Ankle boots and jeans for fall

Chic Ways to Wear Ankle Boots and Boyfriend Jeans

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Inexpensive jeans

Chic Ways to Wear Ankle Boots and Boyfriend Jean

Today it’s all about ankle boots and boyfriend jeans. I had a request to showcase some of the new jean trends and keeping them fresh for us older women (thanks Susan for the idea). So stay tuned as we explore some of the not-so-crazy jeans styles that you can easily wear.

Quote of the day: “What’s my style is not your style, and I don’t see how you can define it. It’s something that expresses who you are in your own way.” Iris Apfel

Right now is a fabulous time to enjoy your ankle boots and jeans. Why? Because there are so many different options of styles of jeans available which means we don’t have to all look like a copy of one another. Just like Iris states, we are each our own person.

One of the biggest trends in much of the clothing right now is a looser fit and less body-hugging. While loose can seem sloppy at times, there are many ways to make it work. And I’ll discuss this below.

Let’s start with the jeans first.
Make sure to check out the difference between straight-leg jeans vs mom jeans. And see how wide-leg jeans can work on a petite woman.

Are Skinny Jeans Dead?

Let me just answer the elephant in the room when I talk about the new jeans trends. No skinny jeans aren’t “out” per se. I feel like they are going to be a classic style for years to come because there are many advantages to them.

Advantages of Skinny Jeans:
1-Tuck into tall boots easily
2-Pair perfectly with longer flowy tops like tunics
3-Spandex makes jeans SO comfy

Disadvantages of Skinny Jeans:
1-Depending on the material composition, you often get a saggy butt.
2-They can be constricting

Insider tip: I wrote a post about finding the perfect fit so you can say goodbye to saggy denim.

What we need to keep in mind with the new jeans trends is the silhouette is changing. And that can make it hard for us to like them because we are very used to seeing ourselves in skinny jeans (even though it took many of us years to embrace them, right?).

Remember, the more you see something, the more we think of it as normal. It’s a real thing called the mere-exposure effect. So start looking at all of the different silhouettes of jeans and finding what you might like best. This means trying on a LOT of jeans, but don’t make that a bad thing.

THE MOST IMPORTANT THING TO REMEMBER WHEN YOU ARE TRYING ON JEANS: YOUR BODY IS WONDERFUL. If the jeans don’t fit, it’s because they don’t fit. Not because there is something wrong with your body. If you need a reminder, go read my Perfectly Imperfect post because none of us need to be any kind of “er”.

For this post, I’m going to showcase the boyfriend jeans and I paired them with ankle boots.

Fall colors wearing ankle boots with jeans

Jeans: Old Navy Factory~~ Top: Banana Republic~~ Boots: Walking Cradles c/o~~ Scarf: Gibby’s Frillery ~~ Earrings: Audra Style c/o~~ Purse: Patricia Nash-won in an IG giveaway

What are Boyfriend Jeans

Boyfriend jeans are a looser fit than your skinny jeans. Yet they should still fit at your waist. The hips and legs shouldn’t be tight yet relatively straight. These aren’t too wide, yet just wide enough to skim the leg.

Many women like this style because it’s roomy through the legs and relaxed enough to fall in a straight line from hips to hem.

The other detail that is included with boyfriend jeans is that they tend to be more faded and/or distressed.

Insider tip: I recommend having all different washes of denim in your closet. If you always only buy dark denim, then all of your jeans will look too much alike.

Don’t get caught up in the name or category of a piece. If you check out all of the types of boyfriend jeans, they can all be so different! Just try on all different kinds of denim.

BTW, if you want to order jeans online, then order at least 2 different sizes (if not three). If you read my tricks and tips for shopping online, then you will know how important it is to check the return policy because you will be returning the ones that don’t fit. It’s silly to think you could order one size and they would fit perfectly.
Don’t forget alterations should be part of finding the perfect fit over half the time.

Chic boyfriend jeans style

Can Older Women Wear Distressed Jeans?

The short answer: YES!

Trust me, it took me years to feel comfortable in any kind of distressed jeans. Why should you even consider distressed jeans?
The big reason is it’s a modern detail. Even if you just start with the raw hem detail, it’s a great distressed option for women of any age.

Most of my friends turn their noses up at distressed jeans. I get it because I felt the same way for the longest time. But I think of it in the same way of how my grandma would NEVER wear pants. She continued to wear her house dresses no matter what because that’s what was in style in her heyday.
Wasn’t there something you wanted to wear when you were growing up that your parents didn’t like? I think of it that way too.

