3 Ways of How To Style a Midi Dress Casually

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As older women, we tend to think of dresses as something to wear for fancy. Yet in this day and age, dresses can be just as casual as a pair of jeans.
That’s why I was excited to have my friends join forces in how to style a midi dress casually. Laura and I are wearing what I usually call a “midi” dress, and Gurmeet is styling a knee-length dress. Yet you could use Gurmeet’s ideas for a longer dress too.
However, don’t get stuck on the terms. When I search for a midi dress, many dresses at the knee length show up. It all depends on our perspective.

Quote of the day: “If you need 10 of something, make 30. Then pick the best.” Rick Rubin

The quote really made me stop and think. Because especially in our outfit planning, things don’t always come out the way we imagine. But that doesn’t mean the idea is wrong, or we are bad.
They are just clothes, and sometimes, certain combinations look better than others.

That’s why I love trying to give multiple options of how to style a midi dress casually. One of our looks may give you the inspiration to find similar items in your closet and create a whole new look to you.

Definition of Midi Dresses

For us older women, the midi dress used to be called a tea-length dress. It’s the length in-between the mini and maxi styles. Which means it could be very different from woman to woman. In fact, I’ve seen them called midi dresses that range from the knees to the ankles.

The advantage of this length of dress is they are usually easier to sit down in. You don’t have to worry about someone seeing up your dress.
It’s even better if the midi dress is the tiered style or has an a-line skirt because then it’s very roomy too.

Many women complain about this length of skirt cutting them off at mid-calf and making them look shorter. I say hogwash to that thinking. There is no time I have ever looked at a woman wearing a midi skirt/dress and had that thought. It’s pure brainwashing from articles you’ve read.
So wear the midi skirts and enjoy these ways how to style a midi dress casually without worrying about that factor.

I’ve written other articles about this length of skirts and I hope you give those a gander for inspiration too.

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Laura: How to Style a Midi Dress Casually with Ankle Boots

Dress: Velvet Heart from Naomi & Ruth~~Wrap Top: Forevere 21~~ Boots: Dolce Vita ~~ Bracelets: SG Sparkle~ Earrings: Everwild ~~ Purse: no label-from Naomi & Ruth

Laura is my forensic scientist friend who turned into a non-toxic soap/skincare maker. Her company is called Scrub Studio and with my code, JODIE10, you can get 10% off. You never realize all of the science that goes into making these products, and Laura is truly skilled because of her background.

For her idea of how to style a midi dress casually, she opted for a knit wrap topper and ankle boots.

What I really love about Laura’s outfit is the unexpected color combination. Light blue and olive green create a wonderful contrast. In fact, if you think about light blue like you do a light wash of denim, then you may never wonder what goes with it again. Because, like denim, the answer is everything.

This knit wrap top is the perfect topper for this tiered midi dress because it’s shorter and thus doesn’t interfere with the tiers.

If you thought that tiered dresses were going to peter out after last year, you’d be wrong. You may still be reminded of Little House on the Prairie, but I think once you try them, you’ll realize how comfortable they are. Besides, they are very modern right now, and it’s good to look like you live in this time period.


Let’s talk about the fabulous extras in this look. First off the earrings and bracelets. The bracelets are sold by Gurmeet’s store on Etsy, SG Sparkles. I love how they bring in some extra color of green/turquoise just like the earrings do too.
My motto is always the more color the better, and I love how Laura is doing that, yet in a small way.

The quilted crossbody purse also is a factor in how to style a midi dress casually, because it seems the opposite of dressy.

My favorite part of the outfit is these ankle boots. Just look at that sparkle.

Insider tip: If you worry about too much sparkle on your clothes, then incorporate it into your footwear instead.

Jodie: Layer a Sheer Top Over a Midi Dress

Dress: Velvet Heart from Naomi & Ruth~~Top: Zara ~~ Shoes: Adidas-Goodwill~~ Belt: Amazon here ~~ Head Scarf: Gibby’s-no longer available~~ Earrings: Lil Shop of Ours~~ Purse: no label-Bealls

So I created the same proportion as Laura with a top layer that ends at the waist. That’s not to say that’s the only way to layer. In fact, Gurmeet shows how to layer with a longer item below.

I decided to wear a sheer top over my tiered midi dress. You may remember this dress from our trip to Puerto Rico. I wore it when walking on the beach with a kimono over it for sun protection.
Yet just because the dress is perfect for a tropical vacation doesn’t mean I can’t wear it around Phoenix too.

For those of you that don’t appreciate a tier starting at your hip area, there are many of these midi dresses that are straight around the hips like the one I am wearing. If you would like more options, just let me know.

When you use the trick of wearing a shirt over a dress, there is that issue of what to do where the shirt ends and the dress begins. If your shirt is the right length, you can just leave it be.
But if you need to shorten the shirt, then adding a belt can be one solution.

I recently found this belt on Amazon. If you haven’t embraced the wide elastic belts, this is your sign to try one. It comes in a couple of different colors and sizes up to a XXXL. (I would size up one size.)


Even though my sheer top is orange, I thought I would accessorize it with bright pink. The combination of orange and pink is such a happy pairing.

The earrings are from this company called Lil Shop of Ours on Instagram. They are two sisters who handmake these earrings (and pendants) and can customize them with whatever colors you want.

I thought the white tennis sneakers were a perfect option for how to style a midi dress casually. These kinds of sneakers are very, very popular right now.
I’ve found some for you below, or your best bet is DSW or Zappos.

GurmeetWearing a Vest Over Her Dress

Dress: ~~ Vest: ~~ Boots: Necklace: ~~ Bracelet: ~~ Earrings:

I was actually at Naomi & Ruth Boutique when Gurmeet bought this dress. She wasn’t sure exactly how to style it and was worried it was too form-fitting. Of course, I tried to allay those fears and even created a video with a similar dress I own.

Even if Gurmeet’s dress was longer like Laura’s and mine, I think this vest would be amazing with it. It would still have the proportions of being 2/3 of the look, and the skirt of the dress only being 1/3.

I was swooning over this vest and I just love how Gurmeet tied the self-belt to hold the vest in place. It creates a beautiful waistline and looks terrific.

Another great element is the tall boots. Tall boots are essential in cooler weather to make a dress comfortable for the winter, and they can also be a factor in how to style a midi dress casually.


Gurmeet is the woman behind SG Sparkles on Etsy. She gets some of the bigger Indian jewelry from her source in India, and then she has been creating her own pieces too. In fact, she even makes collar charms for your pets.

Many of her necklaces even come with matching earrings, and the pieces are just fabulous.

You don’t see Gurmeet’s purse because she’s not a purse person. She would rather have pockets and use those instead. However, you can see in the candid photo at the bottom of this article, she does have a beautiful bag in her hands.

You can also see that both Gurmeet and I donned a coat in the top and bottom photos. It was a chilly day when we took these photos.

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Photo credit: Rob Filogomo

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