Summer Date Night Look

Now that our kids are older and can be by themselves for a few hours, Paul and I often go out to dinner as a way to get out of the house… and to save me from having to cook! We both love good food and drinks, and we have fun trying new restaurants and visiting old favorites.

Working from home most of the time, I don’t have a reason to get gussied up very often so I like to use these “date nights” as an opportunity dress up a bit. I’ve had people ask me, in a rather condescending tone at times, “Do you really dress differently to go out to eat with your husband than the rest of the time?”

Um, yes. Yes, I do.

Summer Date Night Look: off-the-shoulder top with white jeans and wedge sandals

I mean, the poor guy has seen me in the worst of times and he’s still hanging in here 22 years later. I figure the least I can do if he’s taking me out to dinner is clean up a little bit.

And yeah, I do it for me too. I enjoy dressing up! But I also feel like it’s a way to show him he’s important enough to get dressed up for. I don’t go all out — I usually just wear jeans, but I like to swap out my typical t-shirt for a fun top and my flats for heels.

Summer Date Night Look: off-the-shoulder top with white jeans and wedge sandals

This floral off-the-shoulder top is a perfect example of what I look for in a “date night” top — it’s flirty and fun and a step above the tops I typically wear to run errands around town.

I don’t mind off-the-shoulder tops for a few hours, but I don’t really care to wear them all day. This one is nice in that you can also wear it on your shoulders. Not all of them work well both ways, but this one does. It’s also on sale, and at the moment, available in all sizes!

Summer Date Night Look: off-the-shoulder top with white jeans and wedge sandals

If you’re in need of a strapless bra, I highly recommend this one. Cyndi turned me on to it last summer, and it was a total game changer. It’s actually, dare I say it… quite comfortable. A least as far as strapless bras go. It also has the convertible straps, should you need those.

For this look, I paired the floral top with my go-to white jeans and a pair of espadrille wedge sandals. I like how the black in the sandals bookends the outfit since black is the base color in the top.

Summer Date Night Look: off-the-shoulder top with white jeans and wedge sandals

I kept it simple and carried a black clutch. I don’t always match my bag to my shoes, but sometimes I like to and it seemed to work out well in this case.

This Gigi New York clutch was gifted to me a few years ago, and it’s a great gift idea if you ever want something unique for a special someone in your life. I love how you can have it monogrammed.

Summer Date Night Look: off-the-shoulder top with white jeans and wedge sandals

I’ve had these earrings for a while, but I tend to wear them more in the summertime for some reason. They just look light and summery to me. I love how the white agate in the gold frame shows up against my dark hair and draws out the lighter colors from my top.

After I shot this look with Alison, it was around lunchtime, so I texted Paul and told him that he should take me out to lunch since I was all glammed up. It didn’t work out, but at least I’m all set for our next date night!

Summer Date Night Look: off-the-shoulder top with white jeans and wedge sandals

blouse // jeans (option) // shoes // clutch c/o // earrings // bracelet

photo credit: Alison Cornell

Be sure to visit Cyndi and see the summer outfit she’s styling today!

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50 Responses

  1. This is a fabulous summer date night look. I always get dressed up for date nights too and for the exact same reasons you mentioned. Nothing wrong with wanting to make an effort!

    Unrelated but I’ve been meaning to ask..Are you not using Like to know it anymore? I’ve noticed I haven’t gotten any of your IG photos in the app all month.

    1. No, I’ve been experimenting with ShopStyle this month. There’s a link in my IG bio that links to all my IG outfits here on the blog. I wondered how many of you all were using the app – I never really promoted it so I wasn’t sure if many were using it or not.

  2. Jo-Lynne, you look fabulous in this outfit!  I am trying to dress better when we go out to dinner, even when it’s just to the best restaurant we have in town.  It makes me feel better about myself, and I appreciate when Larry notices & comments on it.  Have a blessed day!

  3. Love the look for head to toe. I also really like your makeup looks so natural, I know you have posted your make up likes before, the colors are what I like color of foundation eye shadow blush and lip color. the reason I ask is I am switching up my colors for summer and want that natural look.

  4. Such a pretty top:) I’m in the same boat since I work from home. I too prefer a more casual and comfy look throughout the day. I’m not like these tv commercials where I’m vacuuming in my heels. LOL, So when my husband and I get a chance to head out I like to step it up a notch, or if we are meeting up with family and friends as well. Very pretty look on you. Thanks for sharing


  5. I love this outfit! I also enjoy dressing up for date nights. My kids are almost exactly the same age as yours so we can also enjoy some evenings away. I recently found a new strapless bra that I LOVE. I bought the one you have linked last summer and it is a great bra but I actually like my new one better. It’s Victoria Secrets new technology called illusion strapless. It’s lightweight and not binding at all. I rarely shop at VS but had a gift card and was pleasantly surprised by this bra. Just wondering if you’ve tried it and what your thoughts are.

  6. You look adorable in this outfit.  Thanks for posting about the strapless bra also, going to order one.

  7. I love this top and your shoes.  And good for you for dressing up a bit when going out with your husband!  I do, too.  We all made an effort when we were dating them, why not continue to?  I mean, we still want them to think we look good, right? (Hopefully)

  8. Oh my gosh! This top is so pretty! I am loving this series. I also appreciate your honesty and practicality when you are breaking down the elements of an outfit. Today you mentioned that you like an off the shoulder shirt for a few hours,not all the time and then buying this blouse made so much more sense… it’s not necessarily intended to be worn all day doing housework or running errands… it’s an item that I can invest in to take things up another notch without being overdressed. You give the best fashion advice!!!