Change is a good thing, and snubbing our noses at the newer trends can be a recipe for frumpiness. If we have an open mind, I think we learn a lot more about our style.

What Top to Wear With Your Ankle Boots and Jeans

Now let’s talk about what to wear with your boyfriend jeans. Since they are not as tight as my skinny jeans, I decided to tuck in my top.

You know how I hate to give a rule, so I do think you could try this with an untucked top. Try all kinds of tops and silhouettes and take photos to give yourself some feedback. Remember I recently wore flowy bottoms with a flowy top and it turned out fun and artsy.

My suggestion is no matter whether your top is tucked or untucked, make it an interesting top. Our basic fashion training has us thinking that if we are wearing jeans, we should stick to something casual like a t-shirt. While that can work at times, it’s also fun to incorporate the idea of yin and yang in our outfits, this kind of dichotomy makes a much more interesting look.

That’s why I chose this silky orange top. It’s relatively simple, yet the flared sleeves give it some pizzazz.

Insider tip: If the flared sleeves seem to get in your way all the time, just shorten them. I shortened mine about 5 inches, and it makes them so much more functional.

Snakeskin booties with boyfriend jeans


Accessorizing is the way to take a basic outfit and make it more unique. For my ankle boots and boyfriend jeans outfit, I decided to forgo a belt and wear a “twilly” scarf on my belt loop instead.

What is a twilly scarf? I recently heard this term for the long, narrow scarves. Both the scarf on my belt loop and on my purse are Gibby’s scarves which are inexpensive versions of twilly scarves. My link gives you an additional 20% off.

Esthetically wise, I would have rathered put the scarf around my entire waist, but that’s not as functional for bathroom visits. Therefore, I tied it like this to give a vertical component to the look.

I also have a longer, Gibby’s scarf around my purse handle. You may think that the red print scarf doesn’t tie in with the outfit at all, but I think any extra color is good. It makes you stop and check it out.

Insider tip: Either scarf variation is a great option for wearing them in the hotter weather. It adds color and interest but isn’t too warm around your neck. If you have scarves, you might as well use them in your outfits!

Raw hem on jeans for older women

How to Style Ankle Boots and Jeans

Now to the shoes! Ankle boots and jeans go together like peanut butter and jelly. Especially in the early fall days when you don’t have to worry about snow, ice, and freezing cold temperatures, ankle boots are perfect.

If you have a stylish pair of ankle boots, then by all means show them off. What that means is you might need to cuff your jeans. This pair of boyfriend jeans have a raw hem, so I just cuffed them up once so you could still see the raw hemline.

Other options and don’t forget there is NO right and wrong way. Find the way that works for you by taking a couple of selfies to see how it looks. Remember to think about the proportion of the outfit. If your top is longer, you might want to try option #1. Then again sometimes the best outfits are when you break the rules:

1-Cuff the jeans under so there is no break in the color of the jeans before the boot starts. Most denim is heavy enough that it will stay tucked this way.
2-Double cuff so the cuff is half the width.
3-Make the cuff even bigger so you are showing more ankle.
4-Tuck the jeans into the booties. This works best when the jeans are skinnier at the ankles so you don’t get a pouf.
5-If it’s too cold to have exposed legs, try wearing socks that match your jeans or boots. I talked about this in my post 6 ways of wearing socks and boots.

Insider tip: If you’re looking for no-show socks that stay put, Sheec socks are my favorite. With an ankle boot like this, I wear the low or mid-cut variety.

Flare sleeves and boyfriend jeans

Animal Prink Ankle Boots

Animal print footwear is an easy way to keep your footwear fun. I have these same boots in leopard also, that’s how much I love them. These are the Shine booties from Walking Cradles and there are limited sizes still available. What makes them great for me is the under 3″ heel plus the comfort of the tiny pillows which all Walking Cradles shoes have in all of their styles.
If you have never tried Walking Cradles before, I can offer you a 15% off discount with the code, JODIE15. This brand is my gold standard for comfortable shoes now.

Animal prints should be in your footwear closet because they are composed of neutrals and therefore go with so many color combinations. Yet because they are a print, they are more interesting than your basic black or brown ankle boots.

Insider tip: My theory on shoes is that they can make or break an outfit. I understand the need for comfort which is why I work with many shoe brands to give you options. Even though your footwear only takes up about 1/10 of your outfit in the overall area, unless your feet are hiding under a table, people DO notice them.
You notice them too which is important in making us feel good! Since they are in our line of vision when we look down, they should make us smile.

Other Jeans Posts

Ankle boots with boyfriend jeans

Photo credit: Rob Filogomo

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