Four Ways to Wear Boots to Work

Pumps and flats look great with all of your work outfits, but they do nothing for keeping you warm in the winter. Today I’m sharing four outfit ideas for work with boots that are both comfortable and professional.

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Four Ways to Wear Boots to Work

Sizing Reference: I’m 4’10” and my bust, waist, and hip measurements are 32″, 24″, and 36″. My typical inseam is 24-25″. All of the outfits are unaltered and I list my sizing beside each item to help you compare and shop online.

With Full-Length Trousers

In past seasons where skinny trousers dominated trends for workwear, wearing boots felt confusing. How do you strike the right balance? (With a slim-fitting boot that tucks under the pants) This season full-length trousers are becoming more and more popular (although they’ve always been classic). This style is easy to wear with boots and you can even hide warm socks underneath as well. When I’m picking a pair of boots to wear to work I choose a pair that is dressier.

This black pair of boots dominates most of the outfits in this post. It’s the most comfortable pair I own for wearing to work and one of the most versatile. I find them to be true to size.

Four ways to wear boots to work via pumps and push-ups blog | petite style blog | petite fashion | petite friendly outfits for work | winter outfits for work

Pants Petite 00 | Boots TTS | Cardigan Sweater Petite XXS | Sweater XS | Necklace | Earrings

The next pair of boots I wear often to work has quite the heel on them, (which I love for wearing with pants that are a touch on the long side). I can walk in and wear them comfortably all day, but I sit at a desk for the most part. I find them to be true to size. The pants I’m wearing in this outfit are a budget option from Old Navy. They work well with a high heel for me (3″+) but are a little bit long otherwise.

Petite friendly ways to wear boots to work | petite style blog | work outfits | business casual outfits | winter work outfits

Pants Petite 0 | Boots TTS | Sweater Petite XXS | Sweater Blazer XXS | Belt XXS | Similar Belt | Necklace | Earrings

More Examples

With Leggings

When I talk about wearing leggings to work it always upsets someone. (so sorry) I’m definitely not talking about your basic athletic or even simple cotton leggings. I talking about an elevated option like a ponte or suede pair. Depending on your work environment and dress code, they can definitely be an option (they’re something I personally wear often). I love to pair them with black booties for a seamless (and warm) look.

Petite friendly ways to wear boots to work | warm winter work outfits | petite style | business casual outfits | smart casual outfits

Boots TTS | Coatigan Petite XXS | Sweater Petite XXS | Leggings Petite XXS | Necklace | Earrings

With a Skirt

Similar to wearing leggings with your boots, they also look great with tights and a skirt. You can skip the tights if you don’t need them, but I most definitely need them where I live. You can also wear knee-high boots to work with dresses and skirts, but I love how the booties keep the leg line slim instead of adding the weight of a knee-high boot. Fit notes on the skirt, I sized up to a size 4 based on the reviews and I could have stuck with my true size 2 at Boden.

Winter work outfits with boots via pumps and push-ups blog | petite style blog | petite fashion | business casual outfits

Top Petite XXS | Skirt 2 | Boots TTS | Tights | Coatigan Petite XXS | Earrings

There are other ways to wear boots to work during the winter and I will continue to share more! I’m also on the lookout for a great waterproof pair for my friends that work in snowy/wet areas. If you have a pair you love feel free to send your recommendations my way!

-Brooke

Brooke of Pumps and Push-Ups - petite style blogger

Hello, I'm Brooke!

A petite (4'10") gal on the hunt for the best petite clothes. I show you where to shop for petite finds, and how to style them in my weekly style sessions. I don't alter or hem any of the clothing on my blog - what you see is exactly how the items fit me right from the store.

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Pumps and Push-Ups participates in affiliate programs, including Rewardstyle and the Amazon Associates Progam. Pumps and Push-Ups earns commissions from qualifying purchases made through links posted.