Riding boots came into style for everyday wear a few years ago and seem to be here to stay! And by riding boots I mean basically any knee-high boot with a slight heel, the occasional buckle, strap or button, a zipper and with a slightly more casual flare. There are tons of riding boot options available and at this time of year you can probably get a good deal on a pair since stores are clearing out their fall and winter items to make way for sandals and swimsuits. But don’t get me started on that rant.
Love these riding boots
Source Source Source
Anyway, due to the overwhelming number of options at multiple price points it can be difficult to narrow down a pair that will be both functional and flattering. Sure, it’s easy to find ways to wear riding boots, but how do you know what criteria to consider when purchasing a pair?
Here ten suggestions you can use when looking for the perfect pair:
1. Make sure the heel isn’t too high or chunky. That will help them last through lots of seasons & styles.
Good Not Good
2. An almond or more pointed toe is better than a completely round toe as these shapes will help elongate your leg. But don’t go too pointy! That’s a different kind of boot altogether.
Round Almond Pointy
3. They should hit you just above the widest part of your calf or 2-4 inches below your knee. If they are too short they can make you look stumpy.
Same jeans, different boots
4. Real leather or faux leather is your choice depending on your feelings, but I will say that real leather ones will last for years and years and can be repaired and polished whereas faux leather will fall apart eventually and cannot be polished or repaired as easily. Also, I have found it difficult to buy faux leather brown riding boots that don’t look cheap. But, if that’s not your priority then that’s okay, too.
5. Measure your calves! And note the shaft circumference on the boots. You don’t want them too tight or they’ll be uncomfortable and you’ll never be able to tuck pants into them. Note: the calf circumference noted on most online shoe stores is measured from a size 7 or 8. The larger the shoe size typically the larger the calf width as well. If you’re right on the edge of the stated calf circumference but your shoe size is larger than the one listed as the standard then I would suggest going ahead and ordering them. Zappos has free return shipping so it’s easy to send back anything that doesn’t work.
6. I personally prefer to avoid anything that has a strap at the ankle as I think these can make you look sawed off at the ankles. Some people don’t minds this, though. Try on a pair that have an ankle strap and see how you feel when you look in the mirror.
Source Source
7. The fewer the embellishments the classier the boots look. Simpler boots also tend to outlast trends.
Classy Trendy
8. Brown boots or black boots? Personally, I wear my brown riding boots WAY more often than I wear my black riding boots. If you’re okay with mixing brown and black you can always pair your brown boots with black pants. But, really, it just comes down to personal preference. Sometimes it’s easier to make black riding boots look classier for the office and brown more casual, but you can make outfits with either.
Original post Original post
Similar outfits, different boots
9. Let’s be honest about price. Nice riding boots that last will not be cheap. $100 seems to be the lowest price you can expect to pay for a new pair unless you find a great deal in the clearance section at DSW or have some killer coupons. Both of my pairs cost me just under $100 and both are from DSW. Leather riding boot can cost upwards of $700 to $1000 or more. I certainly don’t think you have to spend that much, though! $100 to $150 should get you a great pair that will last you season after season.
10. Finally, think about your lifestyle and where you plan to wear them. Are you mostly casual? Then you might be able to spring for a pair with more flair. Do you get tired of your clothes and shoes and want to replace them every season? Then why not get something trendy. But if you want to wear them to a more business casual office then you’ll probably have to stick with a more traditional pair.
Thoughts? What did I forget? Do you already own riding boots? If you do, what did you take into consideration when you bought them?
0
Nothing is classier to me than tweed and a pencil skirt.
A reader recently contacted me and asked for help with a pair of ankle boots she just bought.
Right now I’m pretty happy with my closet. But even so there are days when I stand there and stare at all the hangers and think, “I wish I had….”
I’ve had all of these clothing pieces in my closet for a long time. I keep wavering on whether or not to keep the cardigan and then it keeps staying. 
Pairing the fancy sequined skirt with a neutral colored cardigan and nude heels helps keep it from being too bling-y or overwhelming.
