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One outfit, two ways: OTK boots from desk to dinner

Sep 29, 2017

over the knee boots outfits for the office

Faux leather skirt: Topshop (less than $50!), Suede OTK boots: Stuart Weitzman (splurge!) but these are my favorite budget-friendly OTK boots and I LOVE them. (Also come in grey!) They’re also waterproof! Convertible Sweater: (both cowl neck AND off the shoulder!): Nordstrom (comes in SOO many colors and is the softest thing you’ve ever felt!) Work Tote: Madewell Transport tote – also comes in plain black, and I really want the black version with tan handles, too! Leopard Clutch: B.P. – it’s only $49! (also, have you seen this leopard crossbody for $99!?)

Is it just me, or is it widely known that Fall is everyone’s favorite time of year to get dressed? It’s not too hot, not too cold…(okay, other than April 25th, which as we all know, is the perfect date! :-P)

But really. I’m ready for boot weather!

On the flip side though, for those who work in business casual environments, Fall can be a little bit more of a challenge! I mean, in summer, all you have to do is throw on a dress and flats. But Fall requires more layers. And sometimes layers and add, you know, more complications.

One tricky situation in particular–you love your OTK boots, but you don’t know how to make them work for the office in a way that is, you know, appropriate?

Until, TODAY. My friends.

Topshop leather pencil skirt

To set the scene: I’m in my living room (because that’s where our full length mirror is, so sadly for Neal, this space often gets turned into my closet when I’m prepping for photo shoots) amidst of what looks like the aftermath of an atomic clothing bomb.

“I’m playing around trying to figure out a way to make my OTK boots work for the office.”

Neal snorts and eyes me suspiciously, giving me the, “don’t you know there is no WAY you are going to make those boots look “conservative” look, before walking back into his man lair.

About 10 minutes later, I bounded into his home office and just stood there proudly, waiting for him to look up from his desk.


(Guys, if Neal approves, you know it’s a good outfit.)

Over The Knee Boots Outfits: How to wear OTK boots to the office

So, let’s jump into these pieces, and most importantly, why this outfit works, yes?

First of all, you can get all of them at Nordstrom, which is one of my favorite places to shop for really versatile wardrobe staples. If you’re looking for a few key, quality pieces that you can wear to work, to date night, out with the girls, and to brunch, I think their selection and range of price points is truly unparalleled.

Now that you know where to get your key wardrobe staples, on to the styling tips! 😉

Over the knee boots outfits for the office:

First, let’s discuss the OTK boots themselves. I own two pairs of flat OTK boots. My first OTK purchase was the Blondo Olivia Boots, and I went through a LOT of trial and error to find them. I have small calves, and no other OTK boots that I found (aside from the Stuart Weitzman Lowlands) fit me properly. They are a fantastic price point, and best of all, they’re waterproof. Unlike the Lowlands, they do not tie in the back, but have elastic in the back so they really do hug your calves–this is great for everyone, from small calves, to larger calves and everything in between.

Then, Neal surprised me with the Lowlands for Christmas, which are now my go-to boots, because–obviously. They are phenomenal and hands down are my favorite pair of boots I will ever own. However, I still do wear my Blondo Olivia boots when its bad weather out and I don’t want to expose my Lowland boots to snow or rain.

Both pairs run true to size, and I love them both so much for different reasons. Deciding which is right for you really comes down to price point, but I hope this makes your shopping a bit easier!

Faux Leather Pencil Skirt

I was worried this leather pencil skirt would be too long to pull off with OTK boots. (Personally I like when there is a sliver of leg showing, otherwise, I feel like it looks too matronly) but it turns out, it’s the perfect length! It’s not too short to wear to the office, but it’s also not so long that I wouldn’t wear it out at night. It’s not too tight either, which is obviously the other concern with making it 9-5 appropriate. The best part is that it’s under $50 as well. (Sizing tip: Topshop runs small, so make sure to order the size in parenthesis for the best fit. Another reason I love Nordstrom–they always have the most accurate sizing tips!)

Versatile Sweater

Desk to dinner staples for fall: the cowl neck sweater

This convertible sweater is EVERYTHING you guys. It’s cowl neck, which is great, but even better–it’s off the shoulder, too! It’s actually tunic length, but easy to tuck in as well. I will definitely be wearing this on my next airplane with leggings and sneakers. Hint: It’s also going to be featured in a new series coming up where I show you how to style it even more ways. Get excited! It’s so incredibly soft, and it comes in so many colors. I think I may order it in the green and burgundy as well!

Roomy Work Tote

This is no surprise, you see this tote bag on the blog almost weekly. It’s an amazing work bag and is so roomy. It fits both my laptop and my camera at the same time when I travel, and whenever readers ask for my reccos regarding work totes, I always send them to this one! I really love the black and brown version too, which might be better if you tend to wear a lot of black to work.

Why this look works

Whenever you wear OTK boots with a skirt, you want to make sure that you’re balancing them out on top, especially if you’re going to work. If you show too much skin when wearing them, you can often look, ehrm, “like a floozie” as my mom might say.

The reason this look works well is because the skirt length is long enough to still be office conservative, but short enough to still show off a little bit of leg without being inappropriate. Additionally, the BIG reason this works is because the boots are flat. If you’re going to splurge on OTK boots, I always recommend flat ones, just because, when you add height, again, it’s much easier to, you know…as Lynn would say.

The fact that the sweater also has a cowl neck works nicely to add some volume and balance up on top. It’s basically like having a built-in scarf!

Over the knee boots outfits–how to make them office appropriate

Over the knee boots outfits for date night:

Now, suppose you’re going straight from work to a date–you don’t have time to go home and change, and you don’t want to look like you just came from the office.

What do you do?

Just two little steps, and you’re set!

Pull your sweater off the shoulder

Over the knee boots outfits for date night


All you have to do to take it from desk to dinner is pull down the shoulders!

Swap your work bag for a clutch

Off the shoulder fall sweater

This leopard clutch has already proved to be so versatile and one that I will wear all year round. I purchased it in the summer but it’s also great to add a pop of pattern and interest to fall outfits!

Switch up your hair and lip color

This one honestly isn’t even required, just a bonus! At the end of the day, my hair has usually fallen. It doesn’t look as great as it did in the morning. So, I often opt for a ponytail if I don’t have time for touch-ups. Fun fact: This is Neal’s favorite way that I wear my hair! I usually pull it into a high ponytail upside down, and then pull a few pieces up on the top of my head to give it some messy volume. For lips, it’s no secret that I love red. MAC has some of my favorite formulas–”MAC Red” is a classic hue, and I love “Lady Danger” for a more orange pop!

Over the knee boots outfits for going out How to wear an off the shoulder sweater this fall

How would you wear this outfit to make it your own? 

P.S. more over the knee boots outfits here and here!

This post brought to you by Nordstrom, one of my favorite retailers

Photos by Cassandra Eldridge 

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