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How to wear ankle boots to the office

How to wear ankle boots to work

Blazer: c/o Everlane (runs TTS. Comes in navy and green too!) c/o Pants: Everlane Work Pants (here I’m wearing the ankle length but they come in full length as well! They are super stretchy but substantial! I think they’re pretty true to size!) This outfit would also look just as cute if you swapped the work pants for jeans (Their “Cheeky Straight” jeans are my latest fave! Run TTS!)  c/o Ankle boots: Everlane Day Boots – run TTS and come in lot’s of colors! If you are also looking for loafers, I’m in LOVE with their Modern loafers (order 1/2 size up! They run snug!) This outfit would also look super cute with loafers! c/o Silk camisole: Everlane (runs TTS) I also LOVE their silk button downs (also run TTS!) c/o Messenger bag: Everlane Form Bag (the strap is adjustable so it can be a cross-body or a tote!) c/o

Happy Monday friends!

How was the weekend? I hope you had some time to wind down and relax! It’s been “go go go!” since I got back from Portugal, but fun despite the madness!

This weekend Neal’s little brother, Brendan, starred as Young Simba in the Lion King! He was AMAZING and it was so fun getting to watch him on stage–they even got a write-up in the Chicago Tribune!! (Brendan is in TWO photos! ??He’s a celeb!) It was definitely the highlight of the weekend. We’ve ALL been practicing “I just can’t wait to be King” for over a year now so seeing it all pay off was amazing! So proud of him!

I hope your weekend was just as much fun 🙂

Today’s post, I know, is going to be a hit for my 9-5 girls. I get a LOT of questions about ankle boots–specifically how you can wear them to work and make them look business casual–today, I have your solution ?

[one-half-first]Ankle boots: Everlane Day Boots [/one-half-first][one-half]

Ankle boots: Everlane Day Boots 

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How to wear ankle boots to the office:

My tip: Get the Everlane Day Boot. And it is MAG-I-CAL.

Why I’m obsessed with these boots: They are the most comfortable block heel boots you will ever put on your feet. Period, the end. You know my obsession with Everlane’s Day Heels–yep, these are the boot form! (Ahhh no WONDER they’re so comfy!) They are so comfortable, in fact, that I wore them for two days straight in Portugal, walking on cobblestone streets for 12 hours on end–and no problems–like, at all. My feet were not aching at the end of the day, and I never got any blisters.

Sizing: They run true to size and come in lot’s of colors, too!

Shop more colors of The Day Boot: 


Why they work so well for the office: These boots in particular are much sleeker than a lot of other ankle boots, which can tend to be a bit chunky. Additionally, the combination of the rich color and leather make them easier to dress up than say, a suede boot, which is really always going to feel casual no matter what you pair it with. The way they’re cut also makes them more polished–they’re a bit higher, whereas some ankle boots that are cut lower on the ankle can be chunkier, which, you guessed it–is just harder to dress up. I also like how they don’t have a pointy toe, but also don’t have that basic perfectly round look that can make your feet look wider at tip.

How to wear ankle boots with work pants:

Everlane’s “work pants” in particular do work very well here, because you want a pant that hits above the ankle if the pants aren’t super skinny. Somewhere between a straight leg pant and skinnies. Here’s why: If you have a pant with a straighter leg that hits right below where the boot begins–it makes you look like you have giant cankles ?

Now, on the flip-side, say you were wearing a skinny pant that was very tight at the ankles–that would be okay if they went all the way down to tuck into your boots, because that gives you a “defined” ankle–if that makes sense. Personally though, I really love the look of a cropped pant with ankle boots!

I love these pants for work for a couple of reasons–they feel like leggings but look like cute trousers–but they don’t look so much like “work” pants that you wouldn’t want to wear them on the weekend with a cute pair of sneakers. The material is also super substantial and doesn’t wrinkle easily, so if you want to wear them to walk to work with snow boots or rain boots, you can easily do that and they won’t come out of your boots looking like a hot mess. (Ah, the woes of a commuter.)

Other pants I love: Their go-weave “easy pants” also look ADORABLE with these boots, and are another pair of Everlane pants that are perfect for the office, but comfortable and cute enough that you’ll want to wear them outside of your work environment, too!

Shop favorite Everlane Work Pants: 


What if your ankles get cold?

 You can totally wear socks! Just make sure they’re appropriate for the occasion! For example–for work, you’d want to wear a thin, dressier sock, vs with jeans you could definitely getting away with a more casual, chunky sock. As opposed to a thicker winter sock for casual outfits. If I were to wear socks with this look, for example, I would go with a thinner, charcoal colored sock!

Now, what about the rest of this look?

Sure, the boots are the unsung hero of this work outfit, but what about the blazer, camisole, and bag? ?Let’s talk about those next!

How to wear ankle boots to work

The Blazer:

I am ALL for the oversized blazer trend right now, but there’s something so classic about a tailored blazer that I’m always drawn to. I think it’s more flattering on all body types and it can be a lot less daunting to try out a fitted blazer than a more trendy oversized version! This particular blazer comes in navy and this brown/green color but I’m clearly a sucker for houndstooth tweed ?You know I’m always harping on adding a pattern and/or textural element to all outfits, and this definitely serves that purpose! I feel like it gives a little nod to British style as well, which I love!

The Silk Camisole:

Duh–slinky camisoles aren’t a new staple around this blog–but know what is? Everlane’s clean silk collection!! ??These camis are drop dead gorgeous–made of the softest silk–it’s stunning on its own in warmer temps, and the perfect layering piece for cooler temperatures–from work to going out!

All of their silk pieces are made in a Silver LEED certified factory in Nanchong China. Everlane goes above and beyond to find factories to team up with who are better for the environment–and just as importantly, are great places to work! Their Nanchong factory has a gourmet cafeteria and outdoor recreation equipment including everything from cardio machines to a basketball court!

Shop all silk camisole colors: 

The Bag:

This is my latest Everlane bag (my first was the Market Tote!)–but this one is what I’ve been reaching for most frequently! I love how the strap is widely adjustable–so it can be anything you want it to be–ranging from a shoulder bag to a cross-body. (It’s particularly great for moms who need easy access to what’s in their purse, enough room to fit lot’s of essentials, but a cross-body so they can have their hands free!) It fits a laptop and has a magnetic closure so you’re never fumbling around with the zipper!

Other Boots You Can Wear To The Office:

Now friends, of course there are other boots and booties you can wear to the office! Here are some other types of ankle boots in different colors and styles that will still get the job done. (Pun intended!)

  • Midi Boots
  • Knee-high Boots
  • Chelsea Boots
  • Oxford Boots
  • Flat Heel Boots

Everlane The Form Bag[one-half-first][/one-half-first][one-half]

Everlane The Form Bag

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How to wear ankle boots to work

Was this post helpful? I hope so! Would love to know what other Everlane items or business casual booties you love wearing for work! 

This post is sponsored by my favorite brand, Everlane! All opinions are 110% my own! Thank you for supporting the brands that allow me to keep creating the best possible content for YOU–my girls! ❤️