  9. This is one of my favorite blogs. You look classy casual. Your top, shoes, earrings, clutch, even the Wacoal bra recommendation – fabulous! I have no shoulders, and one shoulder slants down a lot more than the other. I spent years trying new bras, wearing silicon bra strap holders, tape, you name it, to keep my straps up. Then I was introduced to a Wacoal bra and my straps falling ended. I will try the Wacoal strapless bra to see if it stays up underneath my summer tanks. The clutch – expensive, but timeless. Thank you!

  10. Such a pretty top and look on you!  And, p.s., this is SUCH a peeve of mine; getting the “why are you so dressed up?” comments.  Grrr.

    What’s wrong with looking nice?  Seriously, you’re wearing a top and jeans and sandals.  Hardly FMPs, body-con dress, and cleavage.  Sheesh.

    I, too, like to dress nice for my husband of seven years and, frankly, appreciate that he dresses up for ME when we get babysitting to go out.  He showers and shaves and puts on nice jeans and a nice Polo shirt, etc.  Nothing fancy, but I hate how slovenly we are as a country.  Not every moment of every day we need to be schlubs.

    Enough soapboxing, but this makes me crazy!  

    Enjoy your chances to get out kid-free, and I know you are happy you still enjoy your husband’s company after 22 years and he, yours.  THAT is an awesome achievement.

    1. I rarely comment although I read this blog all this time, but Heather, your comments are spot on! I love dressing up for date night, or heck, even just to go to the movies with the husband and kids. I’m proud that I look nice, partly thanks to Jo-Lynne, and don’t understand why some people wear the same clothes they were gardening in out to dinner. I think i get it from my mom, who always “dressed” to go to “town”. Now I have a reputation among family and friends for looking nice (and wearing great shoes!) and I’m proud of it! 🙂

  11. Date nights and date night outfits are the best! I love to spruce up and go out with my hubby of 27 years. I’m so thankful for Mike and our beautiful children and the life the Lord has blessed us with. Taking care of myself and dressing nice for him is seriously the least I can do to honor him and he does the same for me. A great marriage isn’t 50/50 it’s 100/100. Thanks for sharing!

  12. Wow!   You are truly a beauty that the camera loves!!   You have got to be a photographers dream!  Anyone can stand in front of a camera, but you have to have that model posing ability, and you’ve got it!  Now for the outfit.  Eye catching for sure!  What an elegant top to dress up white jeans!  I’m with you 100% on dressing up for date night & any other chance I get.  Although we are 20+ years apart in age, I’m sort of in the same boat as you, I’m a stay at home babysitting Grammy, so I have to dress for that.  But when I go out, I enjoy “cleaning” up!  A pretty top & some earrings can make all the different in dressing up a simple pair of jeans. I love that most of your outfits work for a lot of age groups.  Thanks for all your inspiration! 

  13. What a great date night outfit! Plus I love how you explain why you wear certain accessories….I have learned so much from you…..thank you! I agree with lots of the comments here, it is fun to dress up for my husband.

  14. Love the date night look! I agree it’s nice to get dressed up once in awhile to go out with your spouse. Makes it special. I have a question. Do you think wearing a crop top (button down gingham shirt tied into crop top) is inappropriate for an almost 50-year-old? With high waisted 4-inch shorts, not showing cleavage or even upper arms. I want to wear this to a rock concert or a backyard bbq. 5 ft 7, 114 lbs. don’t want to look like mutton dressed as lamb.

    1. I think it depends on your personal comfort level / where you live / the culture of your friend group…. Does that make sense? If it shows any skin in the midsection, I couldn’t pull it off, but if the shorts are high enough to provide coverage, it sounds like a fun outfit for those occasions. And I really do think it partly depends on how people in your area dress. If you’re in the south, it’s probably more appropriate than it would be up here. Does that help at all?

  15. Wowza!! You look absolutely stunning, JoLynne. I do believe this is one of my favorite looks. You always look beautiful, but this outfit is just gorgeous on you. I think it’s the perfect date night look! 

  16. I love this outfit! Almost ordered that cute top you have on, but I’m resisting (for now). However, I DID need a strapless bra, so I just ordered the one you recommended. It looks great.

  17. Love this outfit! Just what I would wear, love the top! I do have an issue with off the shoulders, they never seem to stay that way. Glad to see you can wear this one either way.

  18. Jo-Lynne, your outfit is adorable on you. I have to say that I read your blog all the time, and this “flowy” style looks SOOO much better on you than the t-shirt type tops I see you normally wear or the more fitted type tops or dresses. This outfit looks great on you. 

  19. Jo-Lynne a big thank you for all the effort you put into these fashion days, from the outfits, the pictures, the detail, and of course your many reply’s especially during such a busy season in your life right now. My favourites would be #5, #9, #12,#15,. Although you can’t go wrong with any.
    Happy painting day.. how exciting to see things start to transform. Yeah!!!

  20. PS…I also really like the SEA sweater with the denim shorts, and the stripe maxi dress, and the coffee t shirt outfit.. they may have been more Instagram, but I like them as well.

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