February 7, 2014 - Casual Chic Outfit Basics, Easy Outfits, Style

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 Outfits I 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 Zappos.com 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 Cream My 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.

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  • Great post, I want a pair of Frye boots so badly I think that will be my pick when I’m ready to update my Cole Haan pair.

  • I am in need of a new pair of tall boots for next fall. You have convinced me to invest in a pair of Frye boots! Love these! Susan

  • That Valentine’s Day look is sooooooooooooooooooo cute! LOVE the gingham, the sparkly necklace, the white jeans, and the boots! Seriously LOVE it!

  • I really want 2 toned riding boots. I love all your looks especially the vday inspired one!


  • I do have Frye Melissa boots in black. Yes they are pricey but I do wear them all the time. I am saving for a cognac pair now. The good thing is that these boots will last literally forever!

  • Yes riding boots are SO important! i have so many of them! lol 🙂 im def addicted but you cant go wrong with them

  • I have a couple pairs of Frye boots. I love them, but I love your cost/wear analysis better! I wait until the Nordstrom anniversary sale and pounce on them when they go on sale.

  • I have two pairs of frye boots and they are worth every penny. Plus I find the cheaper versions don’t accommodate larger calves but the Fryes generally do. And they are real leather lining (cheaper versions usually are not) which means they will stretch with you!

  • I was super lucky to find my Fryes 1/2 off at Zappos a few years ago – I snatched them up in a New York minute! I will never get rid of them, they are classics. 😀

    The Valentine outfit is cuteness without being over the top with the hearts. LOVE.

  • For the things we care about (like riding boots or motorcycle gear), quality matters and we should never apologize for getting the best. Price is irrelevant. I spend ridiculous amounts of money on motorcycle stuff. These boots are terrific.

  • I have so many boots, but love my cognac ones the most! It really is worth it to spend more for quality with boots you are going to wear so much. Love all these outfit ideas, too!

  • Saxon

    I have 3 pair of boots and after reading this post I want 3 more! I have the Sam Edelman Penny boots and LOVE them. They run a tad narrow but because they are real leather, they are forming to my foot nicely as I wear them. I ADORE the two toned boots and would love to have a pair of them. I’d like a pair of black, too. And after this post, I want taupe suede boots! With this below average winter, I have had a pair of boots warming my feet almost daily. I’m hoping the boot trend will never go away. Well, at least it won’t for me. I love them too much. 🙂

  • I LOVE LOVE the taupe…I just had to replace my black tall boots so I am torn with spring around the corner…another pair or spring stuff. Those make it hard to decide!

    Patrice @ http://dittothatstyle.blogspot.com/

  • Margaret Schrader

    Again, I am loving your blog!!! The outfit posts are my fav!! Keep going in this great new direction!!!! :))

  • Totally agree. Riding boots are a great investment!

  • I really love all these boots too, but I don’t know how they look on girls with pretty wide hips like myself…any thoughts on how to stay on trend and still be figure flattering?

  • So many lovely boots! I have a pair of Frye boots and love them… really great quality, comfortable, and classic- definitely worth the splurge!

  • This is actually really helpful, because I’m in the market for a new pair of boots… but black ones. I love the Frye in black!!

  • Alison, I so agree about a good pair of boots ( or three!)
    They are a great investment if they are comfortable and you wear them for years.
    I do love your choices, and I love the bag, in that photo of you in the lighter colored boots, gorgeous!
    XX, Elle

  • Riding boots are awesome, and if you get a good pair, they’re definitely a worthwhile investment. I tried a couple pairs on the cheap and wore them so much they were destroyed by the end of the season I’d bought them! I definitely want to invest in a pair of Frye boots, but I want to wait until I can try them on in person. I’m a former sprinter and power lifter, so my calves are not small.

  • Jay

    I love your post. I took my hubby boot shopping with me & he picked out a pair I didn’t care for but I bought them cuz he really liked them. I wore them a couple of times last spring and none last fall/winter. Lesson learned, I will never take him shoe shopping again : )

  • Frye boots are so pretty! I love your Valentines outfit!

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