Holiday Style Guide: How to Strategically Plan Your Outfits for Every Festive Event

The holiday season is a flurry of parties, gatherings, and celebrations, each with its own unique vibe. As your personal stylist and wardrobe strategist, I'm here to guide you in planning a holiday wardrobe that leaves you feeling confident, stylish, and stress-free at every event. From cozy family dinners to glamorous New Year’s Eve parties, let’s make this holiday season your most effortlessly chic one yet.

1. Plan Your Event Calendar

To start, we’ll map out every event you plan to attend, categorizing them by dress code—casual, semi-formal, formal, or themed, or by individual events. By planning ahead, we can create targeted outfits for each, saving you time and minimizing stress.

2. Invest in Versatile Staples

I’ll help you select key pieces that can transition effortlessly across different occasions. My goal with every piece is to choose pieces you can wear well beyond the holiday season, and pull out again year after year:

  • A Luxe Blazer: Perfect for elevating jeans or adding polish to dresses, and can be worn well beyond the holiday season.

  • Statement Accessories: Add sparkle and transform a basic look into something extraordinary.

  • Classic Footwear: Comfortable and chic shoes like velvet pumps or elegant flats that work with various outfits.

Shop the Holiday Edit

Shop Additional Holiday Looks

3. Customize Looks for Each Event

Together, we’ll style each outfit to fit the unique setting and vibe of your events:

  • Office Holiday Party: A tailored dress or sleek trousers with a chic blouse and festive accessories.

  • Family Gatherings: Comfortable yet stylish, like a cozy cashmere sweater paired with a sequin skirt

  • Formal Events: A show-stopping gown or sophisticated jumpsuit, paired with bold accessories for a touch of glamour.

  • Casual Friend Meetups: Trendy pieces like a velvet top and high-waisted jeans or a sequin blazer over a simple tee.

4. Layer Wisely for Winter

Staying warm doesn’t mean sacrificing style. I’ll show you how to layer with sleek coats, textured wraps, or faux fur stoles that enhance your look without overwhelming it.

5. Play with Seasonal Trends and Colors

This season is the perfect time to embrace festive colors like emerald green, burgundy, gold, and silver, as well as textures like velvet and metallics. We’ll find what fits your personal style and makes you shine.

6. Work with a Personal Stylist for Stress-Free Holiday Dressing

By working with me, you’ll enjoy a wardrobe that’s cohesive, versatile, and tailored to your unique needs. I’ll take the guesswork out of what to wear, so you can focus on making memories.

7. Create a Holiday Capsule Wardrobe

We’ll build a capsule wardrobe of curated, mix-and-match pieces that give you endless outfit possibilities without clutter. This approach ensures you’ll be ready for any invite with minimal effort. ( PS a holiday capsule wardrobe will be available to purchase the week of November 18th)

8. Elevate with Accessories

The right accessories can transform any outfit. We’ll handpick scarves, belts, jewelry, and handbags to add the perfect touch of holiday cheer or sophistication.

9. Shop Smart and Mindfully

No more last-minute shopping stress. I’ll identify any wardrobe gaps and either source the perfect pieces or take you shopping, ensuring every selection is high quality and fits seamlessly into your style.

10. Be Prepared for the Unexpected

We’ll also create a few “backup” outfits for any surprise invitations, ensuring you’re always ready with something chic and appropriate.

Make This Holiday Season Effortlessly Chic

The holidays are meant to be joyful, not stressful. With a bit of planning and the expertise of your personal stylist, you can make every holiday event an opportunity to shine. Ready to elevate your style? Let’s start planning your personalized holiday looks!



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