Holiday Style Guide 2020

Holiday Style Guide 2020

Holiday Style Guide 2020

Today we are going to be chatting all about the top styles to get your hands on for the holidays!  In today’s holiday style guide, I am going to break things down into different sections, featuring my holiday must haves and the many ways that you could wear them throughout the holiday season.  When deciding what to fill my closet with while shopping for “seasonal clothing” I like to be able to interchange basic pieces that I can wear repeatedly in multiple ways.  With that being said, let’s get this party started!

2020 holiday style guide.


Who doesn’t love a great cardigan?  They are cozy and can be worn dressed up or down.  I am obsessed with this one and the amazing button details.  A cardigan is always easy to pair with a basic tee and jeans OR you can pair it with a cute dress if you want to be a little more on the fancy side, but don’t want to freeze to death.

cardigan | jeans | boots 

Cardigan style guide tip:  If wearing your cardigan with a dress be sure to pick a more fitted cardigan so you do not lose your shape.  Also, generally longer cardigans look better with dresses because they lengthen your silhouette and don’t cut you off in all the wrong places.   


Give me all the sweaters! I have always been a big fan of a beautiful sweater, but this year the sweater game has stepped way up!  We are loving the high neck sweater trend and the slouchy sweater that isn’t too chunky to do a cute front tuck.

A holiday style guide 2020

sweaters | pants | boots 

Sweater style guide tip:  Pick sweaters that flatter your neckline.  Be careful not to pick a sweater that is too bulky or it will make you look heavier than you actually are.  We have an amazing selection of lightweight sweaters HERE.


Flannel is a classic material style that I don’t think will ever totally go out of style.  I love that you can layer with flannel and that most flannel tops are flattering when you wear them both, buttoned up and unbuttoned.  A good buffalo check flannel is the PERFECT holiday top.  Not to mention, flannel is extremely warm.  This is a huge bonus in my book!

flannel shirt | shirt | pants | boots 

Flannel style guide tip:  Pick a flannel top that you can wear with both black bottoms and denim bottoms.  Pick flannel colors that you are comfortable in and make sure that the flannel pattern you pick is flattering to your body.


The boot trend is absolutely killing it this holiday season!  Again, we love that boots easily dress up an outfit or dress it down depending on what style of boot you choose.  We can’t get enough of the lace-up boot trend that is growing at a rapid pace.  A good boot can be worn with jeans and a t-shirt or a dress.  One of our favorite holiday outfits is to wear a dress, tights, and a good boot.  You will be a showstopper for sure!

boots | sweaters 

Boot style guide tip:  Pick a staple black boot and a staple brown or taupe boot for the holidays.  If you have a good boot in each of these colors, then you will always have a pair of shoes to wear with any holiday outfit!  Be smart when boot shopping and make sure that you pick boots that will go with the different outfits you have in your closet. 


The beanie look is a look that is getting more and more popular.  I think it is because washing your hair is getting less and less popular (I mean who has time for that).  So basically, the beanie trend allows you to look cute AND not have to wash your hair one more day.  Who wouldn’t cash in on this holiday look?  These beanies with poms are just about the greatest things since sliced bread!


Beanie style guide tip:  Leave your hair down with your beanie.  People will think that you put a lot more effort than you actually had to into your holiday outfit!


Nothing screams, “holiday party” like a dreamy dress.  If you’re going somewhere fancy then you will obviously want to wear a more elegant dress, but I love pairing a knee length dress with a cute pair of boots for the perfect day-to-day look!  These boots will go perfect with just about every dress in your closet!

shirt | dress | boots 

Dress style guide tip:  Pick a dress that gathers at the smallest part of your waist.  You will be amazed at how flattering this will make the dress on literally every single body type! 

Matching Sets

I think that we can all agree that 2020 has brought out the crave for comfort in all of us!  What is the answer to comfort and cute all wrapped into one outfit?  Matching sets!  It would be fraud if I didn’t include my love for matching sets in our holiday style guide.  I love them and I know that you guys do too!  Whether it’s a matching skirt/shirt set, or a matching jogger/sweater set you need a set in your life.  They are so dang cute and will allow you to enjoy a few extra holiday goodies with ease.

matching set | boots 

Matching set style guide tip:  If possible, pick a neutral colored set so you can mix and match your top and bottoms with other top and bottoms if you ever feel like switching things up.  Also, pay close attention to suggested sizing details.  I have found that a lot of matching sets tend to run on the smaller side. 

Whether you are traveling or staying home for the holidays this year, I hope that this holiday style guide can take the stress of not knowing what to wear off your plate! For more style tips you can visit THIS POST.

Make sure to check out our Love Olive Co. holiday releases every week right HERE. We have so many good new releases lined up that you will not want to miss!  Happy holiday shopping friends!