Riding Boots 2 (On the Outside)

50’s                        60’s                      70’s

Riding boots for the 50's, 60's & 70's

Riding Boots for the 50’s, 60’s & 70’s: On the Outside

Quote of the day: “A wise system of education will at last teach us how little man yet knows, how much he has still to learn.” John Lubbock, Sr.

Since you most likely paid extra for a taller boot (as opposed to an ankle boot), you might as well show it off!  One of the modern looks for a riding boot is to tuck your jeans into them.  If you want to try this, just make sure the jeans are close fitting throughout the leg…it looks funny to have extra material pouching out on top of the boot.  Practical tip: Tucking your jeans into your socks first makes the entire process easier!   Visit Riding Boots 1 to see these same boots paired with dresses!

Riding boots for the 50's, 60's & 70's Riding boots for the 50's, 60's & 70's

50’s Riding Boots: I was never going to buy red jeans thinking they were too young for me…but, really, why would a color be off limits to an age group?  And this necklace?  It’s reversible….same design, but turquoise on the other side!

Boots: Naturalizer (here)~~Jeans: (similar here)~~Jacket: (similar here)~~T-shirt: (similar here)~~Necklace: (similar here not reversible)~~Earrings: (similar here)

Riding boots for the 50's, 60's & 70's Riding boots for the 50's, 60's & 70's

60’s Riding Boots: Since Nancy’s boots are burgundy, I kept the top half of the outfit in the same burgundy color scheme.  I knitted this sweater for myself first, but then gave it to Nancy since it looked so good on her (then I made myself another one)!

Boots: Enzo Angiolini (similar here)~~Jeans: Gloria Vanderbilt (similar here)~~Cardigan: I knitted it (similar here)~~T-shirt under: Sonoma (similar here)~~Earrings: (similar here)

Riding boots for the 50's, 60's & 70's Riding boots for the 50's, 60's & 70's

70’s Riding Boots: The riding boots also work fabulously with leggings!  We then add a punch of color by donning the burgundy cardigan sweater!

Boots: (similar here)~~Leggings: Apt. 9 (similar here)~~Cardigan: (similar here)~~Sweater under: (similar here)~~Necklace: (similar here)~~Earrings: (similar here)

Thanks for visiting my styling blog!

Some photography by Kari Strand Photography

Riding boots can be one item that is easier to order online–you can always order them slightly bigger and wear heavy socks with them!


  • Kathleen McDermott

    All of these outfits are well done. Cozy, stylish and flattering. Your necklace is gorgeous, and I love the sweater you knitted and Charlotte’s long sweater. Charlotte’s earrings are so cool.

    • Jodie Filogomo

      Thanks Kathleen.
      This is one of my favorite sweaters that I’ve knitted—it must be if I knitted a second one just like it because I never do that!!

  • Lovely post. I love riding boots and it goes so nicely with skinnies

    Made in Mauve // Bloglovin

    • Jodie Filogomo

      Thanks! My mom wasn’t sure as a 70 year old, she should wear it…but I believe this trend is ageless!!

  • Riding boots and skinnies are definitely a great go-to winter look. So many possible combinations, and they all look great.

    Chic on the Cheap

    • Jodie Filogomo

      Thanks Lydia!!!

  • versatilestylebytracey

    Tucking skinny’s and leggings into riding boots is my favorite thing about winter.. An assortment of flat boots really help when my sciatica is flaring up… I love all the reds and burgundy styled here. The knitted sweater is fantastic and I had to laugh that after giving it away, you made another one for yourself…

    • Jodie Filogomo

      Funny, huh? I don’t usually knit the same pattern twice, but I really did like the sweater and I had enough yarn…

  • Darlene Fadem

    The sweater that you knitted is beautiful!

    • Jodie Filogomo

      Thanks….It was an easy pattern, it’s the yarn that makes it!

  • Guest

    That sweater you knit is beautiful!