Stylist’s Guide to Women’s Workwear in Winter (and All Year)

September 13, 2024

As a professional stylist–and as a woman who’s been there–I know firsthand the challenges of figuring out women’s workwear. Decoding office dress codes can be a pain, especially when you want to look polished and still feel like yourself.

That’s why I’ve created this one-stop guide to simplify things. I’ll break down every dress code from business formal to casual Fridays. Plus, with winter on its way, I’ve got specific style tips to help you dress sharp in cold weather. (After all, you deserve to look great, stay warm, and feel confident, regardless of the season or office.)

But before we get into the nitty gritty of dress codes, let’s take a step back. Why have dress codes become so confusing anyway?

How Workwear Dress Codes Have Changed Over Time

Dress codes have always been a part of fashion history. But the path hasn’t been as clear-cut for women as it has been for men. While men and women throughout the 1900s were expected to dress well, the implications and pressure were harsher for women.

I’ve felt firsthand that pressure to look perfect just to be taken seriously. It’s not just about clothes. It’s makeup, hair, and balancing “professional” with “feminine”. 

Not to mention the fact that, generally speaking, women didn’t have office jobs until the 1920s and 1930s, it wasn’t until then that women held positions as clerks, stenographers, and bookkeepers. 

Fast forward a bit to the 1950s-1970s and you arrive at the Mad Men style dresses and skirt suits. Hemlines got shorter (Knee length might not seem that wild to you and me but it was at the time. And don’t get me started on women actually wearing pants to work!)

That said, from the 1980s onward, the expectations of what women’s workwear clothing looked like held firm. Office culture is defined as more formal, structured pieces. Suits, heels, and pressed blouses were the go-to for many women, not just in corporate or legal fields. 

Then COVID-19 changed everything. Fashion took a sharp turn towards casual in every department. Remote work became common and suddenly, comfort was the name of the game. Many of us traded our tailored pants for leggings and sweats. (Yep, even yours truly found herself in workout pants in a couple of Zoom calls.)

So where are we now?

While the pandemic didn’t magically take away the societal expectations we experience as women, things have shifted. You no longer have to choose between looking professional and being comfortable.

Why Does It Matter What I Wear To Work?

What you wear to work matters because first impressions are everything. Studies show people form lasting opinions about you in just seconds. As a woman in the workplace, those opinions often go beyond your achievements. People–whether clients, colleagues, or leaders–are paying close attention to how you present yourself. And let’s be real, people judge women differently than men.

It’s not just about clothes. It’s about how you speak, body language, interests, and interact with others. Society often expects women to look polished and put-together at all times, with little guidance on what that means. 

For example, have you ever gotten the “you look tired today” comments on a day when you didn’t wear makeup? But on the other hand, have you gotten comments about “doing too much” when you wear a bright red lip?

I know it’s overwhelming to think that so much of how you’re perceived at work comes from your appearance.

But you have a choice: let those expectations get to you or recognize them and use them to your advantage. Workwear for females may not be an easy topic, but it’s a necessary one.

This is where having a system and a knowledgeable stylist comes in. I’ve styled hundreds of women with my company, Next Level Wardrobe. I’ve heard their concerns, from how to dress their mid-size body to how to put an outfit together. I’ve heard their goals of getting that promotion or starting a new company. 

I’ve developed a simple style system that works with you, not against you. It takes the guesswork out of what to wear and helps you feel confident. You’re an expert in your field, and I’m an expert in mine. I know how much easier life gets when you take the stress out of getting dressed. So why not make your workwear effortless?

What Colors Should I Choose for Stylish Women’s Workwear?

There are no strict rules when it comes to choosing the colors of women’s workwear clothes. The most professional and versatile colors include black, grey, navy blue, and white.

Anyone can wear any color. The real thing to focus on, instead of “right” or “wrong” colors, is intentionality. So how do you go about that?

