What to Wear? | Holiday Party Dresses & Winter Wedding Guest Dresses

The holiday season is upon us, and it’s time to plan your holiday party look! Of course, that’s not all! We’re also seeing all those postponed 2020 weddings happening left and right! Holiday parties and winter weddings can be enchanting, but the weather can be unpredictable, so determining what to wear can be a challenge.

Special occasion dresses this time of year typically feature longer gowns and sleeves, higher necklines, rich colors, and heavier fabrics. Don’t worry, though! This doesn’t have to mean you’re restricted to boring or uncomfortable choices! We’ve rounded up the very best holiday party dresses, and winter wedding guest dresses to wear this season, plus the scoop on how to dress for any special occasion.

What to Wear to a Holiday Party or Winter Wedding

When shopping for special-occasion looks, I think it’s important to think about possible future uses for your outfit. I recommend splurging a little and buying an outfit you can wear to more than one event. Just tell your husband it’s an investment, and you’ve amortized it over time. 🤣 (If you pull out that fancy word, he’ll be so stunned 😯, he’ll probably just nod. Trust me on this one! 😁)

There are plenty of affordable retailers to shop with beautiful, budget-friendly options. Some of my favorites are Nordstrom and Nordstrom Rack, J.Crew, Dillard’s, Macy’s, and even Amazon. (Probably my favorite special occasion dress designer is Mac Duggal. Check out his dresses HERE.)

If you have a really busy event season coming up, you could also consider renting your outfits from Rent The Runway. It’s a fantastic service that allows you to wear something new to every event without that only-wore-it-once guilt!

Consider the Dress Code, Venue, and Time of the Event

Before choosing your party or wedding outfit, make sure you double-check the dress code and venue so you can plan accordingly. Additionally, the time of the event will offer insight into the level of formality you can expect. For example, afternoon weddings may call for a casual dress and denim jacket, while a holiday party at an upscale hotel may call for a sleek jumpsuit or evening gown.

Black tie events will allow you to bring the drama! Think rich silks, dramatic, long-sleeved dresses, and statement accessories. Cocktail parties and cocktail weddings are the easiest to dress for—and they leave lots of wiggle room for personal style. (Think unique prints and vibrant colors.)

Casual weddings seem to be in style this year, with many couples opting for outdoor or non-traditional venues. For those, you might be able to dress up pieces you already own, or you might want to get something new that would be easy to repurpose in the future.

Wear Rich, Deep Hues

At the risk of stating the obvious, pastels are great for spring and summer, but they look out of place this time of year. Instead, consider rich jewel tones like sapphire, emerald, garnet, mustard, burgundy, plum, or fuchsia. Of course, black is always a favorite, but let’s be honest—it’s not very original! Also, depending on your skin’s undertone, it may wash you out somewhat—so be careful.

Wear Textured Fabrics

This time of year, texture is a fabulous element to incorporate into your look. Try fabrics you wouldn’t typically wear in the warmer months! Think velvet, brocades, metallics, satin, lace, fur. Also, consider embracing subtle features like bows, ruffles, sequins, and unique hems. Feel free to explore bolder prints, like textured florals or polka dots, If it’s appropriate for the occasion.

Embrace More Coverage

One of my favorite things about dressing for cooler weather is that I get to wear outfits with a little more, um, coverage! (I’m pretty modest!) Some of the best looks we found will not only cover your upper arms, but will also stop you from getting goosebumps! You want to be warm enough that you can be present and focus on having fun! Now is a great time to play with assorted necklines and unique sleeve cuts!

Also, don’t rule out a jumpsuit for a holiday party. It can be repurposed as a fun winter wedding guest outfit in early 2022.

Add Cool Weather Accessories

Now that you’ve found your look, all you need to do is add some heels, darling accessories, and perhaps grab a dressy coat, cape, or shawl to keep you warm. You might want to opt for a block heel, low kitten heel, or flats to ensure you stay comfortable for the duration of your event.

Closed-toe or peep-toe heels are most logical if it’s chilly, but depending on where you live and the event, you might be able to wear an open-toe sandal. When it comes to accessories, a clutch bag is the perfect option to fit all your essentials and still look stylish. Add a wrap or bolero over a dress to keep you warm and complete the look. If you feel you might be cold, opaque tights or sheer hosiery are a great option for a little extra warmth.

I’ve also got you covered when it comes to makeup and hair! Check out the articles below for all the makeup over 50 tips you need to know!

A Pro Answers Your Biggest Makeup Over 50 Questions

What I Learned When I Took A Professional Makeup Lesson

5 Midlife Makeup Mistakes You May Be Making (And How To Fix Them)

5 Ways To Figure Out Your Skin’s Undertone & Your Best Makeup Shades

Tips For Aging Lips  | What You Can Do About Thinning, Lines, and Dryness

You’re All Set!

Now that you know exactly what to wear to your big event, it’s time to shop! We rounded up all the best dresses, jumpsuits, and accessories for your next special occasion in one convenient place. All that’s left is to have the time of your life! (And that one’s all on you!) 💃🎉🥂