How To Style Business Casual Pants With Boots In the Winter to Cover Your Ankles

How to Style Business Casual Pants to Cover Your Ankles

Wondering how the heck to wear pants for work in the winter so that your ankles stay covered? This question comes up a LOT, so let’s talk! 

First, as I often say, we have to start with the right pieces. Style is extremely difficult when you have the WRONG pieces. If you caught my free style class, 6 Common Style Mistakes + 3 Keys to Fix Them, you’ll remember that I said that style is like a puzzle, and you need the right pieces to be able to do the puzzle easily. If you are working with the wrong pieces, that puzzle is going to be extremely difficult to complete. So, for business casual style in the winter, you’ve gotta start with the RIGHT pieces. In this case, you’re trying to fit the right pants with the right types of shoes.

A lot of women run into the problem of trying to wear skinny ankle work pants with ankle boots and find that it just doesn’t look right. Oftentimes, the boots that seem to work well with jeans just don’t work with skinny ankle work pants. And even if they did, your ankles still would be exposed. If that combo doesn’t work for you, then I recommend switching to different puzzle pieces in the winter. I know nobody wants to have to buy different pants and shoes for the winter. And you know me—I really like to maximize the heck out of pieces and want the same for you. But if your winter weather is more extreme, then unfortunately it just may require different puzzle pieces. (Of course, if you don’t wear skinny ankle pants to begin with and wear straight leg or bootcut jeans year round, then you probably don’t have this problem to begin with and don’t have to switch your puzzle pieces! 🎉)

Before we get to the puzzle pieces, I know a lot of women actually wear all-weather shoes for the commute or simply to get from the car to the building and then change footwear to better coordinate with their outfit once they’re inside. That’s an idea if you want to go that route, but if you want an alternative, then let’s keep going.

SIZING INFO: I’m 5’6″ and usually S/M or 6 in clothes and 8.5 to 9 in shoes.

What to Look for in Pants

We’ll start with what to look for in pants. As it relates to shoes, you’re looking for pants that work with shoes that cover your ankles. So, pay attention to the:

  • cut
  • length
  • width of the leg opening


I recommend going for straight leg or bootcuts so that the leg openings will be wide enough to fit over your ankle boots. You can TRY it with the ankle length skinny pants. However, like we talked about, I find it’s often hard to get skinny ankle pants to fit properly with booties and still cover your ankles. Either they’re not skinny enough at the bottom to work with booties or they’re not wide enough at the leg opening to go over booties. And that’s why straight leg or bootcut pants are important.


For lengths, you want bootcuts to hit around 1/4” to 1/2” off the ground.

For straight leg pants, you have a couple of options, which are the same ones I mentioned in How to Style Straight Leg Jeans. You want them to hit at either a) ankle length, which would be anywhere from just above your ankle bone to about 1” above it, as shown below:

Where Straight Leg Jeans Should Fall on Leg Casual Outfit: white puff shoulder short sleeve tee + light blue straight leg raw hem cropped jeans + suede tan flats + gold pendant necklace

Or you could go for option b) full length, which would hit at the top of your instep.

I personally prefer ankle lengths, particularly when it comes to jeans, for a more modern and fresher look. Plus, it’s really versatile as that length works really well with lots of shoes styles in warmer months, which I show in the How to Style Straight Leg Jeans post. However, for whatever reason, with work outfits and work pants, I feel okay about full length pants. Obviously it’s up to your personal style and what you’re going for, but just some food for thought!


Leg Opening

Work Pants with Boots Elevated Business Work Outfit: red long sleeve sweater + navy blue straight leg slacks + cognac heeled boots + gold pendant necklace

You just want to make sure the leg opening is wide enough to fall over an ankle boot without bunching up or getting caught too much, especially when you move around a little. I don’t have a specific measurement for how wide I want personally want leg openings to be, as a variety of widths would work. But I just wanted to name this as an element to keep an eye on since it does matter. If the pants aren’t wide enough at the bottom to fall over an ankle boot, then your puzzle pieces aren’t gonna work.

Okay, pretty simple, right? Go for straight leg or bootcut, get the right length, then just be mindful of the leg opening.

