t make the mistake to even try to style your leggings the way you did in the Eighties. For one, this time around there are no mid-tight long blazers. Second, leggings are not pants. Thus, they are not meant to be worn with anything that does not cover the bum entirely except at the gym. 😉 And even there, styling them in Bombshell sexy way is the way to go. And that’s not necessarily a look a you want to go for when you want to work out.

midlife blogger in chic sequin skirt
Sequin skirt with Jeanne Pierre striped sweater, statement belt, Levis denim jacket, GNW tight, Vince Camuto slouchy boots (all own) and pearl necklace c/o The Pearl Source Inc.


Last time around, only leggings for the gym had prints. These leggings were made from some sort of lycra. This time around, non-lycra leggings have all kinds of prints and pattern including skulls, ikat, zigzag, horizontal stripes and florals. … and designer leggings are printed on demand.

Don’t go for horizontal stripes. Here is why: Any horizontal lines visually broaden. This means your legs look wider than they actually are. Even worse, everything horizontal also visually shortens. Unless you have legs as long as Vivian Ward in Pretty Woman, you most likely don’t want your legs to look shorter than they are. Overall, these horizontal pattern add pounds. Period.


influencer in Redbubble print-on-demand sunflower leggings
Print-on-demand sunflower print leggings c/o Redbubble with own T-shirt and ballroom dance shoes


If you go for a printed pair, avoid colors that are from all places of the color wheel. Leggings with a print in one color family are easier to style and pull off than overly colorful print leggings. The sunflower leggings shown in the styling examples work because the sunflowers are not brown plus green plus yellow, but in shades of an old black and white photo. These colors make the print look posh and chic even for women in midlife. Abstract prints are great on fishing apparel for outdoor activities.

Daring sequin leggings – think twice before you fork over the money

There are these sequin leggings. They are awesome. I love them <3 . Thus, I tried a black pair out. Big mistake! I rejected them immediately after I saw my reflection in the mirror. The sequins looked cheap giving me a trashy look. If you want to pull them off, make sure the sequins don’t look cheap. Moreover, wear them under a tight-long white oxford shirt or a leather dress with sandals for going out for dancing. Be aware that anything shiny visually adds pounds. There is hardly any other material that is as shiny as high quality sequins. Dark colors like black add less than gold, which adds less than silver. All other colors are kitschy. More on how to look ageless in sparkle.

To Wear or Not to Wear Leggings in Midlife

Can you wear leggings over 50? Ask yourself whether your legs are your favorite body feature and whether you want them to be in the center of focus. If the answers are yes to both questions, try them on. Take selfies from all sides, ask a salesperson how many of them are available in your size. If the pair you tried on is the only pair left, ask them whether they can hold it for you for 24 hours. If you still love how you look in them after a night’s sleep when looking at the selfies, ask yourself whether the prize is worth the fun and what the cost per wear will be. If you are still ok with them, by all means go get them.

In all other cases, skip this trend and save the money.

Muted or Dark Color Leggings Are Most Flattering

Speaking of color again. Do I have to mention that only storks and flamingos look great in fire-engine red legs, sand-hill cranes with bright yellow legs, ducks with Halloween orange legs? While a young woman gets forgiveness for legs in the color of crayons or even neon, we 40+know better that legwear in these colors are never a great style even at the gym. They are just cute on little girls. Go for muted or dark colors. Recall that dark colors have a visually slimming effect, i.e. avoid to go for a light colors when your legs are on the heavy side. Dressy twill leggings can even be  styled office appropriate on Casual Friday. For long road trips a long slightly oversize sweater with a pair of dark wash  jeggings make a comfortable, but stylish look.

Get the Proportions Right When Wearing Leggings

Be aware of the proportions. You certainly have heard to never pair something tight with something tight, or something slouchy with something slouchy. The first is a recipe to look trashy and cheap, the second to look frumpy. Both looks are not the style you are after. Thus, always pair your leggings with a top that is not tight.

However, don’t overdo it. The volume must stay in proportion. If you are pear or apple shaped with very slim legs you may end up looking top-heavy. Therefore, don’t make the mistake to not have a top with you that you plan to wear with the leggings. Again take selfies from all sides to check the balance. If you like what you see, get the leggings.

Structure or Knit Pattern on Leggings “Add” Pounds

There are also these leggings that have a knit structure. It is obvious that any structure adds pounds. These leggings need long lean legs. My main reasons to reject these coarse knit leggings is that the knit has a lot of see-thru, which is not a great style. These gaps caused by the loops of the knit are also a recipe for catching a cold when living in a climate where temperatures drop below freezing in winter. More on cold gaps.

Leggings the Modern Way

You can wear the leggings with a long cable-knit sweater and wool socks in the same or similar color like the sweater. Think of Annette Benning as Sydney Ellen Weight when watching TV with President Shepard at Camp David. It is a very classic weekend look. The shoulders should have no pads. No jewelry except some diamond or pearl studs – fake or not, it doesn’t matter.


over 50 years old woman in leggings with chic cable-knit dress
Sunflower print leggings c/o Redbubble with own Barbour cable-knit dress, pointy toe pumps and various strands of pearl necklaces with uppermost c/o The Pearl Source

Posh, Chic and Modern: Leggings with a Long T-shirt

Another modern way to style leggings is to pair them with a long T-shirt under an open trench coat, again for a weekend look. Add pointy toe ballet flats, a long pendant necklace and a saddle bag or satchel. This look works best in neutrals with a pop of color. Adding the pop of color is the easiest with the bag or shoes. The photo above shows an example wearing leggings under a cable-knit dress. The look is finished with pearls and pointy high heel toe pumps, read higher than the 2.5 inch (5 cm) of the Eighties.

Pro tip: Be aware that the point where your top (sweater, dress, tunic) ends automatically has a horizontal line. Ask yourself whether you want to draw attention to that part of the leg. If the answer is no, that top leggings combination is a mistake. Don’t wear it.

You can find more on how to look stunning in athleisure in the guide at the link.

Do you have already a pair of leggings? If so, how do you style them? If not, are you planning to jump on the leggings band wagon? Did you wear the look back in the Eighties? Do you like the look? Did you like the trend back then? Let me know by sending me an email.

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What I Wore on Sunday

Now to the OOTD. It shows how to wear sequins in a casual way for staying warm. I wore this look for Sunday brunch.

over 50 years old women in sequin skirt and denim jacket
Side view of casual outfit with sequin skirt with Jeanne Pierre striped sweater, Levis denim jacket, GNW tight, Vince Camuto slouchy boots (all own) and pearl necklace c/o The Pearl Source Inc.


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Photos: G. Kramm

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