How to Wear Ankle Boots With Pants for Work – Straight Leg and Skinny Pants

2 Ways to Wear Ankle Boots for Work

Huge thanks to Macy’s and ShopStyle for sponsoring this post

Hello, friends!  Today we’re hitting a question that’s asked often as cooler weather kicks in: how to wear ankle boots with pants for work.  Ankle boots are necessary when temps dip and you want to keep your feet warm, but many of you have said they’re tricky to style for work, especially with pants.  I’ve got a few tips and fail-proof combos to make it easy to style ankle boots with pants, and today I’m partnering with Macy’s and ShopStyle to share them!

A ton of Macy’s items are currently on sale, and more are an EXTRA 25% off for their Customer Appreciation Event with code THANKS from October 16th-20th.  There’s such good stuff at very affordable prices, so I’ll be sure to highlight them below!


What I Look For in Ankle Boots for Work

First, I’ll start by saying that what I look for in ankle boots for work is different than what I look for in ankle boots with casual outfits.  For casual outfits, I prefer suede booties with a rounder, almond toe, usually a lower shaft, and a thicker block heel.  To me, the almond toe and thicker block heel keep casual outfits relaxed.  However, I like workwear style to be a little sharper and more tailored.  To achieve this, I recommend starting with booties that have:

1. A pointy toe.  Nothing extreme, but enough of a point to add crispness.  A pointy toe also helps extend the leg line, which is especially helpful with straight leg or bootcut pants.

2. A skinny kitten heel.  While most of us would rather wear flats everyday, sometimes you need a tiny lift for ankle boots to work well with pants.  A kitten heel is very short and easy to walk in, and the skinnier heel provides a sharper, more polished look.

You can absolutely deviate from booties like these and still create polished work outfits.  But, if you’re looking for a starting place and want a style that’s classic, versatile, and works almost every time, this is a style I’d recommend.   Booties like these can be worn for casual outfits too, depending on your style.  They are also great for dressy casual looks!

At the bottom of this post, I’ll round up more ankle boots like these.  Right now, let’s get to the tips for styling them!


business casual + maroon polka dot top + maroon moto jacket + black straight pants + black booties + grey pursebusiness casual + maroon moto jacket + maroon polka dot top + black straight pants + black booties + grey purse business casual outfit + maroon polka dot top + black straight pants + maroon moto jacket + black booties + grey purse maroon polka dot top + maroon moto jacket + black straight pants + black booties + grey purse + business casual outfit

Wearing Ankle Boots for Work – Straight Leg Pants

Straight leg pants work great with ankle boots!  But, there are a few key things to make it work:

  • Aim for a shorter hem so that the pants extend over the shaft of the boot just a little instead of covering the boot completely.  Straight leg pants, unlike bootcut pants, often don’t have a wide enough leg opening to fall cleanly over the entire boot and may result in the material bunching around your shoes.  A shorter hem works better with straight leg pants, hitting around your ankles.  And, great news–this style is trending right now!
  • Use a bootie with a higher shaft.  This is very helpful for getting this look right, so that the pants and boots more or less look like one continuous line.
  • Choose booties with a pointy toe.  Your ankle boots can have other toe shapes, but I find a pointy toe is the easiest to start with.  It elongates your leg line, and it adds a crisp and polished factor to outfits.

These booties have a shaft that hits about 1 to 1.5 inches above my ankle bone.  The upper is flexible, and while it feels decently comfortable overall, I would add a shoe insert to have more cushion in the footbed.  One note is that they do show a bit of creasing around the ankles.  Otherwise, the silhouette is great, and they come in black suede, a beautiful tan suede, olive suede, leopard print suede, and snakeskin.  See them HERE!

I tried to do this look with ankle length slim cut pants, not true straight leg pants, and it did not work.  True straight leg pants are a must.  The straight leg pants I’m wearing above are by JM Collection, and they’re awesome!  They are fairly thick, VERY stretchy and comfortable, super affordable, and only available at Macy’s!  They have a wide elastic waistband throughout, though no pockets or zippers.  They feel like thick yoga pants!  And they’re under $24!  Check them out HERE.  I wear size S.

