Winter workwear can be a chore when you don’t know what you’re doing! You, like everyone else, want to achieve the perfect balance of sophisticated and stylish without sacrificing comfort, warmth, and health. You’re exhausted from wondering what shoes to wear with dress pants in winter without losing one of your toes.
And, you’re tired of freezing your feet off every single day because you think you have to wear stiletto pumps to work. Navy blue tailored trousers, crisp white button-downs, and clean-cut blazers don’t go with Moon Boots. Pleated skirts and structured coats don’t go with chunky combat boots. Or do they?
Why don’t we take a page out of Hailey Bieber’s book and combine a suit set with our favorite chunky sneakers for a cool girl moment? Why don’t we copy Meghan Markle and combine wide-legged trousers and a cashmere turtleneck with suede booties for a dash of elegance?
Nothing’s stopping you from creating the look you want to wear every single day for the rest of the winter. When you start wondering what shoes to wear with dress pants in winter, don’t forget you can look polished and put-together and be comfortable at the same time.
We’re bringing you a guide to winter workwear to make sure you have your options laid out for you. And, we’re bringing you fourteen styles of boots that can work for every event you might need to attend while working through the winter.
1. Classic ankle boots
You can’t go wrong with the classics, right? Whenever you’re wondering what shoes to wear with dress pants in winter, remember that ankle boots exist.
We’re quick to think we have nothing to wear during the colder months because we’re tired of the weather, of wearing chunky, heavy clothes, and pretty much everything else that comes with winter.
But, ankle boots are there to save the day! When you don’t have a clue what to wear to a meeting, combine your dress pants with a cashmere sweater, leather booties, and a leather handbag for everything you might need, and you’re done.
Whether you go for the high-heeled ones or you stick with something more comfortable, you’re guaranteed to look put-together. Bells & Becks The Livia in Deep Red are great for a pop of (festive) color, but we would go with Khaite Admiral ankle boots for everyday wear.
2. Chelsea boots
We could go on and on about Chelsea boots, but we won’t. We’re only going to emphasize the fact that Chelsea boots have been around for decades and decades and they haven’t gone out of style once.
We’re pretty sure that attests to the fact that Chelsea boots are a great way to elevate your office attire and complement your dress pants.
Stop wondering about what shoes to wear with dress pants in winter, and start scouring the world wide web for high-quality, durable Chelsea boots.
Our favorite picks at the moment are Crockett and Jones Bonnie Chestnut Burnished Calf, Celine Cruiser Boots Chelsea Boot with Metal Toe in Calfskin Black, and slightly more affordable Asgard Short Rain Boots.
Wear them with cigarette trousers, cropped dress pants, and wide-legged trousers because they work wonderfully with everything. Combine them with soft, cashmere sweaters, structured button-downs, and chunky cardigans.
Leather accessories (handbags, gloves…) add a whole new vibe to the entire ensemble.
3. Knee-high boots
Depending on how forgiving your office can be, you can always channel your inner Kendal Jenner or Emily Rajkowski and wear a statement blazer, sheer, black pants, and knee-high boots – with no dress pants whatsoever.
But, when you are wondering how to style your dress pants for the winter, you might want to go with knee-high boots. Now, wide-legged or flared trousers would beat the purpose of knee-high boots because you wouldn’t be able to see them.
Knee-high boots as a way to make a fashion statement while you’re wearing layers and layers of knitwear on the upper part of your body. Tuck your cigarette trousers or tighter dress pants, combine them with a turtleneck and a blazer, and you have a similar style without angering your HR department.
What are our favorite styles for the season? Schutz Maryana Pointed Toe Boot and Staud
Women’s Wally Boots, of course. But, don’t exclude the possibility of finding really great deals at Zara, Mango, and Asos.
4. Platform boots
Maybe you’re addicted to sporting espadrille wedges during the summer. Perhaps you can’t fathom wearing anything other than platform pumps or chunky loafers during the colder months.
Whatever the case, you’re probably looking for something that’s going to add a little bit of height to your workwear looks.
Platform booties might be just the thing for you! With the trendy silhouette inspired by the 80s and 90s, you shouldn’t face trouble trying to find a style that works for you. From super high-heeled platforms to platform soles, there’s something for everyone who’s looking to appear a little taller during the winter.
Steve Madden Cobra Boots are the tallest you can go, but Vagabond Shoemakers Brooke Platform Boot and might be more comfortable and safe for a job interview. Doesn’t that make you want to go shopping ASAP?!
5. Chunky combat boots
Chunky combat boots are for those of you who love adding a little drama to your workwear. More often than not, you’re not allowed to experiment too much because you’re supposed to wear something appropriate, sophisticated, and polished.
Most offices are strict about what you can and can’t wear, but chunky combat boots almost always make the cut as appropriate footwear. Chunky combat boots are really great at adding an edge to your office attire. Maybe you have a completely different style from what you typically wear to the office.
Perhaps you’re bored of tailored trousers, structured button-downs, and stilettos. Whatever your reasons might be, chunky combat boots can make your winter workwear much more bearable.
ASOS DESIGN Wide Fit Anastasia Chunky Hiker Lace Up Boots and Charles & Keith Lace-Up Platform Calf Boots work great, but you can’t go wrong with the always stylish and current Dr. Martens.
6. Waterproof boots
Never again do you have to come to work with your feet soaking wet because the winter weather doesn’t respect your office wardrobe guidelines.
Oh and, never again do you have to wonder what shoes to wear with dress pants in winter without breaking the same guideless. Opt for waterproof boots, Wellies, Hunters, or whatever rubbery botties speak to your style.
