If you haven’t figured it out yet, I love Christmas. My whole life has been consumed by the holidays and everything festive. From my home decor, to my food (check out 15 Christmas cocktails to try), my wardrobe, and my calendar – if it isn’t festive then it isn’t happening this month.

I grew up loving this time of year, and now as an adult the love is still there! There is just so much to do during this time of year – Check out my Ultimate Holiday Bucket List! With so much going on, sometimes finding the perfect outfit is too much to think about. Enter me, Miss. Holly Berry herself and I have pulled together outfit ideas for any and every winter activity!

What To Wear To Every Winter Activity

Ice Skating

Puffer + Colorful Scarf

Call it cliche but ice skating is THE quintessential winter activity. Makes for the perfect date night, or friends activity. Personally, I have never been ice skating if there are any takers out there, please let me know! But please know you will have to hold on to me because I can barely walk on normal ground, let alone ice.

BUTTTT, a puffer jacket is the perfect outwear option for this. They are sporty, but will keep you warm. Of course add a bright colored scarf to keep you cozy and looking cute. Make sure you wear a warm pair of thick socks too! The last thing you want is cold toes and blisters from the skates. Don’t forget your mittens, but hopefully someone’s hands are keeping your fingers warm!

Holiday Party

Leather Dress + Sparkle Booties

Tis the season for holiday parties. Whether it be your office holiday party, a girls night holiday party, or any event in December my rule of thumb is always sparkle and always a red lip. You don’t have to go full out glam and sparkle if that isn’t you (it is me thought 100%). Adding a touch of sparkle to your accessories is a safe way to go. From shoes, earrings, tights, and/or your purse there is always an easy way to add a little sparkle. The red lip however is nonnegotiable. The holidays is one of the only times where I rock a red lip, and I will continue to do it at every event I attend in December.

Christmas Market

Festive Jacket + Beanie + Turtleneck

One of my favorite wintertime activities is to visit a German Christmas market. Here in Chicago we have the Christkindlmarket and it is always a good time. Grab a mug of mulled wine and a plate of potato pancakes and I am one happy gal. I love walking around the little houses and just taking everything in. One of my bucket list items is to visit the Christmas markets in Europe! One day!!

Christmas Show

Red Dress + Statement Headband

Whether it is a musical, comedy show, the Nutcracker anything that is festive and requires a little dressing up – I am here for it! I would go bold with a classic red holiday dress. A lot of women shy away from red because it is so bold, but that should be the reason you wear it. I feel the most confident when I am wearing red.

The perfect holiday accessory is a statement headband – embellishments, pearls, beads, rhinestones – anything! They instantly elevate any look and add a level a chic. I personally think they are so fun and give off total Queen B vibes! I wear headbands all year round, but especially during the holidays!

Looking at Christmas Lights

Christmas Sweater + Leather Leggings + Earmuffs

One of my favorite holiday traditions is looking at all the Christmas lights, in my family we call it light night! We pack the car with blankets and hot chocolate and go drive to a bunch of light displays in town. Whether you are viewing them from the warmth of your car, or braving the cold and venturing outside you will need to dress cozy and warm!

I think I am in my ear muffs era because I have been wanting to purchase every pair I come encounter with! I have limited myself to just one (these hot pink ones), but I think they are just too cute! Throw on a pair of leather leggings and a festive sweater and you are good to go!

Movie Night

Holiday PJ Set + Slippers

Whether you are watching The Grinch, Rudolph or a Hallmark movie, you ought to have at least one holiday movie night. No better outfit than festive pajamas! Whether it be a set, a onesie, you pick your poison! Turn on your Christmas tree, light a holiday candle and cozy up for a Christmas classic.

Happy Holidays!