Cue the Next Level Wardrobe Style System. My system has worked with over 250+ clients, helping them build stylish, functional wardrobes. Here’s the gist of it:

  1. Focus on core colors
  2. Prioritize fit
  3. Quality over quantity

1. Core Colors

These core colors form the foundation of any stylish wardrobe. Why? Because they’re easy to mix and match, look polished, and can work in an office setting. Because of that, they should form the largest part of your closet.

2. Tonal Colors

The second-largest section of your wardrobe should be “tonal colors.” These are tints, textures, and shades of the original neutral colors. They add depth and interest to your outfits without being overbearing.

3. Accent Colors and Patterns

Lastly, the smallest percentage of your closet goes to seasonal colors and patterns. This is where you can show off your personality or tap into seasonality. For example, with winter around the corner, this is the place to add a holly red or an evergreen emerald. Just remember, these are accents. Use them sparingly and intentionally.

Pro tip: Bookmark this page and save our graphic above to use as a template for your closet. You may need to adjust the ratio to find what works best for your lifestyle.

Women’s Workwear Dress Code: Casual

If you work in a creative industry or are part of a casual, “no dress code” environment, you can still dress well. You don’t have to look sloppy just because you don’t have traditional business attire.

Focus on high-quality, well-fitting pieces in more casual fabrics for a more relaxed yet still professional women’s workwear look. Instead of slacks, choose jeans. BUT make sure they’re in tip-top shape—no rips or distressing. 

Stick to dark, solid washes and prioritize fit. Watch out for jeans that whisker excessively at the front or sag in the back. In terms of hem, go for nothing shorter than ankle length but nothing that’s dragging on the ground.
Instead of a traditional blazer, try layering a shacket. Need something for winter office workwear for women? Pop on an overcoat. These subtle adjustments let you stay comfortable while looking effortlessly put together.

Our Top 3 Casual Essentials

1. A High-Quality Tee

NLW founder Cassandra is wearing her essential t-shirt from Italy.

Let’s get one thing straight: I don’t mean any old Tee when I say you need a T-shirt for work. This is not the time to pull out that old college logo shirt, and don’t even think about reaching for that worn gym shirt you throw on over your workout set!

These are shirts that look nice enough to wear to the office. They’re clean, simple, basic, but high quality. They should feel soft but not look worn after only a couple of washes. 

We recommend looking for something like this crew neck from ATM. 

The fit is key for this style to look more elevated. It flatters and skims your shape without clinging to your body.

Product by ATM, shop here.

Pro tip: Want to winterize this piece? Trade it in for a long-sleeved version when the temperature starts to drop.

2. Denim

NLW Client, Sue wearing a casual denim look (far left)

What better to pair with your elevated Tee than a pair of jeans? Denim has come a long way from the rigid options of years past. Now, you have countless styles, fabrications, and rises to choose from. There’s something for everyone, and as someone who values variety, this makes jeans a must.

With versatility being the goal of your new capsule wardrobe, I suggest having a few different silhouettes. That way you don’t end up with a style boredom.

And remember how we mentioned color being your opportunity to engage in seasonality? That’s the idea with these black high rises from Paige. The wide-leg cut is right on trend without being “too trendy.” It’s also a more comfortable fit than skinny jeans.

Product by Paige, shop here.

3. Sneakers

Yep, you read that right. Sneakers at work aren’t just for Tech CEOs anymore. We’re calling sneakers a must-have for a modern woman’s casual workwear. But just like we’re not telling you to wear a crop top to the office, we’re also not telling you to wear Hokas or hiking shoes to your next meeting.

What you need are true daytime sneakers. These shoes should be something you wear only to work, never to work out. We recommend going for the classics. Start with a low-profile white trainer and build out from there. Like these low-tops from Veja pictured below.

Product by Veja, shop here.

Slip-on styles are also great for busy mornings. While these work great for most climates, they may not work for winter. 

In that case, we suggest going with a pair of flat or low-heeled black or brown booties. A Chelsea boot, for example, will never go out of style.

Women’s Workwear Dress Code: Business Casual or Power Casual

Women’s business casual is hands-down the most popular dress code we all encounter. Why? Well, it’s ideally the perfect balance. It should be where old school meets new and where relaxed meets structured.