We know what you’re thinking. “Are waterproof boots appropriate for work?!” Why wouldn’t they be, though?
They’re trendy, they’re easy to wear, and they’re guaranteed to keep you warm, dry, and comfortable throughout the day (even when you have to spend most of your day running errands for your boss).
Waterproof boots can be the fashion statement you’ve been waiting for. Combine them with tucked dress pants and chunky cardigans or with wide-legged trousers and structured button-downs. Hunter Original Refined Matte Rain Boots and Everlane Rain Boots are celebrity-approved favorites.
7. UGGs
Who doesn’t appreciate UGGs for the warmth, comfort, and snugness they provide?! We could argue that UGGs get a bad reputation for being “the ugly boots” or the boots associated with girls who love sipping on Starbucks Pumpkin Spice Lattes and taking selfies.
Sure, UGGs aren’t everyone’s favorite workwear wardrobe staple, but they should get at least some recognition. And, they might even be this year’s comeback shoe because they’ve been seen on pretty much every fashionable celebrity ever.
Dua Lipa, for example, wore an anything-but-simple pair of UGGs lined with shearling and decorated with grommets. Kendall Jenner, on the other hand, hasn’t stopped worshipping her mini UGGs and wearing them everywhere.
Since we love copying celebs, we suggest you combine your dress pants with an odd pair of UGGs (rather than the classic ones) and see what happens.
8. Stiletto boots
Stiletto boots might not be the first thing you think of when you’re wondering what shoes to wear with dress pants in winter, but…
We would argue that stiletto boots should be a winter workwear must-have because you never know when you’re going to have to attend a meeting or an event where you would want to look your best. And, stiletto boots make sure that you do.
Sure, stilettos aren’t meant to be worn when you’re running late to work, the streets haven’t been cleaned from the snow that was pouring all night long, and you haven’t had the chance to learn how to walk on them.
But, there’s a time and place for everything, and stiletto boots deserve a spot on our list because they’re the ones that work best with dress pants. Whichever style of tailored trousers you go for, stilettos have your back.
Larroude Kate Boots and Amina Muaddi Jahleel Suede Over-The-Knee Boots have a hold over us, but you don’t have to choose them. There are plenty of other styles to choose from, too.
9. Sock boots
Sock boots are another style of shoe that’s got a bad reputation.
They were popular for quite some time, and celebrities such as the Kardashians couldn’t get enough of them. They were flattering because they were tight and figure-hugging. And, they were simple to style because they were made with different fabrics, patterns, and heel heights.
So, we think as though we need to have them on the list because they’re bound to work with dress pants. Whether you go for tailored shorts, cropped, ankle-length dress pants, or wide-legged trousers, you’re probably going to find a pair of sock boots that work with every style.
And, sock boots tend to give off that elegant, effortless energy which means you can wear them to meetings and events, as well as your everyday work activities. Stuart Weitzman Stuart 75 Sock Booties, Chloé Nellie Western Sock Booties, and Rag & Bone Brea Corded Sock Bootie happen to be our favorites.
10. Cowboy boots
Time to giddy up for work, apparently! While we would never think of cowboy boots as work-appropriate attire, we’re happy to announce that they’re as stylish, sophisticated, and on-trend as you might think.
So, when your boss asks you why you’re wearing cowboy boots at the office, don’t shy away from saying something along the lines of “because Anna Wintour says these are the season’s best boots!“
Western styles seem to be making a comeback (not that they ever left), and they’re pretty easy to style when you know what to look for.
Combine your tailored trousers with a structured button-down, a statement leather belt matched with leather cowboy boots, and a chunky cardigan with embellishments and embroideries.
Boho style doesn’t have to be reserved for Coachella when you can have just as much fun styling such summer pieces for winter, too.
We’re rooting for Ganni embroidered leather knee boots and Isabel Marant Duerto leather boots, but you can go for whatever cowboy boots you prefer.
11. Shearling boots
Now we’re getting somewhere slippery! When you’re trying to rack your brain around what shoes to wear with dress pants in winter, you’re probably tormented by the idea of what you need to look like at work. Maybe you have office rules that state you need to wear stilettos.
Perhaps your boss argued how you and your colleagues need to look alike without wearing uniforms. But, there are times when you’re the only one that thinks you need to look like you work at a law firm.
And, when that’s the case, nothing is stopping you from broadening your horizons. Shearling boots happen to be the trend of 2022 and they’re probably going to be just as popular later on.
Winter weather can’t harm you when you’re wearing shearling boots, and you can easily combine them with other shearling accessories to create a cohesive look.
Max Mara Shearling Midi Boots would look lovely under wide-legged trousers, and La Canadienne Victor Waterproof Suede & Shearling Combat Booties would work with the cigarette and cropped trousers.
12. Quilted boots
Quilted boots are a novelty, but they’re pretty much the only winter boots you need! Sure, stiletto boots and sock booties make you look more polished and presentable, but quilted boots are guaranteed to give you that cool girl vibe and keep you warm.
What shoes to wear with dress pants in winter, you wonder? Quilted boots, of course! Combine your quilted boots of choice with a quilted coat and you’re going to turn some heads at the office.
Dress pants and quilted boots work together because the boots are supposed to be the statement piece of the outfit. Wear your dress pants with something as simple as a cashmere sweater or a chunky cardigan to make sure you draw attention to your quilted boots.
Monochromatic moments would work great, but you can always keep things simple without sacrificing the rest of the color palette.
And, before we forget, some of the celebrity-approved quilted boots are Mango Platform Quilted Ankle Boots, Prada Triangle-Print Weather Booties, and Christian Louboutin Oriona 100 Rubber-Trimmed Quilted Padded Shell Ankle Boots.