Wear It Now and Later: Ankle Boots

You know what’s weird?  I keep getting asked if booties are going out of style soon because people want to buy a pair and they’re not sure if they should.

I find it weird because besides the fact that it has happened multiple times, to me, booties are a closet staple!  I never worry about them going out of style.  Though they’ve been getting more attention and hype lately, I’ve always seen them as a closet staple.  I’ve been wearing them for 5 years, and I started because I saw them on other people years before that.  I didn’t even know they were trending until I got several questions about them this month.  To me, they have been one of my go-to shoes for the fall for years and they will continue to be, even when/if the current hype around them dies down.  If you too have been wondering if ankle boots will last in your closet, my answer is an emphatic YES!  (As long as you stick to a classic silhouette that doesn’t have super trendy details, of course!)

One huge reason I love ankle boots is because they are a great alternative to riding boots when you want to dress like it’s fall but the temp is still too warm.  One circumstance would be the transition from summer to fall, when you’re feeling the fall style itch but it’s still warm.  Another circumstance would be for anyone who lives in a warmer climate, like me, where it hardly gets cold.  Our falls and winters don’t warrant riding boots often, so ankle boots are the way to go.

I thought I’d provide a few outfit ideas for how to wear booties now and how to wear them once fall kicks in.  And I’m teaming up with Nordstrom again to do it!  Hopefully this will help you get more use out of them instead of waiting until fall and winter to wear them!

There were several great pairs of booties during the Nordstrom Anniversary Sale, but above is the pair I ultimately kept (found HERE).  Since last year I’d been looking for three things in a new pair of booties:

  • 1) Lighter color.  I have black, brown, and a greyish taupe, but I wanted a lighter pair.  This was the exact color I was looking for!
  • 2) Nearly flat heel so I could walk all day in them.  The description says this heel is 2″ but it feels lower than that, and that’s what’s important.  I wanted an everyday pair that I could walk at length in.  Honestly, that part is to still be tested because I won’t know until I actually walk all day in them.  Haven’t gotten there yet.  Based on limited wear compared to all the other booties I tried, these seemed to have the best chance.  
  • 3) Lower shaft aka doesn’t come up too high.  I prefer a lower shaft because of the shape of my calves and legs and how some booties with a higher shaft shorten my leg line due to having to roll the jeans up higher.  This pair was the lowest of all I tried and hit exactly where I wanted it to.  (See last year’s post on How to Choose the Right Pair of Ankle Boots HERE!)
I can’t believe I finallyyyyyy found a pair that met all these things!  YAAASSSS!  In terms of comfort, I’d consider them normal/neutral.  Not uncomfortable at all, but I’ll put insoles in them for more cushioning.  Otherwise, the lower heel should make it easier to walk in, and the material doesn’t rub my ankles or feet poorly.  I’m normally size 8.5/9 and wearing 9.

They are almost sold out in this color, but a very similar pair by the same brand is HERE.  I tried them, and if I remember correctly they are possibly more comfortable than the pair I ended up keeping.  I didn’t choose these because they came up slightly too high on my ankle, but if you don’t need to be picky about that those are great!

Here are some looks!  

ankle boots + striped dress outfit
ankle boots + striped dress outfit
ankle boots + striped dress outfit
ankle boots + striped dress outfit

Outfit #1 – With Dresses or Skirts
This is one of my favorite ways to wear ankle boots when it’s still warm.  Since it’s still summer weather here, I’ve worn this outfit in extreme heat, but with sandals instead of booties.  I’ve also worn it with booties during the cooler evenings.  Besides the practicality of warmer feet keeping me warmer, trading the sandals for ankle boots instantly turns it into fall style even if the weather is still warm.  Kinda fun how much a pair of shoes can change an outfit, isn’t it?

If it’s a little cooler you can add a layer, like a blazer, denim jacket, vest, leather jacket, or whatever.  This is that super duper comfy knit blazer from the NSale.  It feels like a thin sweatshirt but looks less sloppy, even when paired with this loose t-shirt dress.  I’m normally size S/M and wearing S.  Comes in 5 colors!

