Grown women wearing midi skirts and boots

Stylish Opportunities of How to Style Midi Skirts and Boots

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I think winter is the perfect opportunity to wear midi skirts and boots. The options to keep you warm lie in the layering aspects plus I’m going to give you a ton of reasons to embrace skirts below. Believe me when I say you can be just as warm in midi skirts and boots as by wearing pants.

Quote of the day: Live out your imagination, not your history.” Stephen R. Covey

How to style midi skirts and boots
Midi Skirt Facts
Tall Boots
Contrasting skirt and boots
Print skirt and neutral boots
Solid skirt and neutral boots

Maybe your history is all about wearing pants because that is the habit you’ve gotten into. But I hope to inspire you to consider wearing midi skirts and boots. Not only can it be just as warm in the winter, but you will have a wonderfully stylish look instead of blending in with all of the other women wearing pants.

Now if you don’t have any midi skirts in your closet and don’t want to spend a lot of money, then preloved skirts could be the perfect answer. And if you prefer to shop online, here is a short list of my favorites:
thredUpthis link gives you $10 (and me in return).
Poshmark — here is the post about how to shop the site.
Uncommon Closet— nonprofit to help women.
Gild the Lily–a local Michigan store that sells online.

You should definitely sign up for the emails below. Besides the free eBook, my email family gets personal tidbits of what’s going on in my life along with other happenings, sales, information, giveaways, extra photos, and interesting articles.

Let’s Talk About Midi Skirts

Look, I know there are many of you who remember the days when you were only allowed to wear skirts and dresses. And most women I see in my retirement community have switched to pants. Is it because pants weren’t allowed back in the day? Maybe it’s a rebellious thing?

It certainly can’t be a comfort thing because skirts are much more comfortable when you consider the facts.
1-There are very few fit points in a skirt. For instance, in an A-line skirt, you just have the waist and length (and really the length can be very varied. A couple of inches here or there doesn’t make the same difference it does with pants). You don’t have to worry about if a skirt is too tight around the thighs. This also makes it wonderful if you happen to be changing sizes. I have a skirt that still fits from over 30 years ago as seen here.
2-Because there is no material between your legs, you don’t worry about irritation or tightness in the crotch area.
3-And let’s talk about the bathroom thing. You don’t have to worry about your pants pooling on the bathroom floor. (Even if you are wearing tights, they are usually tight enough to stay above your knees).

For those of you who complain about chub rub in the summer, then winter is the perfect time for midi skirts and boots because you can wear tights or leggings which will counteract the chub rub.
If you hate wearing tights because you think they are uncomfortable, have you tried them lately?? With the advent of spandex and newer materials, you might be surprised.
And for those of you who live where it’s really cold, then you should try the fleece-lined tights. They are much warmer than pants!

Insider tip: Don’t think that your midi skirt has to be made from a “winter” material. If you are wearing fleece tights, then the skirt can be for decoration. For example, when Charlotte wore a lightweight skirt with a sweater long ago and was surprised because she had never thought to wear it with a sweater and boots.
This goes along with my motto to stop categorizing our clothing. Stop calling it winter and summer clothes. Most summer things can be transitioned into winter wear with the right layers.

Now the wonderful thing about midi skirts is they are long enough to provide coverage and they are still very easy to sit in. Heck, you can even spread your legs without worrying about showing off your undies.

Related posts: Midi dresses for casual
Midi satin skirt outfits

Boots Are Made For Walking

Now let’s discuss boots. Even living in Arizona, I have a boatload of tall boots because they really and truly keep you warm. Plus the advantage of tall boots is you really don’t have to worry about if your socks match or look good with the outfit.

Tall boots are the perfect combination with midi skirts because they bridge the space between your feet and the skirt hemline.
For warmth galore, you could be wearing fleece-lined tights under the skirt and even have a pair of wool socks on under the boots.

Insider tip: I routinely order a half-size bigger in my boots so that I can double up on socks or choose thick wool socks.

Now let’s talk about 3 different options of midi skirts and boots and how to create a stylish look.

