Best Winter Date Night Outfit Ideas For Each Type Of Date

November 17, 2022

Is it just me, or does this time of year always feel extra romantic? I love going on dates during the holiday season as we approach winter, whether it’s grabbing a cup of hot cocoa and going to see all the seasonal holiday light ceremonies or having dinner in one of those cool igloo things many restaurants started using during the pandemic. 

My husband and I have always made an effort to plan special date nights as often as possible, but since finding out I’m pregnant, we have been putting in MORE effort to spend quality time together before the babies arrive! 


Ice Skating

This is also a go-to pregnant ladies’ date night (even though we can’t go ice skating), believe it or not. Skating requires athleticism whether you want it to or not, so for this sporty date night you’ll want the flexibility that leggings give you. Wear a cute pair of leggings with tall boots and an oversized sweater, like this best seller, so that you can easily slide on and off the skates all while still having a cute fit for post-drinks or dinner! 


Casual Dinner Date 

If it’s a casual dinner date, I love jeans and an off-the-shoulder sweater. If you aren’t about off-the-shoulder, try a deep V sweater for a sexy look. Check out other date night sweater looks that I love to pair with jeans. 


Grabbing Drinks/First Date Drinks

If it is your first date, I love jeans, chunky heels, and a long sleeve date night top. Check out these date night tops that I love. If you aren’t totally sure of the vibe of the bar then wear dark jeans with a top that is pink or red to give some pop. I also swear by colors for making a difference in first impressions and putting you in a confident mood which is exactly what you want for your first date. 


Lights Ceremony

Jeans and a cute casual top whether it be a sweater or a tight-fitted long sleeve is a cute date night outfit. Make sure you sport combat boots and wear your cutest outer garments (gloves, hat, and scarves). A teddy bear jacket looks super cute for those Insta pics! 


Maternity Winter Date Night

For moms-to-be, chances are you are doing way less socializing if you are anything like me. If that is the case, chances are you are doing an early evening out, maybe dinner or a work event. I like the idea of a sweater dress that is long sleeve to keep warm with heels or a fuzzy sweater top with a midi skirt and heels. Make sure to pack a warm jacket if you live up North! 


Musical/Play AKA Dressy Winter Date Night 

I would wear OTK boots and a dress/skirt and tights. OTK boots are key to a fancy date night out. These always add a sexy touch and can always enhance a dressy outfit. If you go with a shorter dress or skirt, pair your OTK boots with tights. If you are wearing a midi sweater dress, focus on your accessories and wear an elegant long-fitted coat. 

When in doubt, always remember that you can go to the classic LBD and dress it up or down. Check out stylish size inclusive and tall girl friendly LBDs here my fav ways to sport the LBD here


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