The Complete Guide to Styling Boots | Women Over 50

Shop This Look: I am obsessed with my new Sheridan Boots by Miz Mooz I bought these Distressed Jeans by Spanx last year and wear them all the time. Perfect for wearing with boots because they don’t ride up and create a long lean line and my Reiss sweater is super cozy and can be styled several ways.

One of my favorite things about fall and winter is styling boots for women over 50. I love boots and wear them often, even though we only wear boots for two months or so here in Florida, I have always loved the look of boots with jeans, trousers, skirts, and dresses.  Through the years I’ve collected several pairs and look forward to wearing them as soon as the weather begins to cool—even though I am often the only person wearing fall clothing here in Florida.  I love celebrating the season’s change in my home and wardrobe.

I love creating outfits with suede, and leather boots as well as over the knee boots, knee-high boots, and booties.  Heel heights also considerably change the look of the outfit as well.  Here, we will style several boot looks, and answer many common boot questions women over 50 ask when considering styling outfits with boots.  

Some people ask:

What month do you start wearing boots?

Boots can be worn year-round, (some wear cowboy boots throughout the year, for example). Generally, however, women begin wearing boots as the weather cools through to the end of the rainy season in spring.  In early fall boots are mainly worn stylishly, but in cold climates boots are worn for practical reasons insulated boots with special soles to help prevent slipping are an important part of keeping warm, and dry.  When choosing boots for practical use, one much considers the purpose of the boot and the type of weather and terrain you plan to wear them in.

Can women over 50 wear booties?

The short answer is yes, women over 50 can wear boots and booties.  There has never been a fashion “rule” prohibiting women over 50 from wearing boots or booties.  In fact, booties have been very popular among women over 50 because they are often designed with a lower heel and are both comfortable and practical.  They also fit and flatter all figure types and can be worn with many different outfits.

Can women over 50 wear over the knee boots?

Women of any age can wear over the knee boots, though over the knee boots tend to be less popular than other boot styles among older women.  Worn with leggings in a matching color, over the knee boots can elongate the leg and make the wearer appear taller, slimmer, and more youthful.  However, the fit of the boot can be tricky, and styling outfits with over the knee boots can also be more challenging.   Women over 50 may consider over the knee boots to “youthful” or “trying too hard to appear young” but styled properly, they can be quite elegant.

How to wear knee-high boots over 50

Through the years, knee-high boots have been very popular worn with both pants and dresses.  Women of all ages wear beautiful knee-high boots.  Knee-high boots can create both casual and elegant looking outfits.  Knee-high boots are an important element of a classic wardrobe.

Style Tips: Styling Boots For Women Over 50

1. To create a long slimming look, keep your color palate mono chromatic, match your boots to your pants or skirt.
2. Pay attention to heel height.  A slight heel will elongate the leg and flatter more than 
3. Pay attention to the toe of the boot.  Open toe booties have been very popular, pointed toe boots create a more elegant line than rounded toes
4. As always keep your boots in good repair, use a suede brush to keep suede looking new, make sure to spray your boots with protectant if you wear them in rain or harsh weather conditions.
5. Pay attention to the length your pants and skirts in relation to the top of your boots and booties.  Too much of a gap can shorten the leg.
6. Take care when paring booties and skirts, this combination can make the ankle look thick.  

It may seem a bit overwhelming but these tips are so important when styling boots for women over 50.

Styling boots with skirts and dresses:

When styling boots for women over 50, proportion and line are the two most important factors when choosing boots for your outfit, and most of the time, keeping the color palette cohesive is the best strategy for creating an elegant look.

Wearing booties with skirts or dresses can be tricky as they can make the leg look wide or short. Wearing a super-short skirt with over the knee boots can be amazing or it can be a little too much, so when you consider your outfits be sure to try everything on to make sure it looks the way you want it to.

Looking for more styling tips? Check out these posts:

Chic Ways of Styling Cardigan Sweaters This Fall

This Season’s Best Sweaters for Women over 50

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Check Out My Stylish Monday Friends:

Ask Suzanne Bell – Everyone needs a classic boot; a workhorse that you can wear every day, day or night – season after season. I own 2 pairs of this classic block heel boot, one brown, the other black from Tory Burch. And though they look alike, they are actually quite different. Yes, they DO have the same heel (which I LOVE), but the brown pair is a slouch tall boot – the black, a side zip classic black boot. I rarely purchase anything in doubles, but these boots are that good.

