The Gift of December: 12 Days of Christmas with Dymond’s Diary | Day Ten: Holiday Looks I'm Loving This Season

dymond phillips • December 23, 2025

Seven Easy Holiday Outfits For Every Festive Plan

I’m having so much fun with this series, and now it’s time to get into one of my favorite parts of the holidays… THE LOOKS.


Putting together the perfect outfit, doing my makeup, and getting my hair done is truly the quickest way to boost my mood. I love winter, but I especially love the holidays because the girls really show up with the looks. Christmas season screams boldness, sparkles, fur, texture, and anything a little over the top. Holiday parties are the perfect excuse to pull out that one piece in your closet you haven’t had a place to wear yet.


And the best part? You don’t have to do too much. You can mix flashy statement pieces with basics and still look put together. Sometimes all it takes is sequins, a great jacket, or a bold accessory to elevate the entire look.


Today I’m sharing seven of my go to holiday looks, no matter what kind of party you’re attending. This time of year, the invites stack up quickly; girls nights, office parties, bar parties, Christmas events, and New Year’s Eve festivities. I know it can feel overwhelming trying to figure out what to wear for everything, so I put together looks that are easy, stylish, and made up of pieces you might already have in your closet.


We’re already spending enough money during the holidays; gifts, Secret Santa, giving back, and everything else, so my goal is to help you save where you can. And if you do feel like grabbing a few new pieces, everything I’m sharing will be linked, easy to find, and under $50.

1,The Little (or Long) Black Dress

Everyone has a black dress in their closet; whether it’s sweater material, silk, cotton, or ribbed. The holidays are the perfect time to pull it out. Add stockings, a boot or bootie, maybe a slingback or pump, a red lip, and you instantly have a holiday look. You can even add a Santa hat or elf ears for something playful.


This look is for the girls who don’t want to do too much but still want to look classy. A black dress and a festive accessory works for an office party and a girls’ night. If you want a little razzle dazzle, swap in an animal print or colored boot or pump.

Black Skirt

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Black Mid Calf Boot

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2. Satin, Silk & Tulle

I love playing with texture, especially in the winter. Satin is one of my go-to fabrics because it instantly looks elegant. Satin pants or skirts elevate a look right away, and they can be dressed up or down, even styled with sneakers.


Mixing satin or silk with other textures like lace, metallics, fur, or leather makes an outfit feel intentional and fun. I also love a monochromatic look with different textures layered together.


And tulle isn’t just for kids. Long tulle skirts during the holidays are everything. Like sequins, tulle is the star of the show, so you can keep the rest of the outfit simple. A tulle blouse with jeans or a long tulle skirt paired with a tall boot is such a cute holiday look. Add gold or silver accents to make it festive.

3. A Good Blazer & Jeans

I live for a good blazer. It’s perfect when you want to look casual but still put together, especially for after work holiday mixers. Whether it’s a festive red blazer, classic black, or a patterned one, pair it with wide leg or skinny jeans and you have a look.


In the winter, I usually add booties and it never misses. If you want to take it up a notch, throw on a sequined cami underneath for a cute New Year’s Eve moment. The blazer is the star, so everything else can stay simple. And the best part? Blazers come in so many silhouettes and styles.

Sequin Pants

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Sequin Dress

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Black Bodysuit

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4. Sequins

The holidays are the prime time for sparkles. I love sequins year round, but during Christmas, they’re essential. Whether it’s sequined pants, a dress, or even shorts paired with stockings, this is the season to wear those “over the top” pieces.


Sequins are the main character, so everything else can be simple, basic shoes, a neutral bag, and you’re done. I love pairing sequins with a plain bodysuit because it looks like you did a lot when really the piece is doing all the work. And don’t limit yourself to black, colored sequins are just as fun. I've been loving the burgundy's I've been seeing lately.

5. Mini Skirt or Shorts

I used to hate shorter pieces, but I’ve leaned into them lately, in a tasteful way. I’m not saying walk around with your cheeks out. I’m saying, depending on your body type, a mini skirt with tights and a sweater can be really cute for the holidays. I usually pair mine with thigh-high boots.


Shorts aren’t just for summer either. Leather, denim, sequins, velvet, paired with a turtleneck or sweater, can easily become a holiday look. This one can go from cute to too much quickly, so I wouldn’t wear it to a work event, but it’s perfect for a good Friendsmas or girls night.

Pearl Cardigan

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Leather Leggings

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Black Bootie

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6. Leather

Leather is a fall and winter staple, but it’s also one of my favorite holiday textures. A leather dress, leather leggings with a sweater, or even leather shorts can work perfectly for festive events. I wore leather to a play last week and it was such a hit.


What I love about leather is the versatility. They even make beautiful animal print and colored leather now. My go to colors are black and burgundy, but brown leather is having a moment too. I love softening leather by pairing it with pearls for an extra touch.

7. The Christmas Sweater

You can’t go through the holiday season without a Christmas sweater. I wear mine to see Christmas lights, walk around the neighborhood, and casual holiday gatherings. I was invited to a holiday game night recently and I’ll definitely be wearing a Christmas sweater and jeans. Plus, they don’t always have to be red.


You can dress one up with heels or keep it casual with a flat boot or sneaker. I love this option because it’s comfortable. I usually pair mine with leggings or boyfriend jeans, and sometimes I’ll add a collared shirt underneath for an extra touch. Christmas sweaters also work for casual Fridays at the office, depending on your workplace and yes, you can even wear one with a skirt if you want to dress it up a bit.

The key to holiday dressing is having fun. Wear the pieces you’ve been sitting on all year. Dress up just to go to the grocery store. This is the season to step a little outside your comfort zone. Even if you’re just Christmas shopping, throw on your favorite party dress.


For me, adding flair to my style is part of the Christmas magic. I even find myself shopping differently this time of year, picking up pieces I normally wouldn’t. This is the season to explore, experiment, and express yourself.


Whether you’re headed to an office party, holiday mixer, movie night, Friendsmas, concert, or just taking yourself out for a bite to eat, I challenge you to put on an outfit that makes you feel your best. Clothes are a form of self expression. You don’t have to follow the status quo, and you don’t have to wait for the “perfect” moment to wear your favorite pieces.


This is the moment. Bring them out now!