Winter Date Night Outfit: Grey & Black with a Pop of Red

Happy Friday, friends! Cheers to the weekend! Today I’m wrapping up 5 Ways to Wear a Grey Sweater with another winter date night outfit.

Jo-Lynne Shane styling a winter date night outfit with a leather jacket, suede over the knee boots, black jeans, a grey cashmere sweater, and a red bag... Click through to see how it came together!

Someone asked in Tuesday’s post, What makes an outfit a date night look instead of just an everyday outfit?

That’s a fair question.

What The Heck is Date Night?

Believe it or not, “date night” is actually in the online dictionary. (Yes, I googled it. #wordnerd)

From Dictionary.com: “an evening social date on which a married or long-term couple go out together” or “a night of the week on which it is usual or customary for couples to go out on a date.”

And the Urban Dictionary actually adds this caveat: “Not to be confused with a Date, as that is between unmarried couples solely.” So there ya go!

Whatever you want to call it, I think it’s important to “date your spouse,” and I like to dress differently when we go out together than I do for work or church or everyday life. It makes our time together seem more special, and I think he appreciates it too.

What Makes a Date Night Outfit?

When I think of a date night outfit, I’m going for a look that’s dressier than what I’d wear to the grocery store or the mall, sexier or edgier than what I’d wear to work or church, but not as formal as a cocktail dress… unless the situation requires that!

Jo-Lynne Shane styling a winter date night outfit with a leather jacket, suede over the knee boots, black jeans, a grey cashmere sweater, and a red bag... Click through to see how it came together!

In this case, the over-the-knee boots plus the leather jacket take the outfit to “date night” territory.

Both are versatile wardrobe pieces that I mix and match with other looks and wear for a wide range of venues, but when I put them together, the outfit takes on an edgier vibe than what I would wear to run to the mall or volunteer at my kid’s school.

On the other hand, it’s not as conservative as what I would wear to church or to the office, making it perfect for date night!

Jo-Lynne Shane styling a winter date night outfit with a leather jacket, suede over the knee boots, black jeans, a grey cashmere sweater, and a red bag...see how it came together!

Incidentally, I’d consider this winter date night outfit a great GNO (girls’ night out) look as well!

I kept my jewelry fairly simple, but I did add a red bag with silver chain detail for a little pizazz. The hardware has a more rugged/edgy vibe than most of my other bags, and I like the element of interest it adds to the look.

Unfortunately, this one is from last year, and it sold out, but I’ll link up some other options.

Pop of Red

In fact, almost everything I’m wearing is old. The leather jacket and OTK boots were both purchased on a major sale, and they’re closet staples I wear over and over.

The sweater is the Halogen cashmere crewneck, and the jeans are my black AG Farrahs.

Do you have a regular date night with your spouse, or at least make it a priority?

We go out a lot, but it’s not a regular night or anything. It’s a lot easier now to find time to go out together than it was when my kids were young and needed babysitters, and we often take advantage of the nights when they’re out with friends and make it a spontaneous outing.

But if it’s been a while, sometimes we will plan something because we need that time to talk uninterrupted.

Other times, we go out with friends, which is fun too, but I do think it’s important for the two of us to go out alone every so often, because you can have conversations you can’t have with anyone else around.

At any rate, I hope this winter date night outfit inspires you to level up a bit when you go out with your significant other. I guarantee, he will appreciate it, and you’ll feel great too!

Jo-Lynne Shane styling a winter date night outfit with a leather jacket, suede over the knee boots, black jeans, a grey cashmere sweater, and a red bag...see how it came together!

Outfit Details:

grey cashmere crew // similar leather jacket (faux option) // black skinnies (budget option) // OTK boots // red crossbody bags

I hope you liked this series on 5 Ways to Wear a Grey Sweater!

You can see even more ways I’ve worn a grey sweater here.

And I’m wide open to ideas for other 5 Ways posts. Let me know if you prefer all 5 outfits in one post, or spread out over the week like this one.

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Jo-Lynne Shane shares 5 ways to wear a classic grey sweater for women over 40, with other wardrobe basics for a variety of fall/winter outfits you can recreate from your own closet!

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photos: Alison Cornell