Comparing Ankle Boots: Which Should You Buy?

Advice on Which Ankle Boots to Buy

Lately I’ve shown a fair amount of ankle boots, and personally when I see bloggers talk about how much they love this, that, and everything else, I find myself going, “Yes, I know you love all of them, but which do you love MOST?”  And more importantly, “Which one should *I* buy???”  I thought it’d be helpful to write one post comparing the boots I’ve shown lately.

If you are looking for guidance on how to find the right ankle boot for you or are wondering what characteristics you should be looking for, check out both of these posts: 1) Choosing the Right Pair of Ankle Boots and 2) How to Wear Ankle Boots with Jeans and Dresses.

In a nutshell, if you don’t want to read those posts, how I personally evaluate boots is based on:

  • 1) Wanting boots with lower shafts or dips in the front to elongate my legs.  Other people can get away with any shape of ankle boot, but something about the shape of my calves or ankles makes many ankle boots look strange on me if they hit a certain area on my ankles.  They look like clunky elf shoes on me.  See HERE for picture comparisons of what I mean.
  • 2) Comfort.  How long or how much can I walk in these without wishing I had on different shoes?  Some days I need to do hours and hours of walking.  Some days I do little walking and can get away with less comfortable shoes.
  • 3) Color.  Do I need this color in my closet?
For sizing reference, I’m normally 8.5 or 9.  
If you made me choose to have only one pair of ankle boots in my closet, it’d probably be this pair or the pair below.  I got these during the Nordstrom Anniversary Sale, and while they’re not on sale anymore they got restocked and are available in most sizes.
Why I love it: 
  • Color.  This color is incredibly versatile.  Because I tend to wear darker colors in the fall I find many ankle boots that are a little darker, whether a darker taupe or tan/brown, can make my outfit feel dragged down when combined with darker colored clothes.  This is not always the case, but it often is.  This color not only goes with a lot of things, but it lightens up my outfits and makes them feel fresher.
  • Comfort + Low Heel.  It is not the most comfortable boot I’ll speak of today, but it is comfortable.  I put my favorite insoles in them like I do with most of my shoes (THESE, reviewed HERE), but also the material is sturdy without being stiff, the quality is good, and the heel is low and walkable.  Several of you have told me you bought them after seeing them here and find them really comfortable.  
  • Low Shaft.  In Choosing the Right Pair of Ankle Boots I illustrated why I prefer a boot with a lower shaft or a cutout in front.  It elongates my leg line.  Secondly, it makes the look cleaner.  Other boots that are slightly higher come up around my ankles and look very loose.  When that happens the boot can look too big on me, appearing clunky and kinda like elf shoes.  This is of course particular to your leg shape, but the shaft on this boot is low and creates a streamline look for me both with jeans and dresses.  That is SO HARD for me to find!
What I don’t love: Honestly, not much! 😀  Sometimes other booties look better with certain colors or dresses, but if this were the only pair of boots I was allowed to have in my closet, I would NOT be sad about that!

They used to only be available in this color and black, but are now available in 5 colors!  Find them HERE.

Shop Outfit #1:
Dress: Old Navy (exact)
Scarf: c/o ModCloth (exact)
Boots: Nordstrom (exact)

Shop Outfit #2:
Top: Nordstrom (exact in other prints)
Vest: Old Navy (similar)
Jeans: Nordstrom (exactsimilar)
Boots: Nordstrom (exact)

Unfortunately these are several years old and not available anymore.  I get asked all the time for similar options, but I have been hard pressed to find them.  I think this style isn’t really “in” anymore and therefore not widely available like it was the year I bought them.  I don’t care–they are the most flattering for my leg shape so I really don’t care if they’re in!  
Why I love it:
  • Shape + Cutout.  I talk more about it as the ultimate example for me in Choosing the Right Pair of Ankle Boots, so head there if you want to know why.  They look good with all skirts and dresses, and I don’t have to roll my jeans up as much to show a little ankle thanks to the cutout, which also elongates my leg.
  • Color.  I’ve had these for several years and I’ve found that these work really well for many outfits, but they are the biggest winners for outfits that no other color boot I own looks right with–including the lighter colored pair above.
What I don’t love: I both appreciate and don’t appreciate the heel.  The heel adds length and elongates blah blah blah, but I skip over these if I’ll be out walking all day.  They’re not even uncomfortable, but I just can’t walk miles in these or can’t walk as quickly as I could with a lower or heel like the pair above.  Sometimes you just NEED a flat boot.

I wear these when: The color of the previous pair of boots doesn’t work, a skirt or dress looks better with heeled boots and the dip in the front, or when I don’t need to do tons of walking or standing.

Shop for the Look:
Top: J.Crew Factory (exact–wearing S)
Vest: Old Navy (exact–wearing S)
Jeans: Nordstrom (exactsimilar)
Bag: Nordstrom (exact, similar)
Watch: c/o Daniel Wellington (exact)

These are also several years old and not available anymore.  I got these shortly after I got the pair above.  They don’t feel as good as the pair above, but they do the trick, they’re flattering, and they’re my only pair of black booties.

I wear these when: I need a black boot.  Pretty simple.

Shop for Outfit #1:
Top: Nordstrom
Cardigan: Nordstrom (similar)
Jeans: Nordstrom (exact)
Bag: c/o Sole Society
Boots: Kohl’s
Watch: c/o Daniel Wellington (exact)

Shop for Outfit #2:
Sweater: Old Navy (exact)
Jeans: Nordstrom (similar)
Scarf: Zara (similar)
Boots: Kohl’s
Bag: Nordstrom (exactsimilar)
Watch: c/o Daniel Wellington (exact)

I only got these recently and it’s been quite warm lately, so I haven’t had much opportunity to wear them.  My real test with any shoe is running errands for hours and seeing if they hurt or slow me down in any way, and I have only sat or stood for long periods in these shoes so far.  That said, here are my thoughts.

