What to Wear On a Winter Date Night Over 50

What should I wear for a winter date night in 2020?  

Roger invited me out on our second date this year and I am super excited.  Mind you, we’ve been together for years and we usually go out pretty regularly.  Our last date was Valentines day 2020.  Little did we know that everything we had planned for the year would be cancelled…until now.  The Florida Orchestra has worked out special accommodations so orchestra enthusiasts can enjoy an hour of live music during the holiday season.  We will be sitting alone in box seats and may look for an outdoor restaurant to get a bite to eat before hand.

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.

Needless to say, I’m excited and nervous at the same time.  Plus, it’s supposed to be cold that evening, a rarity here in Florida, so I’m excitedly working on what to wear for a winter date.

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 causal 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.

For a casual winter date night, a pair of jeans and a statement sweater could be good, or perhaps a maxi dress, boots and a Moto jacket.  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 beautiful jackets, cozy sweaters, lush cashmere scarves and boots of all types.  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. 

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.

Great winter 2020 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 snow shoeing; or

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

5. Several of the nice restaurants here are putting air filter systems in to help their guests stay healthy, and have been working out how to offer outdoor seating even in the winter, or you can figure out a nice place to enjoy sharing your favorite take out. 

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