Casual Chic Outfit Basics | Riding Boots

Welcome back for the second post of my new series Casual Chic Outfit Basics.  Last week, I featured the first outfit basic, dark wash skinny jeans and this week we’re talking riding boots.

If you’ve been following my Daily Style Diary posts, you’ve probably already noticed that, other than dark wash skinny jeans, my other daily outfit essential this time of year is riding boots.  I wear a pair almost every day.

I’m normally not one to advocate for spending a lot of money on something.  But I have an exception when it comes to a few investment items and riding boots are one of them.  “Good” to me means quality, not necessarily name brand.  Don’t get me wrong though, a lot of times designer brands do equal good quality.  A brand name just shouldn’t be the main criteria.

Good also means real leather.  There are a lot of faux leather riding boots out there.  If you have a pair, it’s time to upgrade!

If you’ve been around here for long, you know I wear my Frye riding boots, like ALL the time.  From the time the weather cools down in early October until it warms back up in late April, they are in constant rotation.  Here are some ways I’ve paired them this fall and winter.

Frye Riding Boots OutfitsI can honestly say there has never been a piece of footwear I’ve loved more than these boots.  I’d marry them if I could (sorry Craig!).  They’re just that good – such high quality, a classic design that will never go out of style and the cognac color is drop dead gorgeous.  Plus they go with almost everything I own.

BUT they’re expensive.

As a matter of fact, they’re the priciest pair of shoes I’ve owned.  But also worth every penny.  Let’s do a little cost per wear breakdown, shall we?  On average, I wear them 2-3 times per week in the cooler months.  Take that times five months per year and divide by the purchase price and they are about $3 per wear (for the two years I’ve had them).  I’ll definitely be wearing them for a few more years so that number is just going to keep coming down.  Compare that to a pair of $50 heels I’ve only worn five times in two years and they are almost $10 per wear.  On a cost per wear basis, my Frye’s have been way more economical than a lot of the shoes I own.

My boots are the Frye Melissa Button Boot.  If you search for highest rated boots, they are right there on top for a reason – 583 reviews and 5 stars!  They come in nine different leather colors.  The cognac just happens to be my favorite.

[Frye Melissa Button Boot]

I understand that you might not be ready to buy the budget buster, though.  It took me a long time to pull the trigger.  That’s why I was so excited to find these similar looking boots, for a fraction of the price and they’re real leather.  They don’t have a lot of reviews, but the ones they have are really good.  They earned high marks for comfort.

Frye Knock Off Cheap[Rieker Riding Boots]

And now for some outfit inspiration…


Cognac Riding Boots Outfits[1/2/3/4]

I realize that Frye doesn’t make the only cognac riding boot around.  There are plenty of other gorgeous options out there at every price point.  Here are a few higher rated pairs.


Another beautiful Frye boot with a small heel.  These are on sale right now for 40% off!

[Frye Jane Strappy Boot]

MID-RANGE ($100-$200)

These boots are just the perfect color of cognac and have a nice distressing on the front.  They’re also a great alternative to the Frye at about half the price.

[Sam Edelman ‘Penny’ Boots]

It’s rare to find a boot this gorgeous at this price point.  These boots are normally $200 but on sale for 25% off.  Hurry if you want them, all sizes are in stock now!  I’m really going to have to exercise some self control because I want these pretties in my closet.

[Corso Como ‘Stirrup’ Boot]

UNDER $100

Yes!  There is a great leather option at this price point.

[Lucky Brand ‘Andria’]


While I was looking up cognac riding boots outfits, I stumbled across this little gem.  Let’s just call it the perfect casual Valentine’s outfit!

Valentines Day Outfit[Via]

The red and white gingham, lightweight v-neck sweater, white skinny jeans, statement necklace and cognac boots scream casual, chic Valentine’s Day.  Don’t you think so?


Valentines Day Casual Outfit Collage[Necklace/Sweater/Gingham Shirt/Jeans/Boots/Watch]


Two Tone Riding Boots Outfits[1/2/3]

Two tone boots are HUGE this winter.  I’m usually not one to recommend investing in a trend but this one is here to stay for awhile.

HIGH END ($250+)

This pair is the budget buster, but oh my!  Are they ever pretty.

[Frye Melissa Logo]

The original riding boot – Ariat.

[Ariat ‘York’ Boots]

MID-RANGE ($150)

[Donald J. Pliner ‘Prize’]

[Tommy Hilfiger ‘Delvin’]


Black Riding Boots Collage[1/2]

You just can’t go wrong with a classic black riding boot and I found some bargains in this category.

UNDER $150

The lines on this boot are just perfect and it’s 50% off!

[Louise et Cie ‘Verrah’ Boots]

This boot is also on sale and comes in four different color combos in all leather or leather and suede (as shown).

[Anne Klein ‘Ciji’ Boots]


Taupe Suede Boots Black and CreamMy second most favorite pair of footwear is my taupe suede riding boots.  They’re such a pretty neutral and go with so many things.  I swap them in when it’s time to give my Frye’s a break.

UNDER $150

The color and style of this boot is very similar to mine.  They’re also 30% off!

[Seychelles ‘Nothing to Hide’]

Be sure to stop by on Monday for a recap of last week’s Daily Style Diary!

Getting my pretty on with The Pleated Poppy, Fashion Friday.