Shop for the Look:
Dress: Target
Blazer: Nordstrom (exact–wearing S)
Shoes: Nordstrom (exact)
Necklace: Nordstrom
Bag: Nordstrom (exact)

printed top + utility vest + jeans + ankle boots - cute fall outfit
utility vest outfit
utility vest outfit
Outfit #2 – Short Sleeves and Light Layers
Basically, take any jeans + tee or blouse outfit and give it more character by adding ankle boots.  If it’s not too hot, add a vest too!  You could wear ballet flats or sneakers with this outfit, but just as we talked about in the dress outfit above, the ankle boots make it feel like fall.  I haven’t actually worn this yet since it’s been too hot for jeans, but I loooove this outfit and can’t wait!

If you missed it, see this top remixed 3 ways HERE.  
Also, can I take a moment to rejoice finally, finally, finally having the right jeans that are skinny enough at the ankles on me and the right booties that have a low enough shaft to show some ankle while maintaining a streamline silhouette?  (Don’t know what I’m talking about?  Check out that post on wearing ankle boots with jeans HERE.)

Shop for the Look:
Top: Nordstrom (exact–wearing S)
Vest: Old Navy (similarsimilar)
Jeans: Nordstrom (exact)
Boots: Nordstrom (exact)
Bag: Nordstrom (exact)

fall outfit maroon cardigan
fall outfit with maroon cardigan
maroon cardigan + white top + jeans + booties
fall outfit with ankle boots
Outfit #3 – Long Sleeves and Thicker Layers
I’d wear this at the beginning of fall, and of course I’d wear thicker layers or add scarves as fall progresses.  But you still get the idea.  While you could wear riding boots with this, like I said earlier, ankle boots are an excellent alternative if it’s too warm for riding boots.  (On an externally processing note, looking at all these pictures just confirms how much I love the color of these boots! 😀 ) 
This cardigan sold out super fast during the NSale, but it’s restocked again in 5 colors!  It’s fairly soft, and though I’ve met softer thick cardigans what stands out to me about this is how light it is.  Usually the weight of thicker cardigans drags me down over time, but these feel lighter than my other cardigans like this so I’m hopeful!
Also, I got this top a year ago and it’s available and on sale again.  It’s actually a very long tunic length, but I’ve only worn it tucked in the front because it drapes so nicely for that.  And don’t mind the “dry clean” instructions.  I machine wash and air dry this and it’s been fine.  One of you told me you have a ton of these and machine wash and machine dry and they look new.  Comes in 8 colors HERE.  

Shop for the Look:
Top: Nordstrom (exact–wearing M)
Cardigan: Nordstrom (exact–wearing S)
Jeans: Nordstrom (exact)
Boots: Nordstrom (exact)
Bag: Nordstrom (exact)

Shopping Options
If you’re in the market for ankle boots, here’s some help!

the best pair of ankle boots
Links to Shop:
one  |  two  |  three  |  four  |  five
six  |  seven  |  eight  |  nine  |  ten
eleven  |  twelve  |  thirteen  |  fourteen  |  fifteen
I reallyyyy like the ankle boots I ended up with, but I know they might not work for everyone.  I sifted through Nordstrom’s selection of ankle boots and almost all of these have RAVING reviews by tons and tons of people.  Only a couple of them don’t have reviews because they’re brand new, and I didn’t even include others from Nordstrom that have mediocre reviews.

Second note, every single one of these comes in multiple colors.  Many of them come in 3-5 colors, while some even more than that!  As you browse, pay attention the shape and characteristics more than the color because it’s likely you can find a color you like with these.  For example, if you see a black one and go “Ehhh, I wasn’t looking for a black one,” it probably comes in taupe or cognac or tan too, so don’t rule it out.

I tried Option #3 (HERE) during the NSale and was amazed by how comfortable they are.  On initial wear, they felt more cushiony than the pair I ended up with.  The only reason I didn’t get them was because I knew I didn’t need them right now!  
Options 9 and 10 (HERE) are so cute!  I especially love the light wood heel for the black pair, as I think adding the lighter contrast softens the black more.  They are one of the pairs with only a few reviews, but still 5 stars!  (Almost all the rest of the boots have hundreds and hundreds of reviews with 4.5+ stars.)

Here are some past posts if you aren’t sure what to look for when ankle boot shopping!

More Ankle Boot Outfits
Lastly, for more inspiration here are ways I’ve worn my other ankle boots:
Good luck!

Created in partnership with Nordstrom

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