Nancy’s Fashion Style – I adore boots and especially ankle boots! These gunmetal ankle boots are one of my favorites! Actually, I love all of my ankle boots. It’s an addiction, lol.

Pearls and Pantsuits – I’m styling my absolute favorite taupe suede block heel boots. I’ve had them for several years and love them for both their versatility (I mean…the color goes with everything!) and their comfort! I have a wide calf, so finding boots to fit is a challenge for me. I don’t mind splurging when I find a pair that fits!

High Latitude Style – It was like you switched a button. From one day to the other fall turned to winter – Alaska winter. We are breaking one negative temperature record after the other. Today in the morning, it was -32C (-25.6F). The old record was -24C (-11.2F)  in 1999. The average high is -5C (23F) and the average low is -13C (8.6F). Well, obviously, that’s the weather, not climate. And it means boots are a Must when you want to wear a skirt. Well, I am a hard-die skirt and dress gal. Thus, I bite the bullet.

Style Splash Boots are my favorite type of footwear and I have many pairs in different styles and colors. I usually prefer darker colors but I’d been looking for a pair of white or cream knee boots for a while when I spotted these on sale. They were too good to resist! I really like the chain detail on the heel…and they make a change from brown and black!

Fashion Trends and Friends – Can a girl have too many boots?  Why of course not!!!  That poses a dilemma as to which to post for this month’s theme as I love all types of boots and have various styles in various colors!  I opted to share several boot styles that I thought I’d never wear…never say never!  I thought I’d never wear over the knee boots as I felt they made the tops of my thighs look too thick – like muffin top but thigh top – LOL!  I know I’m late to the OTK boots but hey better late than never.  I also thought combat boots weren’t for me.  While I thought others could pull them off well, I just wasn’t feeling them.  That is until I found a Jessica Simpson embellished pair with rhinestone buckles!  If it sparkles and shines, I’m all about it!  

Shelbee on the Edge – Boots are my very favorite footwear ever. I am always drawn toward bold statement boots, too. It was so hard to choose which pair to feature for this month’s theme, but I finally settled on these over the knee lace boots from Shoe Dazzle, one of my favorite places to shop for shoes. I bought these a few years ago and they were really tight around the calves, but after losing a few pounds they now fit perfectly. I paired them with a long-forgotten taupe chiffon and lace dress from a few years ago. Recently, I have not had much reason to get dressed at all let alone dressed up, so I used this style prompt as a reason to go all out dressy! 

Elegance and Mommyhood – Oh I am dying over this boots+booties post because that’s what I wear for 6 months here in Michigan. Today I styled my new faux suede taupe ruched boots by Target in a monochrome grey+taupe look that matches my leafy background. These boots looked so good with my grey moto jeans from Nordstrom (old) and my leopard tunic sweatshirt by Abercrombie (new). The mauve mini velvet crossbody bag added an additional texture to the look and I love the mild print-mixing with my herringbone newsboy cap.

Nancy –  Nancy’s Fashion Style – The white boots are for the collage. The gun metal ankle boots are for your posts. My blurb: I adore boots and especially ankle boots! These gun metal ankle boots are one of my favorite! Actually, I love all of my ankle boots. It’s a addiction, lol.Emma – Style Splash Boots are my favourite type of footwear and I have many pairs in different styles and colours. I usually prefer darker colours but I’d been looking for a pair of white or cream knee boots for a while when I spotted these on sale. They were too good to resist! I really like the chain detail on the heel…and they make a change from brown and black!

Julie – Fashion Trends and Friends – Can a girl have too many boots?  Why of course not!!!  That poses a dilemma as to which to post for this month’s theme as I llove all types of boots and have various styles in various colors!  I opted to share several boot styles that I thought I’d never wear…never say never!  I thought I’d never wear over the knee boots as I felt they made the tops of my thighs look too thick – like muffin top but thigh top – LOL!  I know I’m late to the OTK boots but hey better late than never.  I also thought combat boots weren’t for me.  While I thought others could pull them off well, I just wasn’t feeling them.  That is until I found a Jessica Simpson embellished pair with rhinestone buckles!  If it sparkles and shines, I’m all about it!