3 Decades of women's style

How to Wear Booties: Classic Black Footwear with Variety

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When Bo of our Ageless style group suggested how to wear booties for our monthly theme, I figured the three of us would show 3 different ways of styling black ankle boots.
Aren’t black ankle boots something classic? They certainly are something any woman can wear whether for casual days or dressy events.

How to wear booties with jeans
How to wear booties with leggings
How to wear black booties with white jeans

Quote of the day: “Know what you want. Follow a trajectory where what you want is a possible outcome. Build a system to incrementally improve your ability to follow that trajectory. Trust yourself. Enjoy the outcomes. Repeat.” James Clear

3 ways of how to wear booties

I figured the three of us showing how to style these black booties are a perfect trajectory to give you more variety in your closet. We all want to look stylish. Sometimes, we get stuck in some ruts about what to wear. This is why it’s so fabulous to support blogs so we can get so many different kinds of inspiration.

We are starting with two classic and basic ways of how to wear the black booties, and then I include an outfit where they act as a pop of color.

How to wear booties with dark denim

Jeans: Bill Blass~~ Jacket: Talbots-thrifted ~~ Top: Zara ~~ Boots: Soft Style~~ Earrings: Charming Charlies~~ Purse: no label

Black Booties with Jeans

Charlotte has a pair of wedge black booties that even have a buckle at the ankle. The buckle or any kind of decoration like this does not mean you have to show off the entire bootie. It can certainly be hidden under a wider type of jean silhouette like my mom is wearing here.

This pair of darker denim jeans is a pair that you’ve seen her wear recently with a t-shirt and loafers. I referred to them as wide-leg jeans, but they could also be considered a boot-cut silhouette. What is more important than the name of a style of jeans, is how they fit and how it is paired for the overall look.

You can see Charlotte wearing these same booties with black straight-leg pants here.

Insider tip: If you have a hard time pairing navy and black, then the varieties of darker denim might be a great baby step. Some of the darker denim seems almost black. Don’t get caught up in that old rule saying you shouldn’t wear navy and black together. Why shouldn’t the two colors play together?? Some of those old rules have no reasoning behind them.

And just because you’re wearing jeans doesn’t mean you have to be sloppy. My mom is sprucing up her jeans with a whimsical polka dot blazer (worn here with other polka dots) and then she added in a vibrant green top under the blazer.

This green top is actually a crop top that my mom purchased on our field trip to Zaras. I LOVE that it’s shorter and the color is fabulous on my mother. Just because it’s fall and winter, don’t give in to only wearing dark colors. This is the time of year we need to be uplifted since the days are shorter.

Accessorizing for Jeans and a Blazer

The accessories pull everything together and make it all look intentional. The other thing accessories do for this specific outfit is casualize the blazer. Too many times we think of a blazer as work-oriented or serious. So by adding colorful accessories, the look becomes more playful and approachable.

The green earrings were a budget find at Charming Charlies before they went out of business. The nice thing is they are plastic and therefore very lightweight.

Insider tip: Charming Charlies is online now if you need your fix.

And the colorful purse really creates a modern vibe to the overall look, especially with the print blazer. Using your purse to add another print to the outfit is one of the baby steps we’ve discussed in the past.

How to wear ankle boots with leggings

Leggings: 1Zone~~ Kimono: I Joah~~ Top: Chicos ~~ Boots: Franco Sarto~~ Necklace: ~~ Purse: Target

How to Wear Booties and Leggings

Lesley is showcasing another classic style option of how to wear booties and leggings. Matching the color of your leggings with ankle boots helps carry the same color from waist to toes. Most older women feel very comfortable with this option and then you can add fun colors or prints with the top half of the outfit.

Insider tip: Matching your boots to your pants/leggings can be helpful if your top is long and thus creates a half and half proportion without the footwear. The addition of the same color of the boots/shoes will help elongate the proportion factor.

For the colder months when you don’t want bare ankles showing, just add in a matching pair of trouser socks under the leggings. BTW, there are even fleece-lined trouser socks available.

Insider tip: ANY woman can wear leggings. Lesley shared this: “people think fluffy (overweight) ladies shouldn’t wear them but I cry foul and do it anyway.”

