Riding Boots 1 (With a Dress)

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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: With a Dress

Quote of the day: “The best reason for having dreams is that in dreams no reasons are necessary.” Ashleigh Brilliant

One item in most of our closets should be the riding boot, especially if you live in a region that experiences colder months like here in Denver!  Boots are great footwear for every foot/calf size, (there are many boot companies that tout wide calf sizes), age and budget!  Today’s post will concentrate on showing off the riding boot with a dress.

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

50’s Riding Boots: So I won these boots from Naturalizer in a contest last year (because I would rarely spend over $100 on a pair otherwise).  I went with a quirky look of contrasts for this outfit: a girly dress with the more casual, almost clunky boots!

Boots: Naturalizer (here)~~Dress: (similar here)~~Cardigan: Boden (similar here)~~Earrings: (similar here)~~Necklace: Made by Gayle (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:  These boots are burgundy in color which really pairs well with most neutrals.  The dress is short-sleeved so we added a cardigan for warmth!

Boots: Enzo Angiolini (similar here)~~Dress: (similar here)~~Sweater: Pure Handknit (similar here)~~Necklace: (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: This sweater is such the focal point of the outfit!  The boots blend in quite well taking the blue from the chambray shirt.

Boots: (similar here)~~Skirt: Mom made it (similar here)~~Sweater: Le Chois (similar here)~~Shirt under: Rubbish (similar here)~~Earrings: (similar here)

Thanks for visiting my styling blog!

Some photography by Kari Strand Photography

Wide calf boots to check out:


  • Kathleen McDermott

    Like Nancy’s, but love Charlotte’s and your outfits. Love your Naturalizers and Charlotte’s gorgeous navy boots.

    • Jodie Filogomo

      Did you read in a more recent post that my mom actually had these boots dyed? I thought that was so smart!! They were grey when she bought them, but she wanted navy ones—so the place offered to dye them for her (for a cost—but still)

      • Kathleen McDermott

        Wow. What a great idea. It’s hard enough to find navy shoes, I wondered how Charlotte found navy boots.

  • JOI

    such a cute & clever post. I LOVE the dress w/the riding boots!
    Check out my blog sometime 🙂

    • Jodie Filogomo

      Thanks Joi…I love your credo….it’s exactly what I want everyone to believe…we are all beautiful!!! Thanks for visiting!!!

  • Versatilestylebytracey

    I’ve always loved heeled boots with dresses, but this season I’ve embraced my riding boots with them out of necessity due to sciatica flare up.. I love all three of these looks and would wear them all.. 5o’s has a great boho vibe, which I adore. Who doesn’t love a striped dress and the bright cardigan makes me smile. Hoping at 70 I am as stylish.. just fabulous!

    • Jodie Filogomo

      I so know what you mean about the heels with dresses….but, as you reference, there is the need to be realistic, eh? Thanks for the love!

  • Perfect riding boots looks!
    Dresses & Denim

    • Jodie Filogomo

      Thanks Carly!!

  • Darlene Fadem

    The 60’s and 70’s looks have my name written all over them!

    • Jodie Filogomo

      That’s because you are so stylin’!!! 🙂

      • Darlene Fadem

        You are too kind.

        • Jodie Filogomo

          That sounds fabulous…I’m game!!! Make sure you wear/bring that embroidery skirt I covet!!!

          • Darlene Fadem

            You got it!

  • Jodie Filogomo

    Thanks for your input….mom tends to wear this sweater with a grey turtleneck under it…so I’m trying to push her to different ways!! It’s nice to know someone agrees with me! Maybe she’ll listen to you!!! Jodie

  • I love this! The last look is my go to style for work. I love layering collared shirts under a sweater! All super chic!