Holiday Wardrobe Essentials: Must-Have Outfits for Every Festive Event

The holidays are approaching, and your schedule is likely getting busier and busier by the day. With so many events on the horizon, it can be tough to figure out what to wear for each occasion. Never fear, the Masseys style experts are here with outfit ideas for every festive to-do! From shopping for gifts to celebrating with coworkers, here’s what to wear to every event this holiday season.

Picking Out a Christmas Tree

Whether your family prefers to browse the pre-cut trees sold by the local little league or hiking into the forest to chop one down yourselves, staying warm is important. A long puffer coat and a pair of insulated winter boots can go a long way to make this holiday tradition much more enjoyable. We also recommend a nice, steaming cup of hot chocolate to keep your hands warm. Trust us, we’re professionals. 

The key to staying comfortable when doing outdoor winter activities is layering. Depending on the day’s forecast, you might want to wear warm leggings and an athletic top under your outfit to help keep body heat in. Other layers like flannel tops and pullover sweatshirts are also great because you can easily throw them on or off to customize your level of warmth. When holiday decorating takes you from inside to outdoors and back in again, you can easily add and remove layers to stay perfectly comfortable all day long. 

Holiday Shopping Spree

Sometimes the best way to knock out your mile-long holiday shopping list is to go on an all-day shopping spree. For this marathon, you need shoes that keep you comfortable even after hours on your feet. Skechers sneakers have a lot of different comfort technologies, such as Skechers Air-Cushioned Memory Foam and Arch Fit insoles, that help reduce foot fatigue on your busiest days. Plus, they’re super stylish! 

Pair your favorite sneakers with comfy joggers and a lightweight tee to create a sporty look that’s perfect for hitting the shops. When you get home, whether you immediately crash on the couch or go straight into gift-wrapping, you’re already in a comfortable outfit that’s just right for the job. 

Cookie Exchange With Friends

Cookie exchanges are a great way to catch up with friends during the holiday season while also enjoying a variety of tasty treats. While this affair is often more casual than other holiday events, it’s still a great opportunity to put together an outfit full of festive flair. Break out the festive colors and match them to statement boots and holiday-inspired jewelry. Got an ugly Christmas sweater? Now’s the time to wear it! 

To keep your outfit on the nicer side, pair your sweater with denim jeans in a darker wash and a cute ankle bootie or pump. The right shoe can do a lot to set the tone of an outfit and make casual pieces feel more formal. Jewelry is another great way to give your look a formal touch.  

Office Holiday Party

The dress code for a holiday office party can vary from company to company and can depend on the venue and theme of the event. Look for flyers or emailed invitations for clues on how to dress. An ugly sweater contest is a good sign of a more casual vibe, while drinks at a nice restaurant will require something more formal. If you still aren’t sure, don’t be afraid to ask around the office to see what your coworkers plan on wearing to the event. 

You can’t go wrong with a professional blouse featuring a festive color scheme or pattern, fitted slacks or a pencil skirt, and comfortable pumps. This outfit doubles as a stylish work outfit, so you can go right from your desk to the holiday festivities with no need for an outfit change. Need something a little more formal? Masseys has a wide variety of dresses and suit sets to choose from, plus pumps to go with everything in your closet. Not sure how to pick the right heel? Check out our blog post “How To Find Your Perfect Pump” once you’re done here for our tips and tricks! 

School Holiday Recital

When it comes to the kids’ holiday concert or recital, you’re likely more worried about what the little ones will be wearing on stage than your own outfit. Don’t worry, we have your back! Consider it our holiday gift to you (in addition to all of the deals and savings you’ll find all holiday season long).  

This is another instance where you can look to the venue to determine what to wear. If the concert is taking place in the school cafeteria or gym, a nice sweater, dark denim pants, and ankle boots should be just fine. If the event is in an auditorium, church, or theater, opt for a dress or blouse and skirt duo. Not sure how formal to go? A sweater dress is the perfect in-between look. You can easily dress this look up or down with the right shoes and jewelry.  

Seeing a Festive Play or Ballet

Many families include a trip to the theater to see A Christmas Carol or The Nutcracker in their list of holiday traditions. This is not only a great opportunity to support your local performing arts program, but also a fantastic excuse to get all dressed up! That formal look in your closet that never gets worn? Now’s the time to get it out! 

Elegant, long-sleeved dresses are perfect for a trip to the theater. Embellish with sparkling jewelry and stand-out heels to create a look that will make a statement without stealing the show. Add a gorgeous faux fur coat and you’ve got a glamorous ensemble worthy of a grand performance.  

Opening Presents with the Family

Finally, the big moment comes. You’ve spent the past several months making lists, checking them twice, wrapping and hiding gifts, and now it’s time for the big reveal. What do you wear for such a special occasion?  

If your family is the type to open presents immediately after waking up on Christmas morning, soft and stylish pajamas are a must. These will keep you cozy and warm through the long winter’s night while also looking great in any photos snapped during present opening. Need a little extra warmth? Wrap up in a plush bathrobe and slip on your warmest slippers. Maybe, if you’re lucky, you’ll find one of these winter essentials under the tree waiting for you! 

Tis the Season for Festive Fashion

The holidays give us a ton of different opportunities to dress up and show off our style under the colorful lights. Whether you’re attending a casual gathering or a glamorous holiday party, you’re sure to look your best with these outfit ideas in your back pocket. Don’t feel like you have to follow our recommendations word for word, though! Put your own personal spin on these looks to transform them into unique looks that are all your own. We’d love to see what festive looks you can create with your Masseys fashion finds, so be sure to tag us in your photos on Facebook and Instagram. Happy holidays! 


Which of these looks will you be rockin’ around the Christmas tree this year? Let us know in the comments below, and then tag us in your sparkly outfit pics on Facebook and Instagram.   

Tags: Casual, Dresses, festive, Formal, holiday, outerwear, outfit ideas, outfit inspo, sleepwear, sweaters, Winter Fashion

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