Stylish Outfits for Your Real Life Holiday Events & Gatherings

With Thanksgiving behind us it’s time to get serious about what we’ll wear to the holiday events and gatherings on our calendars. Maybe you, like me, will mainly enjoy casual gatherings with family and friends. That said, I’m looking through local options today to schedule something festive and special for James and me to do soon so that I can dress up a little. For me it’s important to go “out on the town” occasionally to foster that sense of celebration and joy this season deserves. But regardless of how you are celebrating Christmas and the New Year, I’ve got a wide assortment of stylish outfits for your real life holiday events and gatherings to inspire you.

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We’ll start with the dressier outfit ideas and work our way to the most casual and comfy options for cozy celebrations at home. I’m showing only one photo of each outfit, but if you’d like to see more and learn fit information, click through to the original blog post linked in the caption of each photo. I’ve asked my assistant to only include outfits in which most items were still available in at least a few sizes, so you should be able to shop most of these looks. That said, I hope this post serves as style inspiration for you to reach into your closet, too.

Style Inspiration for Your More Elegant Events and Gatherings

An elegant but simple frock will help you feel festive and beautiful. Others may not be as dressed up, but that’s okay. You’ll never look out of step at this time of year if you add a little sparkle to your outfit. Jacquard fabrics are really having a moment this year. Isn’t it so interesting that even fabrics come and go in popularity? But this emerald mirasol jacquard Adelaide dress is truly timeless, so you’ll be wearing it again in years to come.

The woodbine satin Bellamy dress feels elegant and special. Don’t forget to accessorize your dress with a couple of pieces of strategically chosen jewelry. Carry a pretty clutch and wear some metallic shoes to keep your look festive from head to toe.

Even a “Sunday dress” from your closet can be made to feel more special with metallic shoes and a pretty clutch. But the Jude Connolly Delphine gilded Jude cloth dress above would make a lovely addition to your special occasion wardrobe.

PRO TIP: This is a great time to wear your finer jewelry, if you choose. Don’t feel the need to fill a neckline with a large necklace. You can add the shine elsewhere. And most of these outfits are special enough on their own without going overboard on jewelry.

Of course you could also wear a skirt instead of a dress. The Gabbie red two-piece midi dress above is actually a dress worn with a sweater. It also comes in olive and navy combinations. This is a nice option if you’re concerned about being warm.

PRO TIP: If you do choose to wear glitzy of significant fashion jewelry, keep it to one or two significant pieces. A chunky bracelet with rhinestones or glittery earrings are enough to add the shine you desire. Remember to draw the focus to your face!

The Hensley gold pleated midi skirt comes in silver and green, too. It does run small. I had to size up to a large in this one. But this is a skirt you can wear multiple ways for different holiday events and gatherings.

If pants are your preference, I have some style inspiration for you, too. You could opt for something velvet and flowy, like the velvet Nicolette pants below. Top them with the coordinating Essie velvet jacket (also available in green or blue) for a head-to-toe look. Or wear them with a favorite cashmere sweater for mixed textures.

Or you could wear more tailored velvet pants (available in more colors and a beautiful print) with a looser fitting top, like this gorgeous gold Noelle button down shirt. And a pretty oversized button-up shirt from your closet might work here, too. Of course you could also top the slim fit pants with a different tank. So these give you great versatility.

Don’t forget to consider your outerwear when selecting a special outfit. Investing in a beautiful coat or jacket that you can wear for special occasions will serve you well throughout the years. I love the faux fur coat from Tuckernuck above, as well as their shorter version. But another great place to look for remarkable jackets and coats is Frances Valentine.

Style Inspiration for Special Gatherings

We don’t have to wait for an invitation to a glitzy event to dress up a little for the holidays. I like to look a little “extra” this time of year even when I’m attending casual events and gatherings. My motto is, “Don’t wait for a special occasion to dress up; you bring the special to the occasion!”

You’ll look smart and festive, but still appropriately casual in a fun dress and boots combo. Whether you opt for a smart sweater dress or something like this plaid Delise maxi dress (limited availability in just a couple of sizes), you’ll feel just a little more party-ready for that special gathering.

I would not hesitate one minute to wear the velvet pants and cardigan sweater combination above to a holiday gathering of any kind. In fact, this is probably the outfit I will wear when we eat out with our church family or if James and I go out for a special lunch. Remember, at this time of year you have “permission” to wear velvet, metallics, sequins and feathers any time of the day!

PRO TIP: You certainly do not have to wear red or green to look festive at this time of year. But obviously those colors are a nice nod to the season. Wear the colors you feel your best in. But consider a brighter shade or maybe add a little sparkle to your outfit.

Begin your pants outfit with great trousers. Whether they’re velvet, plaid, corduroy or satin, a special pant with set the tone immediately. Then add the type of top that makes you most comfortable – sweater, silk blouse, plaid shirt, or festive sequined top. If you “go wild” with your pants, keep the top a little more conservative. Or if you opt for classic black slacks or everyday brown cords, wear something a little more festive up top.

I’ve got more great outfits from Talbots that are perfect for your holiday events and gatherings in the video below. Just click to watch!

Let’s talk about those “ugly sweater” parties. You don’t really have to wear something ugly, you know. But this is the time to wear a sweater that is, let’s say, a little more kitschy.

My kitschy Christmas sweater above is no longer available, but you’ll find similar options here. That said, they’re going fast everywhere. Ugly Christmas sweaters are popular you know! And again, I don’t think this sweater is ugly at all. But it’s definitely a little more playful than I’d probably wear otherwise.

And remember, those velvet (or plaid or satin, etc.) pants you purchased for that one special event can be repurposed so many ways for multiple looks. I’ll be wearing mine over and over!

Style Inspiration for Casual Events

Of course there are days when you just want to wear jeans. Even then you can dress up a little special by adding a pretty top and jewelry.

These are the types of outfits I like to wear when I gather with any group of friends and exchange gifts. I’ve got some great ideas for gift swaps in the video below.

Yes, you can simply top your jeans with a pretty closet in your regular rotation. But I like to have one or two with some glitz and glimmer on hand.

These types of holiday outfits are perfect for:

• baking cookies with grandkids
• making holiday deliveries
• visiting a friend at a senior center or hospital
• exchanging gifts with friends
• volunteering
• a casual church event
• a school musical performance

Outfit Inspiration for Cozy Holiday Time at Home

Especially if you are visiting in someone else’s home or hosting in your own, it’s smart to think ahead to how you’ll dress for those cozy, casual moments. Whether you’re cuddled up to watch a holiday movie, wrapping gifts or cooking a big breakfast together, these are ideas for how to look festive, comfortable and appropriately pulled together.

Even when I travel to visit friends and family or spend time at a resort, I pack a loungewear set like the one above. These are perhaps my favorites, but you can see others I enjoy in this blog post. I like to wear a bralette and/or a camisole under mine, especially when I’m around other people.

Of course you’ll also want to put some thought into the sleepwear you’re wearing during the holidays. I love the Soma Cool Nights pajamas. I like to purchase the long sleeve top, tank and pants so I can adjust to the warmth level in the home.

I hope this little bit of style inspiration has been helpful to you. Let’s get dressed for the holiday! Remember, don’t wait for a special occasion. You bring the special to the occasion!

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