
The merriest season is gearing up, and that means it’s time to start planning holiday outfits! Getting dressed up feels extra special this time of year. There’s something about the holidays that makes me feel especially excited about putting outfits together for parties and events. Everything feels a bit more buzzy and glowy, which makes it the perfect time to add a bit of glam and sparkle to your look!

I don’t know about you, but the very first thing I think about when I receive an invitation to an event is: what am I going to wear? I prefer to plan my outfits far in advance so there is no scrambling in the days leading up to the event. The holidays are already a busy time of year, and the last thing I want to feel before a fun party is stressed! That’s why I am getting a jumpstart on planning holiday looks now so that I will feel prepared and excited for the festive occasions on the calendar.

With that in mind, I am sharing 3 holiday looks that I think you will love, all of which are versatile and would be perfect for many holiday occasions! These looks are all from Sail to Sable‘s new holiday collection. I am a big fan of Sail to Sable year-round, but I especially love their holiday collections, and this one did not disappoint! Their designs are always classic yet fresh, and I’m obsessed with all three looks that I’m sharing today. Also, don’t miss my discount code towards the bottom of this post!
#1: Tweed Mini Shift Dress:


When this dress arrived, it was love at first sight! The details are truly stunning and even better in person. This tweed mini dress has a subtle metallic threading that gives the dress a little sparkle, yet it still feels classic and sophisticated and would be appropriate to wear throughout the entire fall and winter season. I particularly love the fringe details around the sleeves, the collar, and the pockets – it is giving Chanel vibes!
Where would I wear this dress? This dress works for any holiday occasion, but I think it would be especially perfect for a holiday work event, a dinner with girlfriends, or a holiday date night.
What would I wear with it? I love this dress paired with either metallic heels to bring out the details in the dress, or a classic black heel. If going with a black heel, I especially love this pair I just got in from Tuckernuck. The fabric is a grosgrain material and I feel like they should really hold up over time! My Bre clutch from Lucy Jane has proven to be the perfect clutch to pair with holiday looks. The bag has interchangeable charm adornments so you can perfectly style it with any look! For jewelry, I’m keeping things simple with my favorite lab-grown sapphire tennis bracelet and earrings (20ALEXANDRA for 20% off).



#2: Long Sleeve Mini Jacquard Dress:


I shared a try-on on my stories last week, and in it, I deemed this dress to receive the Most Fun Dress to Wear award! This mini has a fit and flare shape with a pleated skirt that has a bit of movement when you walk, truly making it the most fun little dress to wear! What I love most about this dress is that it is supremely comfortable – the top half is a comfortable cotton blend with sleeves, and the bottom half is a jacquard fabric with beautiful gold detailing.
Where would I wear this dress? This is another style that would work for a range of holiday occasions, but I particularly love the idea of wearing this to drinks with girlfriends, a date night, or a chic holiday party.
What would I wear with it? Gold metallic heels would really bring out the metallic details in the skirt of the dress, but black heels would be equally chic! A gold or black clutch would seal the deal.



#3: Red Plaid Tunic Dress:


You can never go wrong with a classic red holiday plaid, and this dress is a festive go-anywhere style for the holidays! This dress has a slightly more casual feel than the other two, but could very easily be dressed up with heels and a clutch as I’ve shown here. This silhouette is a favorite of mine – it’s got a great puff sleeve and a flouncy tiered skirt, which just feels fun to wear!
Where would I wear this dress? This is yet another versatile option for many holiday occasions and would really depend on how you accessorized it! I would easily reach for this dress to wear to a festive lunch, a holiday work event, a school function, or a dinner party with friends.
What would I wear it with? For more casual occasions, I would pair with a chic ballet flat. For dressier occasions, I would add a metallic heel and a clutch!





I hope this post gave you some holiday outfit inspiration! If you love any of these looks, you can use the code ALEXANDRA15 for 15% off site-wide at Sail to Sable!
Also, in case you missed it, I shared a reel with all three looks in action on Instagram!
Wishing you lots of fun in your holiday outfit planning!


