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!

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!

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.

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!

Did you like this post? 

Subscribe to get email updates! In addition to my most recent blog posts, you’ll receive exclusive newsletter content like special sales, my newest favorite finds, and an occasional peek behind the scenes — all delivered right to your inbox.

This post contains affiliate links. When you shop through my links, it helps support my business (at no additional cost to you) so thank you!

photos: Alison Cornell

Join the Conversation

22 thoughts on “Winter Date Night Outfit: Grey & Black with a Pop of Red

  1. I LOVED this series and liked it over the 5 days rather than in one post. Great idea and hope to see more like it. Thanks for the inspiration and good info!

  2. I was soo excited when I saw this last outfit, as I have all the pieces!  Last fall, I found a  red Kate Spade crossbody with the combo chain/leather strap for $40!  #jlsfashioncopycat. I wholeheartedly agree with you about the importance of date night, especially for the young couple whose world is filled with running for their children’s activities.  We have date breakfast, lunch & dinners now that our girls are gone!  But scheduled in between our grandchildren babysitting commitments!  Actually our favorite time is in the morning right after we get the kids on the bus, sitting/enjoying the quiet, maybe on the front porch, with coffee in hand and just talking!  Except Thursday & Friday, when the 3 year old comes for the day, #notsoquiet!  Have a wonderful weekend and wishing you success in picking out appliances & finishes for your kitchen reno!

  3. Hi. Just some feedback as I enjoy following you and your outfit suggestions for the past year+. Not everyone’s spouse is opposite gender so perhaps you could incorporate gender neutral pronouns like ‘they would appreciate it’, or something similar. My wife is an amazing dresser who knows her style, I’m still trying (at 49) to learn what works for me outside of work; so I want to feel included in your audience. Thanks for reading.

  4. I really like this outfit on you!  As our lives have evolved, including Larry dealing with the cancer and the other health challenges that it has brought on, we don’t have date nights.  That’s why when he does have doctors appointments, I try put some real effort into selecting my outfit, and I try to look nice for him.  And yes, he will let me know when I am wearing something that he really likes.  Because both of us love riding our four wheelers and being in the woods, I feel like that is a different type of date for us.  However, that is not when I put on a nice outfit! 🤣. Have a great day and weekend!  The prediction now is that we are going to have worse severe weather late tomorrow and into the night, than they originally thought. 🙏

  5. Used your link to grey cotton sweater to take the Everlane plunge and ordered a pair of jeans under Pay What You Want, taking advantage of my one-time free shipping and returns.

  6. I think it would be fun if you do not necessarily a date night essentials post, but get into the specifics of what elements you can add to an outfit to make it more of a date night than everyday.

  7. This was a nice series! I would love to see other series about once a month, it is wonderful to see ways to stretch our dollar!! I have an unrelated question, there has been chatter online about being careful buying name brand merchandise online. There are some saying that websites are selling premium brands that are not authentic!? Do you know or can you research as a topic? Buyer be aware!!

  8. The gray v-neck Everlane sweater listed below and the Hologen crewneck from today’s post are both my go-to pieces too, but especially the Everlane sweater. I probably wear one at least once a week in the winter—they both feel wonderful (not itchy!) and have a nice fit. The Everlane sweater works for cool fall and spring days too!

  9. I liked the 5 ways spread out over the week. Perhaps a 5 ways to wear blazers or cardigans post. Or, a 5 ways to wear black or gray dress pants for a work wear or church look.

  10. Cute outfit. I have a similar grey cashmere sweater and love how versatile it is as you’ve shown us in the series! I definitely try to choose quality over quantity – it’s worth it in the end. Have a fabulous weekend!

  11. I like the 3/5 way to wear a piece of clothing. It gives us fresh eyes on something in our closet. I would have liked to have seen the grey sweater worn with something other than  skinnies/slim fit bottoms. Perhaps a skirt, straight leg pants, dress pants, over a dress, etc. making us think outside of the box. I hope this doesn’t come across as criticism or at least constructive criticism. 😉

    1. That’s good feedback. Definitely could have done a look with my black bootcut trousers for work… or even my bootcut jeans.

      For this series, I threw it together last minute – I was meeting Alison to exchange gifts, and it was a pretty day, so she said we ought to shoot some outfits. I had nothing on my calendar, but I knew I wanted to do this series, so I threw together these 5 looks with what was in my closet in about 10 minutes and ran out the door. I wasn’t really thinking beyond what I typically wear, but in the future, I’ll try to plan these a bit more and add a work wear look to the mix.

      As an aside, I don’t even own a skirt, lol!!!

  12. This was a great post on the grey sweaters, and was nice spread over the week. I would like to see one quality item styled several different ways since the emphasis will be put more on purchasing quality pieces. Also what makes a piece good quality, besides price? as sometimes items are priced high but aren’t necessarily good quality? What should we look for? I am trying to build a more staple wardrobe with quality pieces not necessarily the trendy items so this would help. Also what Shoes look best with different jean trends? sometimes I’m all set to go but then the shoes I have may not work or look the best. Maybe a post on the correct and incorrect selections. Just thoughts….
    Heading out to dinner actually with my hubby shortly. Very last minute, but easier now that we have one married and the other older one still at home has their own plans. I don’t tend to go over the top for these dinners out but always pick the nicer sweater or blouse to put it up a notch. This time of year its sooo cold that the turtleneck usually wins for the dinner out. LOL
    Happy Weekend

  13. Such cute sneakers. Let us know if they are comfy. May get a pair. Glad you got to run/walk. I biked today as it was 66 here.

  14. I prefer the 5 ways series to be in one post, since it allows for more variety in the week. But, I will read either way!!

    1. Thanks for that feedback. I hear ya… it is nice during these slower times of year when I don’t have as many blog post topic ideas as days in the week. 🙂 I will also try to make the next one have a little more variety. Also, the one post ones are better for when I’m pulling from the archives and not shooting all new looks. I will likely do some of each in the future. 🙂

Want More?

Jo-Lynne Shane on Instagram

Click an image below.

Follow @jolynneshane