Holiday Outfit Ideas: What To Wear for a Holiday Date Night

Welcome back to our 12 Days of Holiday Outfits series!! Today we’re going to discuss What To Wear for a Holiday Date Night. 

12 Days of Holiday Outfits: What To Wear to EVERY event this holiday season

Okay, we may be reaching with this one, but you try coming up with 12 themes for holiday events and see where you end up.

And seriously, if you do NOT have a holiday date night planned with your significant other, I challenge you to make one right now. This is such a busy time of year, but that’s not an excuse to neglect our most important relationships. This post has actually challenged me to take my own advice and plan a date night with my husband. We love to go out to eat, so we’re going to find a babysitter and make reservations for next week, after the Thanksgiving festivities have died down. We will plan our holiday gift lists and just spend time chatting and reconnecting. I cannot wait.

Rack Room Shoes is one of our sponsors for our 12 Days of Outfits  series, and they provided me with a gift card to do some shoe shopping — in addition to the $250 Rack Room Shoes gift card someone is going to WIN! (Don’t forget to enter!!) So on Saturday, I went searching for a couple pairs of chic dress shoes to style for these date night outfits.

Date Night is the time to take a few risks. You know your own comfort level, but definitely use this opportunity to play up your best asset or your favorite feature. (Or his favorite feature???)

This is one of my favorite date night outfits from last winter.

Date Night Outfit Ideas for Women Over 40

I bought the top and jacket at White House Black Market to wear to my husband’s birthday dinner. I love the top, but it is rather bare, and we are talking about the holidays when temperatures tend to be quite cold for most of us so the jacket was an obvious necessity. It also adds interest. I purposefully chose a jacket that has some feminine details. I didn’t want it to look too corporate.

These pieces are no longer available, but it’s a great example of a stylish date night outfit for the over-40 set. At least, I felt pretty hot for an old lady. Ha! I recreated the outfit yesterday with dark wash skinny jeans and these black patent pumps from Rack Room.

Chic Date Night Outfit

Chic Date Night Outfit for the Holidays or Any Time!

Here is an example of an outfit with similar items that are currently for sale.

Holiday Date Night Outfit featuring White House Black Market & Rack Room Shoes

Shop this look: Black Leather Peplum Jacket (sold out; alternative ponte black jacket) // Red Halter // Black Velvet Skinny Jeans // Madden Girl Black Pumps via Rack Room Shoes // Silver Minaudier at Kohl’s

Here’s a similar but more conservative look. If the above look isn’t really your style, you might like this one. For this look, I styled these chic booties, also from Rack Room Shoes. The scarf, gray top and coated cotton moto jacket (NOW 50% OFF!!!) are all from LOFT. The earrings are from my Stella & Dot boutique (you can now earn Dot Dollars!!) The red bag and black ponte knit pants are as old as the hills (one of my mother’s favorite expressions . . . )

Classy Winter Women's Work Outfit

As far as the jackets are concerned, they don’t have to be black, of course. I love this look — winter white jacket over a sequin tank with jeans.

white jacket for date night

Aren’t the booties so cute?

Date Night Outfits with Chic Booties

They also look great with tights and a dress. This is another avenue you can take for a date night outfit. A cute dress. I wore this last year when we went out to dinner for Valentine’s Day. Again, this dress is no longer available, but you can find similar styles at various price points.

Date Night Outfit: Bold Patterned Dress with Tights and Booties

The booties definitely take it up a notch and keep it current, but pumps or tall boots would work just as well. It all depends on the level of formality you’re going for and your personal comfort, of course!

You probably have something in your closet, but if you need some shopping suggestions, I found a few dresses for you to peruse.

Even if you’re staying in or meeting your honey for a coffee at Starbucks, I encourage you to take a few extra minutes to throw on something that makes you feel pretty. I think our men appreciate it, and even if they don’t really care (because of course they love us just the way we are) I think we tend to enjoy our time together more when we feel good about how we look.

Want more fashion inspiration? Be sure you’re following my Fall & Winter Fashion board on Pinterest.

Follow Jo-Lynne Shane’s board Fall & Winter Fashion for Moms on Pinterest.

In case you missed it, I’m partnering with Kristin from BonBon Rose Girls and Cindy Spivey from Walking in Grace and Beauty to bring you 12 days of posts about what to wear for EVERY event this holiday season so be sure to visit both of them to see what outfits they put together for a home holiday party look!

12 Days of Holiday Outfits

See the rest of our 12 Days of Holiday Outfits, and don’t forget to enter to win a $250 Gift Card to Rack Room Shoes!

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5 thoughts on “Holiday Outfit Ideas: What To Wear for a Holiday Date Night

  1. Awesome! I love this post!

    Question for you…what do you do with clothes or shoes that aren’t on trend anymore?

  2. The booties are fab with the dress, yr right – they can really update an outfit. I’ve been inspired to buy some new skirts & dresses and will be wearing them with different types of shoes/boots and we now have a babysitter so can socialise again:-)

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