For what it’s worth, bootcut pants work easily with most booties because the leg opening is wider and intentionally made for boots. (Hence the name bootcut!) Straight leg pants take a bit more intentionality and searching to find the right pairing, but it’s not difficult to find.

BTW, the pair of straight leg pants I’m wearing above is LINED WITH FLEECE! The fleece isn’t super thick, but they are definitely cozier and warmer than typical pants! They are also VERY STRETCHY and very, very comfy. The waistband is incredibly stretchy as well! Find them in several colors and a variety of inseams from 28″-34″, HERE. I wear size M.

Let’s move onto shoes!

What to Look for in Shoes

Thinking in terms of puzzle pieces, if we’re starting with the right cuts and lengths of pants, then to find shoes that fit the puzzle, make sure you focus on these things:

  • the shaft is narrow enough to fit under the pant legs well
  • the shaft is high enough to fit under the pants by about 1-2” or more—at least enough so that the pants stay over the shoes with light movement

When it comes to ankle length pants, since we talked about having them hit roughly just above your ankle bone to about 1” above, look for booties that hit a little higher than that to ensure that your pants will fall over them and keep your ankles covered.

If you’re working with full length pants, your options open up a little more as you can wear booties with a higher shaft or go with ones that are a little shorter. Longer pants will cover booties that have a shorter shaft more easily and more often than ankle length pants.

How to Style Business Casual Pants with Boots to Cover Ankles: leopard print booties, cognac booties, taupe suede booties

Above is a picture of bootie with different shaft heights. The first is very low, the second is the highest, and the third is medium. I can wear the higher pair with BOTH ankle length and full length straight leg pants while the shorter pair only works with full length pants. The medium pair works with some pants and not with others, depending on the exact length of the pants.

Shop the Boots:
similar lower shaft (in “Leopard Suede”, not “V Leopard Suede”) | higher shaft | medium shaft

Also notice that the bootie with the higher shaft also has a fairly narrow and streamline shaft, which should help it fit under a lot of different straight leg pants. If the shaft were bulkier, like with thick laces, big buckles, or a slouchy fit, the shoe would need to be paired with pants that have a wider leg opening or are shorter, or else the pants would get caught on the bulky shaft.


Work Pants with Boots Elevated Business Work Outfit: black puff sleeve sweater + black straight leg slacks + cognac heeled boots + gold pendant necklace Work Pants with Boots Elevated Business Work Outfit: black puff sleeve sweater + black ankle length straight leg slacks + cognac heeled boots + gold pendant necklace side view

Above is a picture of the booties with the high shaft paired with ankle length pants. Even though I’m wearing ankle length pants, there are no gaps where my ankles are because the shaft of the boot is covering my ankles and compensating for the shorter length of the pants.

Work Pants with Boots Elevated Business Work Outfit: grey puff sleeve sweater + blue full length straight leg pants + leopard booties + gold pendant initial necklace

Above is a picture of the booties with the shorter shaft paired with full length pants. The full length pants fall easily over my shoes and keep my ankles covered whereas the ankle length pants were at an awkward height for these booties.

And, there you have it! It’s really a matter of making sure you’re choosing pieces intentionally to fit the right puzzle pieces together. Pretty simple once you know what to look for, right?

So, when you’re shopping, find straight leg (wide or narrow, doesn’t matter) or bootcut pants that you like. Then, look for shoes that work with those pants, keeping in mind the height and width of the shaft.

Options for Pants for Work

Here are some straight leg and bootcut pants options for work! I wrote notes under some of the items, and if I’ve tried any of them, I listed info on material and sizing.

Options for Booties for Work Pants

If you need a few suggestions for booties that might work with some of the pants above, I rounded up some options below. Some seem like they could be good for both full length and ankle length pants, while some might only work with full length pants. Just keep in mind what you’re looking for—ones that are tall enough and narrow enough to fit under whatever pairs of pants you’re working with!


GREAT NEWS, friends! We now have a WINTER Business Casual Starter Kit Wardrobe Guide available in the shop!

There is plenty of winter weather left, and this guide will help you feel warm AND stylish in a snap! Complete with a shopping list, outfits, style tips, and a bonus shopping guide with links to available clothes, you’ll have everything you need to look put together and professional.

Check out the Winter Business Casual Starter Kit Wardrobe Guide HERE!

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