Updated December 5, 2023

There is something magical about winter date nights, I love the cold weather and there are so many fun things to do, from ice skating to a dinner date. I love planning winter date outfits it allows me to wear a leather jacket or a chic long coat and of course knee-high boots. The cool winter months are my favorite time of year. Choosing something special for date night is a great way to showcase winter fashion. So today, let’s plan the perfect winter date night outfit.

Thoughts on Casual Date Night Looks:

Choosing an outfit for a casual date is easy and fun, I love keeping it simple with a cozy turtleneck sweater, a mini skirt with thigh-high boots, and matching tights. If you aren’t comfortable with a mini dress, you can switch out the skirt with jeans, add a duster and a crossbody bag and you have a great casual outfit.

Thoughts on Romantic Dates

Romantic dates allow us to wear a long-sleeve knit dress, sweater dresses are perfect. They keep you warm, and depending on the styling, you can show a little skin. Again, pair the dress with over-the-knee boots, and you have a fabulous look. He’s sure to invite you on the next date.

Here I’ve styled a beautiful WOOL BLEND DOUBLE BREASTED BLAZER with button front BAILEY JEANS, a SCOOP NECK TOP, and LEATHER STRAPPY SANDALS now granted, you might not wear the strappy sandals right now, maybe a cute bootie.

What should a woman over 50 wear on a winter date? 

For starters, take into consideration what you have been invited to do and use your weather app to check out the weather for the day.  Nothing is worse than not wearing the right clothing for the weather. 

You can also check out photos on Yelp to see how formal or casual your date is going to be if you aren’t sure.  (People write reviews and take pictures of all sorts of venues now, not just restaurants).  Once you have that sorted, you can start to think about what to wear.

Winter Outfit Inspiration:

For a casual winter date night, a pair of jeans and a statement sweater could be good, wide-leg pants and a chunky sweater, or perhaps a midi skirt, boots, and a Moto jacket for a fun date night look. For a formal date, leather or faux leather trousers, a silk top and blazer or a knee-length dress of silk, or cashmere with a beautiful shoe would be great options.

This is one of my all-time favorite looks, a WOOL BLEND LONGLINE COAT LEATHER KNEE HIGH BOOTS, a WOOL AND CASHMERE BLEND SWEATER, a WOOL CHECKED SCARF. and the FELT FEDORA I am never without in the cooler months.

Winter is a great time to enjoy a cute puffer jacket, a cashmere sweater, lush cashmere scarves, and chunky boots. Well, all of all types of boots are great.  Whether it’s your first date or if you’ve been together a long time, wearing something that makes you feel comfortable and confident is most important. 

Some cute items to have on hand are a comfy-cozy sweater dress, a black sweater that can be worn with jeans or black trousers to make an all-black outfit, a black leather skirt, which would look great with a pair of chunky boots, and a black sweater. Faux leather pants can also be styled in many ways.

This is top of my list for our evening at the Pops, a gorgeous Velvet Midi Dress. Matching Velvet Point Toe Heels and an Evening Bag in Plum

For a classy look, whether casual or formal, choose one feature to highlight, and leave the rest to the imagination. For example, if you wear a lower neckline, wear a longer skirt or trousers. If it’s a first date, avoid going too sexy if you are hoping a relationship will develop.

Winter Date Ideas:

1. Walking in the snow with a cup of hot chocolate or peppermint coffee; 

2.   Checking out holiday lights; or the night sky

3.   Going skiing, or snowshoeing; or

4. If outdoor movies are showing in your area, those are fun too.

Places I love to shop for winter date night outfits:

1. Reiss
2. Holland and Cooper
3. Sezane

Here are a few additional posts you might like:

1. Mid-Winter Beauty Favorites
2. How to Dress like French Women When You Are Over 50
3. This Season’s Best Sweaters for Women over 50