Contrasting Skirt and Boots

Red denim jacket for older women
Skirt: Bella Page~~ Jacket: Las Olasa-thrifted~~ Top: Chicos~~ Boots: no label ~~ Scarf: Purse: NL-thrifted

Lesley wore contrasting colors with her skirt and boots. In fact, you’ve seen these boots before worn with leggings. Lesley wasn’t sure if the boots and voluminous skirt went well together because of the bulk from the bunched shaft of the boots. I would like to say that they go fabulous together. Sometimes we can overanalyze things way too much.

Insider tip: Color is the detail that humans notice first and foremost, so while balance and proportions can be important, they aren’t the first things we notice.

Lesley also knotted the hem of the sweater to make it more fitted and shorter. This is a wonderful trick to help with the balance of the look. Since the jacket is boxy and the skirt is voluminous, it’s nice to have the shirt fitted. And if the shirt you want to wear is not fitted, remember you are the boss of your clothes and can make it such.

The Extras

Lesley also chose a print scarf and a print purse to add pattern to the look. Both of the print items have more than just the colors of the outfit in them which gives the outfit more depth.

Scarf: This is a short rectangle scarf that Lesley just folded lengthwise a couple of times and tied behind her neck. Basically, she is creating a fabric necklace.

Wearing red in winter with midi skirts and boots

Print Skirt and Neutral Boots

Yellow leather jacket with red plaid midi skirts and boots
Skirt: Pendleton-thrifted~~ Jacket: Zara-thrifted ~~ Top: Mom made it~~ Boots: Charter Club ~~ Purse: no label

Charlotte wore a print midi skit and neutral-colored boots. The red plaid of the skirt has black in it, so wearing it with black boots seems very easy.

If you get my emails, then you saw the original jackets my mom was going to wear with this midi skirt and boots. It seemed very matronly, so I twisted her arm to wear this yellow leather jacket instead.
In my opinion, the yellow leather jacket gives the outfit a more modern vibe and adds personality to the look.

The Extras

My mom wore garnet earrings to pull the red of the skirt up to her face. She’s a sucker for anything garnet since it is her birthstone.
And you can see with the print purse, she is incorporating some print mixing with her look.

Color combination of yellow and red for a stylish outfit

Solid Skirt and Neutral Boots

Midi skirts and boots for winter looks
Skirt: Target~~Sweater: Fashom~~ Top:~~ Boots: Target~~ Bracelet: Sally Hoffman Designs ~~ Purse: Myra Bags~~Hat: Amazon

My option with midi skirts and boots was to wear a solid-colored skirt with neutral boots. The white cowboy boots have been my huge favorite this year as I’ve showcased how to wear them in multiple ways.

My silk slip skirt is definitely not what I would consider a warm material for the winter months. But I can hide layers under it easily. Heck, even under the shirt and sweater, I could wear long underwear if I needed to.

Insider tip: The denim shirt is actually a collared shirt, but I felt that the collars took away from seeing the beauty of the necklace. So I tucked them inside instead. It’s no different than how I did this trick with another shirt in this video.

Since all of the clothing items were solid colored, I added prints and other colors to the outfit with my necklace, purse, bracelet, and glasses.

The Extras

I don’t think I have the ability to wear a solid-colored sweater by itself, haha. Seriously, I get all twitchy and have this need to accessorize. That’s why I added this incredible necklace that I found at the Mesa museum recently. It was made by a local artist who has since passed away.
Looking back on these photos, I might have liked the look better with a white blouse under the sweater, but hey, it’s all good.

Salmon and burgundy colors together in an outfit

Burgundy and Peach Color Combination

This is a color combination that I don’t see together often, yet both burgundy and peach are warm colors that look great together. When you combine two colors together that you aren’t sure about, then finding something that has the two colors in it can pull it all together. For my outfit, the purse basically does that.

Winter options of midi skirts and boots
Midi skirts and boots

Photo credit: Rob Filogomo

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Thank you for visiting my space on the internet. I like to showcase how it’s never too late to look great for women of any age, size, or working with any size of budget.
I feel I’m here to help move beyond the fashion rules of yesterday and evolve. Style and clothes are made to give you joy. Not cause us stress because we are worried about what others think.

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