  • Price!  These are under $40.  I know not everyone wants to spend $80 or $100+ on ankle boots.  I’ve already said my reasons in recent posts about why I buy more expensive boots now, but it doesn’t mean I don’t still seek to find the same quality at a lower price point.  These are good for lower priced boots.  They don’t seem like they’ll do that annoying creasing thing at the toe like I’ve griped about before.  (Only time will tell, though.)  I don’t think they look like $100 boots, but they are still better than other boots in their price range.  
  • Style – Heel + Color: The shoe is really cute.  The heel makes it easier for me to wear with jeans, extending my leg line.  The zippers add a fun element.  And the color–I like that it’s a medium tan as opposed to darker.  Like I said, darker colored browns or taupes tend to muddy up my outfits.  

What I don’t love:
As I said earlier, while they’re good for the price, I feel a noticeable difference in quality and how the material feels between these and my more expensive pairs.  That’s not true of all less expensive boots, but I do feel the difference with these.  Also, any heel is both a plus and a minus as I said with previous pairs.

I’d wear these when: I need a brown boot to wear with skirts or dresses, when I need to wear a brown boot and don’t have to do a ton of walking or standing, or when I’m going to do activities in dirt or rocky areas and don’t want to worry about scuffing up more expensive boots.

Shop for the Look:
Top: c/o ModCloth (exact)
Jeans: Nordstrom (exactsimilar)
Bag: c/o Lily Jade (exact)
Boots: Target (exact)

These are the most expensive ankle boots I own, but you can definitely feel the quality.  Recently another reader told me they bought a pair of Clarks booties 6 years ago and they’re still going strong!  These are almost the most comfortable boots I own.
  • Quality.  Stated above.
  • Incredibly comfortable.  These are super comfortable, from the low heel to the cushioned footbed to the sooooffffft buttery leather.
What I wish were different: The height of the shaft isn’t as low as I prefer, and the boot looks loose around my ankle.  I don’t think these would work with dresses or skirts for me.

I’d wear these when: I need a brown boot and need to do lots of walking.  And I would have to wear them with jeans.  If they looked good with skirts and dresses on me (i.e. had a lower shaft or a dip in the front), I’d probably get rid of the pair above and always wear these.

Shop for the Look:
Tee: Nordstrom (exact)
Cardigan: Old Navy (similar)
Jeans: Nordstrom (exactsimilar)
Shoes: c/o Zappos (exact)
Bag: Nordstrom (exactsimilar)
Necklace: c/o Dear Mushka (exact)

I love all the same things about them as I said about the pair above: incredibly comfortable and well made.  However, these are slightly heavier than the pair above, and because I walk pretty fast I don’t love walking in these because of their weight.  Unfortunately, that’s the main reason I hardly wear them.

I wear these: Almost hardly ever, sadly.  As good as they are, I’d choose any of the other pair of boots above.  I might choose them if I needed a brownish gray boot with some more character–so basically mostly for style.

Shop for the Look:
Top: c/o Gray Monroe
Jeans: LOFT (similar)
Scarf: c/o Ooh Baby Infinity
Bag: Nordstrom (exactsimilar)
Boots: c/o Zappos (similar)

The color of this pair is similar to the Franco Sarto pair I talked about.  They are a lower price point, and you can feel the difference in quality, but I think they are decent.  The material is a little stiff compared to all the other boots I talked about, but they are still wearable.  The heel makes it easier to wear with jeans or skirts, and I don’t need to be as mindful of how high the shaft as a result.

Personally, because I already own the Franco Sarto pair and the Target cutout boot (first 2 pairs) I felt I would always choose those pairs over these.  Instead, I mailed them to my friend who has been looking for her first pair of ankle boots!

In a nutshell, I prefer more expensive pairs over this pair because of the better material, but if you need a taupe pair under $50, look into these.

Shop for the Look:
Top: c/o ModCloth (exact)
Jeans: Nordstrom (exactsimilar)
Bag: Nordstrom (exact)
Scarf: c/o ModCloth (exact)
Shoes: c/o ModCloth (exact)


I’ve tried several peep toe booties/mules, but they usually came up too high on my ankles.  Not only do they look bad with my calves, they are uncomfortable when too high and cut into my ankles!  These actually worked, and I’m so glad!  They are on the less expensive side but feel pretty decent.  I’ve only worn them a couple of times so far, but already they are creasing–in a different place than other ankle boots.  Other ankle boots crease at the toe, but these are creasing where my ankle bends.  You can kind of see it in the photo on the left on my right foot that’s crossed on front.

In terms of comfort, I wouldn’t say they feel “AMAZINGGGG” or anything like that, but on the other hand, the shoe never bothers me.  The thick heel is very easy to walk in.  Overall, I actually really, really like this pair and am happy with them given the price.

I’d wear these when: Sometimes a fully closed toed boot looks kinda weird.  I don’t know, I wish I had a picture comparison to illustrate that.  But, that’s when I’d opt for a peep toe bootie.  Obviously also not when it’s raining or snowing (which is seldom a problem where I live!)

Shop for the Look:
Top: c/o ModCloth (exact)
Jeans: Nordstrom (exactsimilar)
Shoes: c/o ModCloth (exact)
Bag: Nordstrom (exact)

Those are all the ankle boots currently in my closet!  Here are a few more below.  The top row is under $40 and the rest under $100 thanks to a current sale.  I have no personal experience with these, though for expensive ones I tried to choose ones with good reviews.  I have tried #8 and they are surprisingly comfortable.  Most of them come in a variety of colors, so if you like the style, see if they have a color you like.  Good luck finding a pair that works for you!

Links to Shop:
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