Lastly, I want to mention this faux suede moto jacket by Style & Co, which is another item only available at Macy’s.  It’s SO STRETCHY and comfy!  If you like the look of moto jackets but have always worried they’d feel too stiff, hard to move around in, and impossible to keep on most of the day, you should try this one!  You get the structure that moto jackets provide, with ultimate comfort.  It comes in 4 colors, which you can see HERE.  It runs pretty large, so I’m wearing XS, but if I wanted a little more room in the arms I’d go for S.

Shop the Outfit
Top: c/o Macy’s (exact–wearing size S)
Jacket: c/o Macy’s (exact–wearing size XS)
Pants: c/o Macy’s (exact–wearing size S)
Booties: c/o Macy’s (exact–wearing size 8.5)
Bag: (exact)


business casual outfit + burnt orange blouse + black skinny pants + leopard print booties + grey purse business casual outfit + black skinny pants + burnt orange blouse + leopard print booties + grey purse burnt orange blouse + black skinny pants + leopard print booties + grey purse + business casual outfit leopard print booties + burnt orange blouse + black skinny pants + grey purse + business casual outfit

Wearing Ankle Boots for Work – Skinny Pants

For pairing ankle boots with skinny pants, any of these options work:

a) Leave a small space between your boots and pants, showing a peep of your ankles.  You can cuff your pants outward to achieve this, or cuff them inward for a cleaner hem.  I did the latter above.

b) Leave no space and instead let the pants graze the top of the shaft.

c) For booties with a higher shaft, try A or B, or tuck the pants into the top of the boots a bit.  You’ll have to play with this one based on the specific pants and booties you try to pair.  A little bunching is okay, but you don’t want so much that it starts to look messy, especially for work.

Many people have asked how to wear ankle boots with skinny ankle pants, which often flare out a little at the ankles.  I haven’t quite mastered that yet and always find it looks funny.  Instead, if I want to do ankle boots with skinny pants for work, I go for pants that are really fitted at the ankles, like the ones above.

The skinny pants above are another pair exclusively at Macy’s, and they are extremely stretchy, fairly thick, and a pull-on style with a wide, elastic waistband.  They basically feel like really, really thick leggings!  They retained shape after several hours of wear.  One note is that there are seams down the legs that you can feel on the inside.  I got used to them after wearing them for a while, but just wanted to give you a heads up in case that might bother you.  These are too long for me at 30″, so I cuffed them inward to bring up the hem without having to go to a tailor.  The ankles are very fitted, which helps create a continuous, clean line with booties.  If you want a comfy pair of skinny pants for work, check these out!  They are currently $37.  See them HERE.  I’m wearing size 4.

For this outfit, you could keep it streamline with black booties, but I wanted to make it pop with leopard print booties!  Because, hello 😍! These things are 🔥!!!  And, they’re COMFY!  They have a bit of padding in the footbed for comfy wear.  The upper is flexible and has subtle, soft lining that feels good against your skin.  They are on the pricier side, but the quality and comfort shows for it.  They come in leopard print, black suede, black leather, and grey suede.  See them HERE!

Lastly, I LOVE this top!  It’s simple but stylish and very easy to wear–right up my alley!  It looks nice without looking like you’re trying too hard, can be worn to work, and can be worn in a polished, casual outfit.  It’s created just for Macy’s and comes in a whopping 16 colors!  I’m wearing Rusty Red which looks more like a gorgeous muted burnt orange in person.  The color doesn’t look quite right on Macy’s website.  It’s closer to my pics above, but slightly more muted.  It’s even more beautiful in person!  It’s got 200+ reviews and 4.5 stars!  Currently under $28!  See all 16 colors HERE.  I wear size S.

Shop the Outfit
Top: c/o Macy’s (exact–wearing size S)
Pants: c/o Macy’s (exact–wearing size 4)
Shoes: c/o Macy’s (exact–wearing size 8.5)
Bag: (exact)

If you need help getting ankle boots to look right with work pants, start with finding ankle boots with a timeless silhouette, pointy toe, and small heel.  Then, pay attention to how the hem of different pant cuts hit the shafts of your different ankle boots.

Below I’ve rounded up more similar ankle boots.  I’ve tried many of them, so look underneath each item for my comments on comfort and sizing.  Swipe through to see them all, and click to shop!

Do you have any more tips for pairing ankle boots with pants for work?




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