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How to Wear a Hi-Low Skirt Without Looking Stuck in the 2000s

Fashion trends always come back around, but sometimes they need a little updating to feel modern and wearable. That’s exactly how I feel about the hi-low hemline.
Our Thrifty 6 group’s prompt was hemlines, so I figured it would be fun to have my crew explore how to wear a hi-low skirt.

Quote of the day: You don’t get what you wish for. You get what you work for.” Unknown

The best part is that hi-low pieces already do a lot of the styling work for you. The asymmetrical hem creates interest, drama, and shape without needing complicated layering tricks.

For this outfit challenge, the three of us all interpreted the hi-low idea differently, which proves there’s no one “right” way to wear it.

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Jodie: DIY Drama with Layers

You may not NEED complicated layering tricks, but I wanted to show one. Leave it to me to show that I can’t wear something “as is.”

I had seen a similar skirt on an influencer and couldn’t get it out of my head. SO when Untuckit gifted me this skirt, I decided this one would be the one to DIY.

I cut the 2 lower tiers off in the front to make it open.

Stylist trick: I actually kept the second tier and placed hooks and eyes on it, so I could make the front part longer at times.
In the winter, I like it short when I wear it with tights. But if I want to wear it by itself, I’ll add the second tier.
Today, I layered a gold skirt (seen styled here) under it.

Details:

-Valerie gifted me this purse that was created out of 3 different men’s ties. It also came with a matching clip that I used in my hair (check out the photo from the rear).
-Who knew I’d be wearing a tube top in my 60’s, but I Love the bit of sequins showing at the vest neckline.

Charlotte: Handmade Plaid with Personality

Charlotte’s handmade plaid skirt proves that a hi-low hem can absolutely work for everyday wear.

Her version is a pastel plaid print hi-low skirt she made years ago. While your traditional plaid seems classic, this one adds spunk and personality.

My mom has worn the skirt with a pink top and with a blue top in the past.

Details:

-Notice the flower pin at the waist…my mom made that with leftover material from the skirt and then just pinned it on a pink scarf she was using as a belt.
-The lace blouse is tunic length and made to be a swim cover-up. But I love how Mom layered it over the yellow tank top and tucked it into her skirt.

Valerie: A Hi-Low Dress with Fun Accessories

Valerie took a completely different approach by wearing her hi-low skirt as part of a dress.

The dress itself already has movement, so the accessories become the “personality” pieces.

Stylist tip: Accessories can change up the vibe of your look and add color easily.

Details:

-Valerie wore this dress open as a vest when we talked about fringe earlier this year.
-Let’s talk about how Valerie was the boss of her items today. Not only is she wearing a belt as a necklace, but she also decorated the necklace AND the purse with bow barettes (made for your hair, but they work in other places too)

Why Hi-Low Hemlines Work at Any Age

One of the reasons I still enjoy hi-low styles is that they solve common outfit frustrations.

They can:

  • Add movement to stiff fabrics
  • Create a shape without tightness
  • Show off shoes
  • Make skirts easier to walk or climb stairs in

And unlike bodycon silhouettes, hi-low hems don’t rely on having a certain body type. The shape itself creates visual interest.

That’s why the three of us can wear the same concept differently and still make it work.

Ideas For How To Wear A Hi-Low Skirt

The Secret to Modernizing a Hi-Low Skirt

If you’re wondering how to keep a hi-low skirt from feeling dated, here’s what I’d suggest:

1-Choose modern fabrics

For example, in the summer, concentrate on the natural fibers and look for prints that catch your eye.

2-Mix in unexpected elements

This is my favorite idea with dichotomy.
You could add sneakers because that’s a casual element with a skirt, or mix your prints. Think of something unlike your norm.

3-Avoid overly matchy styling

The more perfect everything looks, the more costume-like it can feel. A little contrast adds personality.

4-Focus on movement

Hi-low pieces are meant to move. Lean into that energy as much as you can.

Options For How To Wear A Hi-Low Skirt

Final Thoughts About How to Wear a Hi-Low Skirt

I think we have succeeded in proving that there are endless ways to wear a hi-low skirt.

The secret is in making it feel like you.

Because at the end of the day, style gets much more interesting when we stop asking, “Is this trending?” or “Does this make my butt look big?” and start asking, “Does this feel fun?”

How To Wear A Hi-Low Skirt Without Looking Stuck In The 2000S &Raquo; Befunky Collage

Thrifty 6

Because the fashion and textile industry can be a major contributor to landfills and other environmental pollution, we decided that the mission of this group is to focus on second-hand items.

Thrifty tip: Don’t forget to check out the men’s and kids’ sections of the store because you might be surprised.