But that also means it can be the most confusing to navigate.

What’s too casual? What’s too dressed up?

Here’s what I recommend: think of business casual as power casual. In other words, casual plus. Instead of drawstring joggers, go for a pair of dressy joggers with a zipper. Or sub out your jeans for a pair of trousers, but then bring it back down to earth with an easy-going sweater. You can incorporate sweaters, corduroys, or even a pair of linen pants for a business casual dress code.

You can also upgrade your shoe choice here. Again, boots reign supreme for winter. But a sensible heel or flat gets an A grade in my book for other seasons or warmer weather. 
So what are we recommending for women’s office workwear: women’s edition? Scroll on to find out.

Our Top 3 Business Casual Essentials

1. Blouse

NLW Founder, Cassandra wearing her work blouses.

Not exactly revolutionary, but blouses remain an essential part of any power casual or business casual women’s look. These pieces upgrade you in a snap. 

Think of ranking tops like this:

A T-shirt is the “little sister.” It reads as more casual. But a blouse is the “Big sister”; it reads as more formal. 

Adding a blouse to your style rotation helps with that versatility component. It’s a must for more formal events and environments, yet I see it missing from so many closets I review.

Product by Lafayette 148 New York, shop here.

Try something unique yet professional like this tie-collar blouse. The neck detail will help you stand out and show off your sense of style without seeming gaudy or “extra.”

(Oh yeah, and we’re not believers in the old white after Labor Day rule. You do you!)

2. Trousers

Trousers are a key part of any business casual wardrobe. They offer style, versatility, and comfort year-round, especially in winter when they can provide both warmth and polish. 

However, I know that trousers are also very difficult to shop for. I often hear from clients that they struggle to find trousers that fit, especially when they’re going through body changes. Learning how to dress your new body can be a huge hurdle.

Plus, how do any of us know how pants are supposed to fit when there are so many styles? 

This is where I recommend working with a stylist. I can point my clients to different brands, cuts, and styles that work best for their body and lifestyle.
So what style would I recommend to everyone? Wide-leg pants. They’ve been trending lately along with straight legs, and that trend isn’t going anywhere. Why? Because this cut looks good on everyone. You’re set as long as you find a pair that fits your body (this is where alterations come in the clutch).

Product by Altuzarra, shop here.

A pair of trousers I’ve been loving lately are these wool pants from Altuzarra. High-rise is great for lengthening your silhouette and the pleat detail is a subtly stylish touch.

The wool fabric also makes them a dream for wintertime. They’ll keep you warm without being too thick or bulky.

3. Comfortable Flat Shoes

Hardly any clients that I work with ask for 5-inch stilettos, and we understand why! It’s not exactly practical when thinking about workwear for women. If you are a busy professional, you’re always on the go, sometimes walking thousands of steps a day. You need your footwear to keep up with you. 

There are plenty of flat footwear options out there. But for the colder seasons, a loafer is an easy choice. You still get that touch of professionalism while keeping your feet safe and warm from the cold.

Product by Aeyde, shop here.

A pair like these from Aeyde in a cozy Mocha color will go well with your trousers and blouse. Add a coat, and you’re ready for the season.

Women’s Workwear Dress Code: Formal

Female workwear may have slackened, but not every office has casual Fridays and lets you wear sneakers. I get that. I’ve worked in industries where I had to stick to a formal dress code as well.

Unless your HR department says otherwise, it’s best to play it safe. Stick to blazers and suits or dresses. You can always switch up what color of suit or dress you wear to fit the occasion—for example, meeting with investors. A black blazer and trousers with sensible heels is the way to go. But if you’re speaking at a summit, you might want to stand out a bit. This might be the time to wear a dress in a bold color or a patterned suit.

There are always ways to look sleek without seeming uptight.

Our Top 3 Formal Essentials

1. Blazer

NLW Client, Susan showing off her new, modern pantsuit.

