Daring Style For Riding Boots With Dresses

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One item in most of our closets should be the riding boots, especially if you live in a region that experiences colder months like here in Denver!  

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

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.

Why is it daring?? Because women of my generation don’t realize that riding boots and dresses are a fabulous option together. But here we are with 3 options for grown women and fabulous looks.

Jodie’s Outfit

riding boots for the 50's, 60's & 70's
Boots: Naturalizer (here)~~Dress: (similar here)~~Cardigan: Boden (similar here)~~Earrings: (similar here)~~Necklace: Made by Gayle (similar here)

So I won these boots from Naturalizer in a contest last year and was excited to style them.  I went with a quirky look of contrasts for this outfit: a girly dress with the more casual, almost clunky boots!

riding boots styled with a dress

Wearing two different styles like the floaty dress and heavier riding boots is how to create a dichotomy in your look. Think of it like yin and yang or mix and match.

Related post: I’ve worn this same dress in warmer weather with sneakers.

Nancy’s Riding Boots

riding boots for the 50's, 60's & 70's
Boots: Enzo Angiolini (similar here)~~Dress: (similar here)~~Sweater: Pure Handknit (similar here)~~Necklace: (similar here)~~Earrings: (similar here)

 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!

Blue earrings

This is the perfect way to winterize a summer dress. You could even layer a long sleeve shirt under it as well as wear the cardigan over top.

Charlotte’s Riding Boots

Woman in her 70s dressed in a skirt
Boots: (similar here)~~Skirt: Mom made it (similar here)~~Sweater: Le Chois (similar here)~~Shirt under: Rubbish (similar here)~~Earrings: (similar here)

This sweater is the focal point of the outfit!  The boots blend in quite well taking the blue from the chambray shirt.

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

My mom is incorporating some dichotomy into her look also with the denim blouse under the sweater. The skirt has a business vibe, but adding the chambray shirt makes it more casual.

Other ways we wore these same boots:
1-Wearing jeans tucked into them
2-Boots worn under jeans

Thanks for visiting my styling blog!

Some photography by Kari Strand Photography

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