Modern Ways To Style Booties Over 50

Are you as fond of wearing booties as I am? They’re so much warmer than shoes this time of year and help keep our feet dryer in the soggy weather. Let’s have a look at some modern ways to style booties over 50.

pink sperry rain boots in puddle
blonde woman wearing rain booties and matching trench coat

I bought these water-resistant rain boots at the Nordstrom anniversary sale 3-4 years ago and haven’t needed them until this week! We’re being deluged with torrential downpours and blustery winds, so these Sperry Saltwater Duck Boots (this year’s version) are finally perfect!

over 50 blonde woman wearing pibk rain coat and rain booties

The laces don’t tie, so they’re easier to slip on and off and are still snug on the foot. A skinnier pant leg would work better for tucking into boots, especially if you tuck them into your socks first. This is what I was wearing when the rain hit, and we ran outside to grab some photos. It’s also fun to swear cuffed socks over the skinny pants that show above the booties.

Straight and bootcut jeans are perfect to wear over booties. The hem of your jeans should cover the arch and down to where the heel meets the boot at the back of your heel and even longer if it’s a high heel.

The newest crop of water-resistant suede boots like mine above means you can wear them rain or shine.

You may also enjoy – How To Wear Ankle Boots Over 50

Jennifer Connolly of A Well Styled Life wearing Eileen Fisher Booties

I have 5 pairs of black ankle boots, all with different levels of refinement (that’s my justification), and I am now looking to add ones in my current hair color.

*STYLE TIP – Wearing footwear in your hair color keeps the eye moving around your silhouette, which draws attention back to your face. It bookends any outfit you wear.

Stiletto heels are not in my wheelhouse these days, but generally, the higher and skinnier the heel, the wider the pant leg needs to be.

woman standing with bib of jacket showing

There’s no question that pointed toes elongate the look of your leg, but I find almond or round-toe boots are comfier when wearing socks for warmth. Almond is a timeless toe shape that’s always in style.

This year, I’ve embraced boots and shoes with stretch, which are super comfy, and am just choosing the low block heel, which is the most stable and preferable for my aging feet.


  1. I just found you on Pinterest. It’s nice to see women of a certain age dressing with style. I’m 62 and love to play with clothing without trying to dress like my 28-year-old daughter. Great boot/pant tips!

    1. Welcome, Kati! I’m happy you’ve found us here.

  2. Bev and Val from Seasons Embraced says:

    Love the Joss Knit Booties by Eileen Fisher. Did not even know about them. That heel is the best for on your feet all day and still want great style. Thanks for the post.

  3. I love boots of any kind. Thanks for the styling information.
    Especially tucking pants into my socks
    Cool trick that keeps you warm also.
    Hair still looking good.

  4. Love booties, they are comfortable and so stylish. It’s gotten a bit cooler here in central Florida so I have the opportunity to wear them. But then again you never know tomorrow could be back in the 80s.

  5. Jan Correll says:


    I am all about those snake print booties and adding them to my shopping list. Thanks again for the invite and can’t wait to work with you again.


    1. Thank you for joining us, Jan. I love your attitude and style.

  6. Great post. One comment: I know the Sperry’s have the curly lace endings and that if you are cool, you don’t tie them. But when it rains or snows and your boots are slipping, just pull the laced together and tie at top. Don’t undo the curliques! We can all go back to being cool once the rain stops, right? -:)

    1. Good tip. I didn’t know that about the laces. Thanks!

  7. I’ve been following you for a while, and enjoy all your suggestions. Because you’ve decided to go all gray and your hair is a ‘bit thin’ as you mentioned, I have a suggestion: my dear friend does some low lights in her hair (a darker gray)and it looks amazing! Just a suggestion! Merry Christmas! 🎄

    1. Thank you, Michelle. Great idea!

  8. Boots are really a staple now, especially in the Northwest where I live. I have all kinds too.

  9. Jan Kofoe says:

    “They” say we instinctively like the colors that look best on us but I never associated it with my shoe color. I have warm brown hair (no gray at 72!) and I have 4 pairs of booties in those warm brown color ranges. Glad to hear I’m right on target. Great post about how to wear booties. I was slow to embrace the look because they are a little difficult to coordinate with pant legs so thank you for the tips!

    1. Yay! Many if us seem to instinctively know and I think we should follow our hearts.

  10. I am drawn to booties this year like never before. I can definitely see why you have 5 black pair, and some in other colors too! They seem a bit more elevated and interesting than anything in my collection of flats. Thank you for pointing out that the Eileen Fisher knit shoe comes in both bootie and loafer. That’s when I started noticing my preference for booties this year. Thank you for your posts, I’m learning a lot and having fun reinventing my style as a new empty-nester who has recently moved to a larger, vibrant city.

    1. How fun to move to a vibrant city! We really enjoy our time spent in downtown Vancouver.

  11. I love your boots. I have a new pair of ankle boots. I have boney ankles. What do you suggest wearing with them, so they don’t rub my ankles?

    1. Cozy socks that cover and protect.

  12. Yes, you have discovered one of the reasons skinny and slim pants should stay: winter boots! I’m talking serious knee-high boots for heavy duty warmth in snow. Pants need to be tucked in under these conditions, or a lumpy, bumpy leg look ensues.

    I’m sorry you are having an atmospheric river.

  13. All these are so pretty. I love the pink trench coat with pink boots so much and wish I could do that but I need to stick to neutrals. I didn’t realize that about the hair but makes sense. So, I’ll look for something in a silver bootie or at least silver buckles. Love the pearls! Well that complete outfit. You look perfect in it.

    1. Thank you, Eve. I’ve always gravitated to black footwear but taupe and metallics are best for me now.

  14. Thanks Jennifer, you always have great ideas. I love those cute duck boots!

    I don’t see a post today from Silver is the New Blonde. Most recent appears to be Dec 9. Am I missing something?

    1. Sorry, Jan is having an issue getting her post out. Hopefully soon. She’s a very cool lady.

  15. I just can’t develop a fondness for booties. I see them all over the web and blogs, and I have a pair, but I just don’t care for the look. I’ll go for a riding boot most any day of the week in winter, but the booties are just not a look I can feel comfortable with or in.

    1. We’ve got to wear what we love!! Happy Tuesday

  16. Love the Eileen Fisher knit booties and I have always admired those favorite black booties of yours. They have such a flattering cut. Now you got me at hello on that gray waterproof puffer…darling cut and so flattering. I could get into a lot of trouble with this post. We always have fun with these topics!

  17. I live in Arizona…warm and dry so never wear booties unless I am traveling somewhere else.

  18. Am finding these days due to my age and having back issues lately plus the climate I live in; am leaning more to wearing loafers or a slip on shoe if weather permits rather than a bootie or opt for at least a high knee to mid-calf zippered boot that I pair with either leggings or a midi skirt/ dress rather than wear even leotards/tights. Great tips though for those opting for them! -Brenda-
    P.S.: Have forwarded the (Helen Mirren) hair style photos to you.

    1. I hope your back feels better, Brenda. That’s painful. Thanks fir the pictures. Super cute

  19. Loved this post, I enjoy wearing ankle boots with pants and jeans. I saw the snakeskin on you and ordered a pair!! Excited to try them !!

    1. They’re really comfy and I find the print very versatile.

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