Check out the other members of the Thrifty 6 group below for how to

How To Wear A Hi-Low Skirt Without Looking Stuck In The 2000S &Raquo; Shelbee T6 Hemlines

Shelbee of Shelbee on the Edge

“I had no idea how to approach this hemline theme so I decided to see how many different hemlines I could combine into one outfit. From the bottom up: Layer 1 is a yellow lace super maxi dress. Layer 2 is the maxi dress I wore for last month’s Belt It theme. Layer 3 is the patchwork midi skirt I wore for our Crochet Revival theme. Layer 4 is a Kantha Bae apron/smock/tunic/dress thingie. I topped those 4 layers with a yellow paisley kimono tied at the waist, a hip length patchwork print coat, and a floral scarf. Other than my hat, everything was preloved including my jewelry and moccasins. I was really pleased with this look but there are A LOT of layers to contend with!”

How To Wear A Hi-Low Skirt Without Looking Stuck In The 2000S &Raquo; Tweed Skirt With Black Otk Boots 1

Nancy of Nancy’s Fashion Style

I bought this skirt twice. The first time was when I had just started working in the fashion store, in 2007. We sold a lot of skirts like this. With ruffles and petticoats. All just a little bit different from the norm. And super feminine. The second time was sometime in 2019 via Vinted. Because I thought the skirt was amazing back then. The second time wasn’t. The length didn’t suit me anymore and this style didn’t fit me anymore. But it was beautiful, and tweed! Which is a plus!

How To Wear A Hi-Low Skirt Without Looking Stuck In The 2000S &Raquo; Cjm Hemline Shimmy 1

Jane of Preloved-Vintage-Handmade

“I totally fell for this Japanese inspired dress, adorned with golden flowers – shame it was too tight and too short, but I don’t let stuff like that bother me…
I’ve replaced the back zip with a fantastically chunky and oversized statement zipper that runs the entire length of the dress. Now the zip’s a feature to be exposed allowing for two extra inches of width – enough to fit me perfectly plus a bit of shimmy space.
To add length, I’ve attached a pleated trim to the hemline – it’s giving Issey Miyake Pleats Please vibes so totally in-keeping with the Japanese aesthetic – I loved it so much I added some to the cuffs too…
With these simple alterations, this dress is party-perfect and I’m doing a little hemline shimmy for Sally from T6 – Sally chose ‘Hemlines’ as our theme for May – such a fun theme!”

How To Wear A Hi-Low Skirt Without Looking Stuck In The 2000S &Raquo; T6 Hemlines Sally In St Paul May 2026

Sally of Within a World of My Own

“I celebrated an unusual hemline by styling a black-and-white outfit around this thrifted knit skirt: it has a hi-low hemline that I don’t care for so I always wear it sideways to create a diagonal hemline instead.  I topped off a black column with a thrifted check shirt and thrifted polka dot scarf for some easy print mixing. I finished my look with handmade beaded bracelets and necklace for a simple, fun, and comfortable summer outfit. I am a real color lover, but I thought the mix of geometric prints and multiple textures with the asymmetric hemline kept this achromatic look interesting.”

How To Wear A Hi-Low Skirt Without Looking Stuck In The 2000S &Raquo; Emma T6 May

Emma of Style Splash

“I was completely stumped as to how to approach this theme; my immediate thought was asymmetric hemlines, but I couldn’t think of anything preloved that fit that criteria. Then I remembered this Iris Apfel x H&M skirt that I bought on Vinted a few years ago. It’s a heavy layered maxi, that looks and feels like two skirts. A while after I bought it, I managed to find the blouse in the same print too…you know I love a matching set!

Online Thrift Stores

If you don’t have great secondhand stores near you, then another great option is online thrifting. These are the ones I’ve used.
thredUp
Poshmark — here is the post about how to shop the site.
Etsy
ebay
The Real Real— higher-end and designer brands, but some are priced affordably.

Creating Outfits For How To Wear A Hi-Low Skirt

Photo credit: Rob Filogomo

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Layering Necklaces With Sequins And Vest

Jodie Filogomo is a retired cosmetic dentist and fashion blogger behind Jodie’s Touch of Style, where she has been helping women over 50 experiment with style in fun, creative ways for over 12 years.

Find out more about the crew, because we love to showcase all ages, body shapes, and women who love different styles.

The post How to Wear a Hi-Low Skirt Without Looking Stuck in the 2000s appeared first on Jodie’s Touch of Style.

Jodie's Touch of Style showcases how it's never too late to look great including other older women and myself talking about fashion, beauty, and lifestyle issues.

As a retired dentist, Jodie takes her love of clothing and shopping and has come to find her superpowers in styling the same item in many ways. She is also a huge advocate for embracing our age and bodies. Getting old is a wonderful thing and learning to love ourselves while it happens is very freeing.

Looking great can happen no matter what age, shape or budget, as we show on Jodie's Touch of Style.

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