Timeless Wardrobe Essentials – Riding Boots

17 Nov

It’s no secret I love a great pair of riding boots (I declared my love for them in my very first blog post!). I think they are the most timeless form of footwear a woman can own. I was reminded of this in a past episode of Mad Men I recently re-watched where Betty was taking riding lessons. Although the program is set in the 1960s, the boots looked so timeless and sophisticated.

Why it is that riding boots can transcend trends and remain timeless no matter the decade? One reason I believe is because it doesn’t fall prey to heel and toe shoe trends. Pointy vs. round vs. square-toed, chunky heel vs. skinny heel. These characteristics, among many others have an effect on the timelessness of a shoe and indicate what time period the style originated. The riding boot, however, is generally immune to these trends. Classic riding boots always strike a balance between round and pointy toed and as a flat boot, you don’t have to worry about heel trends.

There are a lot of great riding boots out there – I particularly love the over the knee boots that women are rocking this season and last. Not to mention all the fabulous embellishments and hardware. While these characteristics are fantastic, they can detract from the timelessness of the boot. Below are some tips to ensure your purchase remains timeless:

Hardware/Embellishments – Less is more: The style of studs, zips and straps changes each season, so go for boots that have minimal or classic embellishments.

Shoe Material: Because you plan to get a lot of miles out of your boots, I would invest in an all leather boot (avoid suede because it’s less durable). Boots in synthetic materials can be cheaper; however these materials don’t wear as well as leather. Rather than just getting scuffed and broken in, synthetic materials can crack, flake, and strip away with wear.

Color – When choosing a color, stick with the classics: Black or brown. Not only are they timeless, but you will have no trouble finding a shoe polish to match those two shades of leather.

Here are some examples of riding boots I’m lovin’ this season and will be lovin’ them for the coming decades:

1. Me Too; 2. Frye; 3. Lucky; 4. Jessica Simpson; 5. Frye; 6. Tahari; 7. Etienne Aigner; 8. Aldo

So what do you wear with riding boots?

Riding boots look best paired with tight bottoms, such as leggings, tights and skinny jeans. If the bottoms aren’t very fitted, you run the risk of getting the bulge of fabric at the knee and ultimately looking sloppy. For some great examples of how to wear riding boots, visit my riding boot pin board for inspiration.


With winter right around the corner, it’s the perfect time to purchase a pair of riding boots. You will love the versatility and sophistication they add to your wardrobe!

xoxo, Andi

One Response to “Timeless Wardrobe Essentials – Riding Boots”

  1. Jim November 17, 2011 at 3:05 am #

    Your right, riding boots make a women look sophisticated. Men like women in boots….

    BTW, I like your dog!