Casual Black Dress with Converse or Wedge Sandals

Hello, friends! TGIF! Today is Day 13 of my 22 Days of Summer Fashion style collab with Cyndi Spivey, and it’s also Fashion Friday so stay tuned for a fashionable linkup at the end of this post!

I styled this casual black dress with Converse Shoreline sneakers and also with a bright orange wedge sandal.

I picked up this casual black t-shirt shift dress at Target a few weeks ago. I wanted to show you how versatile it is by styling it two ways. First I styled this casual black dress with Converse Shoreline sneakers and then with a bright orange wedge sandal.

Casual Black Dress with Converse Shoreline Sneakers | Fashion Over 40

Here it is with the Converse Shoreline sneakers and my striped tote. I love this twist on the athleisure trend. We found the coolest mural to take pictures in front of. I mean, how can a fashion blogger resist this opportunity!?!

Casual Black Dress with Converse

Here’s a back view — not my favorite angle, but I’m all for full disclosure. Ideally, this dress is probably better suited for someone with a straighter body silhouette. It’s not the most flattering to my rear view, but I still like the length, the side slits, the modest V-neck, and the wide shoulder straps.

How cute is this Casual Black Dress with Converse Sneakers and Black and White Striped Tote!?!

I do wish the dress were a little more fitted, but it is a shift dress, not a sheath, and I think the looser fit makes it more casual.

Casual LBD with Striped Tote

The dual side slits make it easy to walk in and sit in, and I also think they add a fun element of interest. I wore this slip underneath so the dress would skim over my lumps and bumps curves.

Casual LBD with Striped Tote

Here’s one final look at the outfit with the sneakers.

Casual Black Dress with Converse Shoreline Sneakers | Fashion Over 40

I also wanted to show you how this dress can be dressed up with a bold wedge sandal. These Nine West Lucini Wedge Sandals are on sale for $59, and they are quite comfortable. They also come in white, nude, and black. The nude version reminds me of my Tory Burch Lexington wedges, and they’ve recently been restocked in almost all sizes.

Casual Black Dress with Orange Wedge Sandals and Black Striped Tote

I tried putting my light blue Kate Spade crossbody with this version of the outfit, but with the blue and orange, I felt like I was dressing to support a ball team (LOL!) so I switched to my small grey R Minkoff Mini M.A.C. Crossbody.

Fashion for Women Over 40: Casual Black Dress Outfit with Orange Wedge Sandals

Call me a Plain Jane, but I felt more confident in this version of the outfit.

Fashion for Women Over 40: Casual Black Dress Outfit with Orange Wedge Sandals

The denim jacket is the perfect layer for an cooler indoor venue, plus it also adds interest to the outfit.

Fashion for Women Over 40: Casual Black Dress Outfit with Orange Wedge Sandals and Denim Jacket

The orange wedges are comfortable and easy to walk in, and they go with so many outfits in my closet. I know I’ve been on the neutral shoe bandwagon this summer, but I realized that I miss having color in my shoe collection.

Fashion for Women Over 40: Casual Black Dress Outfit with Orange Wedge Sandals and Denim Jacket

When I wear a brightly colored shoe, I like to pick up the color somewhere else in my outfit, usually in my jewelry, so I chose these mini chandelier earrings with the coral stones. They are “vintage Stella & Dot” so no longer available, unfortunately.

I love how versatile this dress is and how easy it is to dress it up or down with different shoes and accessories.

Fashion for Women Over 40: Casual Black Dress Outfit with Orange Wedge Sandals and Denim Jacket

Merona Sleeveless T-Shirt Shift Dress ($19!!!) // similar denim jacket // Nine West Lucini Wedge Sandals ($59!!!) // R Minkoff Mini M.A.C. Crossbody // Chuck Taylor Shoreline Sneakers // similar striped tote // earrings (sold out) // Gorjana 3-Disc Necklace // Stella & Dot Quinn Cuff // Tory Burch Fitbit Hinged Bracelet

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44 Responses

  1. Jo-Lynne, I love this! Especially with the sneakers, as this is my reality at the moment (mum life). But I love the sandals too and how you picked up the colour in your earrings-that’s just the certain something that makes it put together. Bravo bravo bravo!!! Now I need to find the dress.
    Pas-Your rear view is nothing to fear-you look fantastic. Don’t be so hard on yourself ????

