Work Attire Inspo for Winter

Hi, friends! Happy Monday and welcome to a new week of experiences and opportunities! In today’s post, I’m going to share some work attire inspo with you! Something about wintertime makes me feel uninspired with my wardrobe, and I’m sure some of you feel the same. I love looking to others for inspiration, so I figured this post would be helpful to anyone who’s in a winter funk with their wardrobe.

I don’t really take things out of my closet as the seasons change. I like to think that my wardrobe is pretty versatile. I try to buy things that layer well, but since jumping onto the conscious shopper bandwagon, I haven’t bought anything in a while. So, today’s post is all about digging into my closet and sharing some of my favorite things to wear to work in the winter.

I’ll preface this post by saying I’m extremely fortunate to work in an office with a dress code that pretty much aligns with my personal style. Although I probably couldn’t wear my Vans in the office, I can wear my Dr. Martens — and that’s all I need! Of course, there are some small restrictions when it comes to my dress code, but those restrictions don’t really apply to me because I never wear those types of things anyway.

When I left Anthropologie for my current office job, my work attire did change slightly, but not by much. I would say the thing I miss most about my work attire at Anthro was the ability to wear graphic tees. You all know I love my graphic tees! But, it’s okay, because my collection is still growing and I just wear them when I’m not at work!

Okay, I’m done rambling. Let’s get into some work attire inspo for winter!


I live for skirts. I never really used to like them, but I’ve learned to love them over the past couple years. As much as I enjoy wearing jeans, I’ve had some issues with sizing and fit — and honestly, I just feel more comfortable in skirts most of the time. My FAVE place to find midi skirts is Urban Outfitters. Once you weed out the body con and super-high slit skirts, they have a lot of great options. I always shop their sale rack for skirts, too, because it seems like no one else is buying them but me! This skirt is not the best example because I wouldn’t wear this high slit to work LOL, but I love the skirt anyway!

I like throwing on a cozy sweater with a more fitted midi skirt. Plus, I tend to get cold when sitting at my desk, so a chunkier sweater like this keeps me warm all day long.

Let’s talk shoes. I can’t leave the house in the winter without my Dr. Martens! I tend to alternate between my Leona pairs and my Rometty Chelsea pair. I know that Dr. Martens might not seem like “work-attire,” but ya know what, I have to be a little bit edgy, so I wear them whether I’m supposed to or not!


Work attire in the winter is difficult for me because I don’t want to worry about the temperature outside. I want to wear whatever I want! That’s definitely one of the biggest things I miss about living in South Carolina. The freedom of getting dressed in the morning!

Anyways, this outfit incorporates another skirt, of course, but I’ve layered it with a blouse and jacket. I love layering, and although I don’t really like Cleveland winters, I do like layering fun textures and patterns. When I’m choosing blouses to wear with a skirt, I look for ones that have less volume, or ones that I can easily tie. I’m all about the knot when it comes to blouses and skirts. I really hate tucking blouses into skirts because I feel like a corporate crony, so I try to avoid it as much as possible!

I finished off this look with my Everlane Day Heels. Holy moly guacamole — if you need a high-quality pair of short heels in your wardrobe, BUY THESE. Yes, they are expensive, but the quality is unmatched, in my opinion. I’ve never worn a pair of heels that were more comfortable than these ones. I’ve worn them for 8-hour shifts at Anthro and in the office.


Alright, this one’s for anyone out there who hates wearing skirts. I see you, and I hear you! My dress code at work allows jeans, but as I said before, I’m kind of struggling with jeans right now, so I really don’t find myself wearing them to work. I love a good colored or patterned pant, so that’s usually what I end up wearing.

I’ve had this pair of patterned pants for YEARS. The great thing about them is that the pattern is so crazy you don’t notice how worn they look. Maybe I should get rid of them, but will I? Not anytime soon!

If I’m wearing pants at the office, I like to pair them with a tunic or more elevated blouse. When I do that, I feel more like me — if that makes sense. But, you could tone it down if that aligns more with your personal style.

I chose to wear my Dr. Martens again because, well, most pants are too short on me. I actually think that every pair of pants I own are unintentionally cropped. So, I tend to wear boots with pants or jeans to deflect from the fact that they’re too short. I feel like when I wear these boots with pants, I have to keep my accessories more polished so the look doesn’t become too edgy for the workplace.

Well, that’s all I have for ya! A little inspo for work attire in the winter! I hope that your week is filled with good vibes and I’ll see you again on the blog this Friday!

Until next time!


Leave a Reply