3 Winter Must-Haves in Your Closet For Female CEOS

December 8, 2023

Every season, we’re all bombarded with endless ads and advice on what to wear. It seems like no matter where you turn, someone’s trying to sell you a whole new wardrobe. 

But if you’re a female CEO, you don’t have the time to switch up your closet every season. 

That’s why it’s more important to focus on quality over quantity. You’ll get more use out of 3 high-quality pieces that fit your lifestyle and body over 30 mismatched items that don’t. 

(Not to mention all the time and money you’ll save by investing in long-lasting pieces!)

Instead of telling you to spend hours online shopping, we’re here to take the fuss out of shopping. Using our NLW Style System, we’ve identified the three winter wardrobe must-haves for every female CEO. No matter your size or age, you should have:

  1. A Wool Coat
  2. A Cashmere Turtleneck
  3. A Midi Skirt

Keep reading to learn why these pieces are so powerful, how you can style them, and our specific product recommendations. 

Wool Coat

Mackiage wool coat for female CEO winter wardrobe

Product by Mackiage, shop here.

A wool coat is a chilly-weather staple. They have a classic look that you can wear to any office or occasion. Plus, wool is expert at keeping out the cold. 

We recommend wool because it’s a natural, cozy material that looks better and lasts longer than synthetic alternatives. 

If you’re looking to add one to your closet, consider this chic option from Mackiage. We love it because it’s simple yet modern. The coat features clean lines and a no-nonsense design that won’t distract from you or the rest of your outfit. It complements and completes instead of overpowering.

The belted silhouette is also a favorite because it defines your waist and looks good on all body types

How to wear: 

Need inspiration on how to wear a wool coat? Take a look at this before and after image from one of our very own NLW clients. On the right, you’ll see a wool coat in a pop of fuschia.

While we love neutrals, adding a splash of color via a layering piece is fantastic for freshening up your look. 

Compared to the “before” photo on the left, this outfit feels much more energetic and updated. 

But, it doesn’t feel busy. Why? Because we kept the rest of the outfit paired down with cohesive neutrals.

Another reason why this outfit works so well? The fit is spot on!

The sleeve length hits at the wrist bone and the shoulder seam is right at the top of the shoulder. 

Remember, you can buy clothing items in the best colors and made from the most luxurious materials. But if the fit is off, it instantly downgrades the outfit and your confidence. Don’t settle for something that just “sort of” fits. 

And if needed, invest in tailoring! It’s an extra step that can change your life.

Cashmere Turtleneck

Bloomingdale's cashmere turtleneck for female CEO's winter closet

Product by C by Bloomingdale’s Cashmere, shop here.

Our second essential for being a best-dressed woman CEO during the winter is a cashmere turtleneck. Cashmere is another one of those miracle natural fibers. It keeps you warm without adding extra bulk to your look. Plus, it’s incredibly soft and surprisingly durable. 

Buy a quality cashmere sweater and take care of it and you’ll have it for a lifetime.

One brand we love for cashmere is C by Bloomingdale’s. It’s accessible yet well-made. We especially love this turtleneck from their line because of the wide variety of colors it comes in.  

From joyful jade to a cool grey, you’re sure to find the right pick for your style preferences.

Style Tip: Make sure you invest in core colors before you buy a pop of color! Having knits in black, grey, white, and navy means you’re setting yourself up to have versatile, easy-to-mix-and-match outfits. 

Once you’ve got that strong foundation, then you can play with bold colors and patterns.

How to wear:

Not sure how to style a women’s turtleneck? Let’s go with a power casual dress code

Pull on your turtleneck and tuck it into a pair of trousers. We recommend straight or wide-legs for a contemporary silhouette. 

Complete your ensemble with a belt and boots. We prefer a thin belt for subtlety, and an ankle boot to strike that balance of practical and stylish.

A Midi Skirt

Kobi Halperin midi skirt for female CEO's winter wardrobe

Product by Kobi Halperin, shop here.

Our third winter must-have for female professionals and CEOs is the midi skirt. 

Skirts don’t get their time to shine that much when it comes to workwear. Pants are the norm for so many women and offices. But, if you like having something flowy, and feminine, yet polished in your arsenal, give the midi a try.

We prefer this style way more than the old-school pencil skirts that used to dominate corporate offices. A midi gives you the length you need for most dress codes and the coverage you crave during cold weather.

On top of that, there’s something about dresses and skirts that just look more styled. Even though it’s easy to throw on, you somehow look like you put more effort into your appearance. 

Go with an a-line style like the Kobi Halperin piece above and you’re also much more comfortable than you’d be in trousers thanks to the airy silhouette.

How to wear:

We recommend giving midi skirts a wintertime twist with a pair of tall boots. Knee-length or calf-length boots protect your legs from the frigid air while looking trend-aware. 

Not sure what material of boot to go for? Try a leather or leather-like set for a cool, even edgy vibe. Or go cozy with a suede or matte-finish option. 

Looking for more ways to style your wardrobe with CEO clothing this winter? Check out Next Level Wardrobe’s women’s styling services. We use our style system to makeover your closet, simplify shopping, and create the personalized wardrobe of your dreams. Say goodbye to stress and say hello to dressing well.

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.

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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.

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