Kimono for Colder Months

Lesley is wearing yellow and a striped, long kimono with her leggings. I love that yellow can be a color for the fall and winter seasons since it’s such a happy color.

You may not realize that the striped garment is a kimono. It’s a good example of how cardigans and kimonos could very well be interchangeable.

Insider tip: If you always run warm, pull out the summer kimonos instead of the heavy cardigans.

Lesley’s statement necklace is a wonderful way to break up a solid t-shirt. She has worn this necklace many times on the blog because it adds a wonderful focus to the top half of an outfit.

Add a pop of color with black ankle boots

Jeans: LOFT~~ Sweater: Vine & Love bought from Naomi & Ruth Boutique~~ Boots: Shoedazzle~~ Scarf: I knit it~~ Necklace: LOFT~~ Purse: no label

How to Wear Booties as a Contrast with White Jeans

I always love the idea of having our footwear being a pop of contrast to the overall look. Since we were showcasing black booties, therefore, I grabbed my beloved white jeans.
White jeans are my favorite in the winter because they can pop the darker colors we tend to wear in the colder months. In fact, the original trio showcased this many years ago.

Insider tip: I’ve had the best luck with LOFT white jeans. They are thick and not see-through. I also like the no-stain Chico’s white jeans, but I always have to alter the waistband of that brand.
Yes, I have more than one pair of white jeans. Maybe more than 2, haha!!

For this example, I wanted to show something different than a black and white look. So I wore a pink, fuzzy sweater that I bought last season from a local online boutique. The color combination of pink and white could feel too springy which is why the boots and accessories can make all of the difference.

You can also see another idea with wedge-type black booties with my faux leather leggings here.

Tying it All Together with Accessories

I carried through some darker elements with my accessories. The infinity scarf is hand knit by me from alpaca yarn. This is a special alpaca yarn because it’s from my friend’s own alpacas.
Notice the scarf isn’t black like the booties but has dark brown and charcoal grey in it which still looks wonderful.

I’m layering the scarf with a longer necklace which shows you aren’t limited to only one accessory around your neck.

Other examples of scarves and necklaces together:
Practical Reason Layer a Necklace and Scarf Together
How to Accessorize a Boat Neck Tee
Tested and True Choices for a Necklace for Cowl Neck Pieces

I did match my purse to the black ankle boots for this example. The purse is a favorite find at a shop in the Las Vegas airport. In fact, my mom found it and twisted my arm to buy it. It’s made to look like the front of a black leather moto jacket, and it’s the only black purse I own (besides a couple of vintage clutches).

So if you are going to carry your black purse, why not have it be an interesting black purse?

Black Booties

If black booties are something you wear a lot, I think it’s smart to have both casual versions and dressy versions. Even if you don’t wear heels, a patent leather option can work for those fancier events.

Yet I hope this post has given you ideas of how to wear your black booties. Don’t be limited by our examples though. I truly think there isn’t a color you couldn’t wear with them. Sometimes the extra pieces of the outfit can tie everything together and create an intentional look.

Have fun with your black booties because they are so versatile.

How to wear booties for any age

Ageless Style & How to Wear Booties

The Ageless Style group has had some changes in its members. I hope you pop over to see how they styled their how-to-wear booties posts! I always find so much inspiration from each and every one of them. But we don’t all post at the same time so make sure to check back if their post isn’t up yet.

Ageless style

Amy ~ Amy’s Creative Pursuits
Blog Instagram | Pinterest | Facebook |
Bo ~ Bo’s Bodacious Blog
Blog / Instagram /Pinterest / Bloglovin’
Carrie ~ A Simple Lovely Life
Blog | Instagram Pinterest | Facebook |
Daenel ~ Living Outside the Stacks
Blog | Instagram | Pinterest | Facebook |Twitter |
Joanna ~ My Slice of Life
Jodie ~ Jodie’s Touch of Style
Blog | Instagram | Facebook |
Leslie ~ Once Upon a Time and Happily Ever After
Blog | Instagram | Pinterest | Facebook |
Marsha~ Marsha in the Middle
Mireille ~ Chez Mireille Fashion Travel Mom
Blog | Instagram | Pinterest | Facebook |
Robin ~ Hello I am 50ish
Blog / Instagram / Pinterest / Facebook

Finding variety in how to wear black booties

Photo credit: Rob Filogomo

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