    1. LOL, thank you! You know how it is, though. You think you look one way, and you see a picture, and you’re like, Whoa!!! Haha. At least, that’s what happens to me. I forget I’m not 25 anymore. But it’s all good. 🙂 Thanks for the encouragement.

  2. I probably like the sneakers best. I can’t believe I said that, I am usually a high heel kind of gal. Life has been so hectic the past week or so, that I have missed out on a lot of your post. I hope to do some catching up later today. Thanks for the link-up. You need to join me on my new adventure of Wednesday’s Wardrobe.

    Tania @ https://www.50isnotold.com

  3. It’s really a great all purpose dress, Jo-Lynne! I think sometimes after we’re used to more fitted clothing, the non-fitted pieces feel strange. But in all reality, I think it’s nice to have variety—I’m learning that not everything needs to be form flattering!
    ps…my husband would’ve loved the Met’s colors!!

  4. I just stumbled upon your blog a few days ago and I LOVE your style! This black dress both ways is adorable and I agree with Emma. The rear view of you in this dress looks great. I wouldn’t change a thing. 😉

  5. This dress is so versatile and looks great styled both ways! I love wearing my Converse with dresses – it is definitely a go-to summer look for me.

  6. I love all the ways that you styled this! You look great. Good for you for taking a break from media when you felt you needed to. I don’t believe that you will regret it! News can get to me too much at times as well and I don’t have the Facebook app on my phone and I don’t miss it being there. Enjoy your family vacation!!

    1. Thanks, Lori. It was definitely the right decision for me at this time. I do miss it a little bit, and then I remember what it feels like to get sucked in and I am glad I’m free of that for the time being. 🙂 I tend to over think everything, and it really can get to me after a while. We’ve had a great time!

  7. That background with the map wall is amazing! That dress is so flattering and versatile, and I love the zipper on your jean jacket, how unique. Thanks for hosting!

  8. i really like how you styled this black dress. I must say though with your amazing legs, would you like it a little shorter to showcase those legs of yours?

  9. Great post! I love seeing the same clothes two or more ways. This dress is made for casual–wide shoulder, modest neckline and the length–great for busy moms who are always on the move. I love not having to worry about whether or not I’m covered in the right places as I move around!

    Having said that, I feel like it could be a little shorter and still be just as great. I especially feel like a couple inches shorter with flat sandals or converse would be better.

    The mural wall and the stone wall are amazing! I really like the stone wall!!

    And, I’m so glad you have taken a break from media while on vacation! That is so encouraging! First, your family comes first so I’m glad you’re keeping them in that position and not allowing anything to spoil that. Second, we can only take so much of all the negative—and it takes a toll on us and effects our daily life. I don’t think it’s good to be naive or unaware but we have to guard our hearts and minds (our children’s too).

    Enjoy your trip!

    1. Yes, and that is exactly what was happening. I was spending so much time considering all the points of view and analyzing everything in my mind that I was getting short tempered with the kids and I realized I needed to walk away. I think I probably need to stay away until the election is over in November, ha! 🙂

      I think the dress could be an inch shorter but no more or the slits would be too high. I actually kind of like this length – especially with the heels. I did wash it and it didn’t shrink much, just as an FYI. 🙂

  10. Love the dress on you – and definitely think it is fabulous both ways…. The casual look with the converse is adorable – you have inspired me. I have a pair just like them 🙂

  11. Hello, Jo-Lynne!

    I love how you styled this dress both ways. The first look makes it a great travel outfit to go sightseeing and exploring during the daytime. The second look just by changing the shoes and the bag makes it the perfect outfit to go out to dinner. Great job!

  12. Cute dress, JoLynne! I already try not to look at Facebook on my phone…it is such a distraction and a time drain! I may just follow your lead and delete the app from my phone. That way, I only look at Facebook on the computer.

  13. You look great! I have 2 questions…

    1) how tall are you? i’m wondering if this would be too long for me based on how it looks on you.
    2) what size are you wearing? I seem to wear the same size as you.

    Thanks and have a great weekend!

  14. I love versatile outfits! I know you’re not big on scarves, but, ohmygoodness, the possibilities would be limitless with that basic black dress as a jumping off point. Enjoy your vacation!

  15. Hello there,
    I love that map background! Would love to know where that is? Also I have to say although I am a high heel kinda gal I love the dress with the converse, the jean jacket, and the canvas bag. Seems like it would be the perfect tourist-y outfit or for running errands!

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