The 12 Days of Entrepreneur Holiday Style: : Festive Looks for Fabulous Women in Business

The holiday season is upon us! 🎄✨ And as entrepreneurs, our December calendars are brimming with opportunities—client meetings, networking events, holiday mixers, and maybe even a moment to celebrate our own hard-earned success (cheers to that! 🥂). If the thought of wearing red, sparkles, glitter and sequins makes you squirm in your cozy sweats, this post is for you!

But here’s the thing: what you wear to these occasions matters. Dressing well doesn’t just make you look good; it’s a confidence booster and an incredible way to leave a lasting impression. So, to keep you feeling festive and professional, I’ve created The 12 Days of Entrepreneur Holiday Style—a guide to looking polished, powerful, and holiday-ready!

Presenting 12 style options without looking like the Christmas Elf threw glitter bombs all over you!

Day 1: Power in Plaid

Plaid is your secret weapon this season! It’s festive enough to feel like the holidays but polished enough for business. Pair your classic plaid with a sparkly skirt for an unexpected feminine twist. Or wear plaid in an unexpected way- a coat! Layer it over a dress and chunky boots for interest. A feminine pink plaid will go beyond the holidays when worn with dark denim and understated accessories.

Day 2: Statement Earrings to Steal the Show

Who says Zoom calls can’t be festive? A bold pair of statement earrings can elevate even the simplest outfit. Metallics, jewel tones, or sparkly designs—anything that adds a little holiday magic will do the trick. We won’t tell anyone that you are wearing Christmas pj’s on the bottom, as long as you don’t get up from your seat!
Balance bold earrings with a sleek hairstyle like a low bun or straightened locks for a sophisticated vibe. And don’t forget to add a bold lip in your best color!

Day 3: Velvet Vibes

No Sparkles, no problem! Velvet adds warmth, elegance and holiday cheer in a very understated way. Velvet says luxury, elegance, and just the right amount of drama. Whether it’s a blazer, a chic sheath dress, a pair of velvet trousers or simple accessories like hair bows this fabric works wonders for holiday events.

Day 4: Red Alert: The Confidence Booster

Ready to make a statement? Red is the color of confidence, and it’s perfect for the season! Wear it as a bold dress, a pop of color in your scarf, or even a pair of red pumps. Red is a high-energy color that signifies power, confidence, and boldness. Red increases physical energy and mental alertness, which can boost the confidence needed to take action toward business goals.
Style Tip: Not into bold colors? Add red through accessories—a leather belt, a structured bag, or even lipstick can do the trick!

Day 5: Metallic Accessories for a Subtle Sparkle

Metallic shoes, belts, or clutches are like little sprinkles of holiday cheer for your wardrobe. They add just enough sparkle without going overboard.
Style Tip: Keep your outfit neutral (like a sleek black dress or white blouse) to let your metallic accessory stand out.

Day 6: Cozy but Chic Layers

When the weather outside is frightful, but your schedule is packed, chic layers are your best friend. A polished coat, a cozy sweater, and a statement scarf can keep you warm and stylish.
Style Tip: Choose a monochromatic palette (like camel or winter white) for a look that’s effortlessly chic.

Day 7: Power Pants with a Festive Twist

Wide-leg trousers in festive shades like emerald green, burgundy, or even gold bring the perfect mix of confidence and holiday charm. Look for denim that has embellishment like rhinestones, sequins or pearls. Pair with a basic white tee and a classic cropped jacket.
Style Tip: Pair bold pants with a fitted blouse or turtleneck to balance the silhouette. Bonus points for a skinny metallic belt!

Day 8: The Festive Midi Skirt

Midi skirts are a holiday classic, and they’re endlessly versatile! From pleats to sequins or lace details, they’ll take you from a client lunch to a holiday party with ease.
Style Tip: Pair with knee high boots and a fitted sweater for a modern, boss-approved look.

Day 9: Blazer as the Hero Piece

Blazers are the instant authority makers in your wardrobe. Don't put them aside just because it is the holiday season. Pair them with the simplest of tops and bottoms and let the blazer do the talking.
Style Tip: Keep the rest of your outfit simple to let the blazer shine. Add heels for extra confidence or pair with sneakers to keep it fun and playful.

Day 10: The Power of Prints

Winter florals, abstract holiday-inspired designs, or even a subtle festive plaid can add personality to your look while keeping things professional.
Style Tip: For a polished effect, choose prints in colors like black, green, or burgundy or the unexpected silver.

Day 11: Winter White Elegance

There’s nothing more chic than winter white. Tailored trousers, a cozy knit sweater, or a sleek midi dress in this hue make a subtle yet powerful statement.
Style Tip: Add gold or pearl accessories for a hint of holiday sparkle.

Day 12: Sparkle & Shine with Confidence

Let’s end the season with a bang (and some sequins)! A sequin blazer, glittery top, or metallic skirt can be festive while still looking professional.
Style Tip: Pair sparkle with classic pieces—like a well loved pair of jeans or classic ankle boots—for a balanced look.

The holidays are a time to celebrate your success and showcase your style. Whether you’re rocking plaid, velvet, or a little sparkle, remember: your outfit is an extension of your brand. Dress in a way that reflects your confidence, creativity, and entrepreneurial spirit.

So, which of these holiday looks are you most excited to try? Let me know in the comments—I can’t wait to see you sparkle!

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