It should go without saying but a power blazer is a staple for every working woman’s closet. This is especially true if you work in a formal environment. But that doesn’t mean you have to wear some boring, over-starched thing from the 90s.

Say goodbye to the Ann Taylor blazer you bought when you first entered the workforce. This is the time to incorporate textures and different silhouettes. Much like with jeans, there’s something for everyone. You can go as fashion-forward as you like or keep it more traditional.

Product by Reiss, shop here.

This single-breasted blazer by Reiss is a perfect example. The long-line look feels contemporary and cool, and the rich plum purple adds a dash of personality without going overboard. 

On top of that, this fits with perfectly with a winter color palette. This is your moment to pull out rich, deep hues just like this.

2. Dress

NLW Founder, Cassandra, wearing her a-line dress in NYC.

It may surprise you, but clients often tell me that they love dresses. They take out the guesswork because there’s no outfit coordination involved. It’s a one-and-done, throw it on, and you’re good to go!

(This also makes them an MVP for frequent travelers. If you’re dressing for a work trip, cut down on your baggage by packing a dress. Fewer pieces taking up space in your luggage.)

I totally agree. They’re appropriate for many dress codes as long as you’re mindful about your hem length and neckline. I recommend (especially in a formal office) that you stick with at-the-knee or longer styles. I would also clarify with your HR department if you can wear sleeveless styles or if you need to cover your shoulders.

Product by Ralph Lauren, shop here.

For chilly days, something like this tie-front long-sleeve frock from Ralph Lauren is ideal. You’re staying dress code-friendly without looking frumpy. It’s fitted enough to show off your shape, and the tie-front waist defines your figure.

3. Skirts

NLW Client, Sarah showing off skirts she kept in her closet edited in some new looks.

As a stylist, I’ve seen so many workwear women’s clothing of all professional levels. You know what’s the one thing I wish I saw more? Skirts! 

In 2023 I visited Tokyo and felt inspired by the amount of skirts I saw women wearing. Skirts are unexpected, playful and–if outfitted correctly– look just as formal as pants.

Bonus: you can usually dress them down for the weekend! Swap out your blouse for a Tee or add on sneakers instead of ballet flats.

Product by ba&ash, shop here.

Something like this pleated midi skirt is perfect for every season. Pair it with knee-high boots for a cozy fall or winter outfit, or transition it into warm weather with white sneakers and a tee.

Transform your Winter Workwear Style

The change in seasons is the perfect time to rehaul your women’s workwear. But it can be overwhelming to do this on your own. For professional help editing your closet, finding your style, and taking the stress out of shopping, try Next Level Wardrobe. Apply for our Women’s styling services to work with our concierge styling team. We’ll listen to your goals and challenges and curate a wardrobe for your personal brand.

About the Author - Cassandra Sethi
About the Author - Cassandra Sethi

Personal Stylist & Image Consultant

Cassandra Sethi is a Personal Stylist and Founder of Next Level Wardrobe, a luxury Personal Styling and Shopping Service that helps successful professionals of all ages and sizes. After working in the fashion industry for over 25 years, she used her expert knowledge to create a proprietary styling system called ‘The Next Level Wardrobe Style System' which guarantees clients more outfits with less items in their closet. NLW has been featured in The Wall Street Journal, The Tamron Hall Show, NY Mag, Huffington Post and more.

*Disclosure: Next Level Wardrobe only recommends products that we’d suggest to our clients or personally wear ourselves. All opinions expressed here are our own. This post may contain affiliate links that at no additional cost to you, Next Level Wardrobe may earn a small commission. Read the full privacy policy here.

How to find your style quiz thumbnail

Take the Find Your Style Quiz

Uncover Your Unique Style in 5 Minutes

Cassandra Next Level Wardrobe Bio Picture

Cassandra Sethi

is a NYC Personal Stylist and Image Consultant. She is the Founder of Next Level Wardrobe and 'The NLW Style System' that guarantees clients more outfits with less items.

Related posts

Ready for a shortcut to great style?