Turning Heads Linkup – Wearing a Spring Dress with Sneakers - Elegantly Dressed and Stylish
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Turning Heads Linkup – Wearing a Spring Dress with Sneakers

I wasn’t sure about this look when it first became popular. Visions of ladies in suits with large, clunky Reebok sneakers from my teenage days when I worked in downtown Pittsburgh filled my head. Today, though, a “sleeker sneaker” ( you like that?) such as these classic converse, are worn as a casual style with a longer periwinkle dress.

Getting my things together today to head to Harleysville, PA, as we visit my in-laws for a week. We leave on Thursday. We make it a trip each Memorial Day to see family, and the bonus is I get to visit my brother in VA on the way there. We make a pit stop at his place and break up the ride as it is a long trip otherwise.

Good news! We think. We had a trial run with Truffles in the car down to my PT about an hour away, and she did quite well after we gave her the Silio med, Not “dazed and confused” just seemed more relaxed. I told her to sit down and she did and laid in the back without frantically trying to get up front. There may be hope afterall!

My Outfit

This outfit- I love the periwinkle color of this Coldwater Creek dress I received years ago on the blog, and fancied the look with my denim jacket and my new sneakers, or in Pittsburghese, “tennies”. I realize I could have chosen a more casual bag other than  my Brahmin, but the color was too perfect not to use it! A white circle straw bag, or my bucket bag would have made the look even more casual.

For a sporty look, but keeping it feminine, add a detail like a flower brooch or some floral earrings. Mine are from Baublebar from last season.

I know for a while, the clunky chunky look in sneakers was trendy, but that brings me back to my Downtown work days in Pittsburgh. It’s not for me. I like the fact that these are streamlined, and a casual slip-on style would work as well. I just love these Converse, the old-school vibe they give along with a bit of “tomboy-edge.” I am old-school in certain ways, so these fit right in! I also dig the platform, adding cushion and a bit of height.

Jean jackets are a great staple for Spring, and I grab mine often. I have 2 styles, and this one from Anthropologie was bought on Poshmark for $70!

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  • Hilda Smith
    Posted at 14:08h, 26 May Reply

    I love denim jackets with dresses and I too have a post up tomorrow with dress and denim jacket..no sneakers this time but I love dresses and sneakers too. It does depend on the dress. You look tall in yours!

    • Jess Jannenga
      Posted at 14:45h, 26 May Reply

      I wear my denim jacket alot in the Spring. I wanted a dresser lace topper that I could wear with dresses when we go to dinner or the show.. but denim jackets go with everything in the sprng. Thank you Hilda! I am 5 foot 9, so im tall, i suppose 🙂 xx

  • This Main Line Life
    Posted at 08:58h, 24 May Reply

    Love that dress. The color is so pretty. I just ordered a jean jacket from Nordstrom because I’m feeling left out of the whole jean jacket/dress trend, lol.

  • Helene Goldnadel
    Posted at 04:27h, 24 May Reply

    Incorporate the elements of the season and create a fresh, beautiful fairytale atmosphere.

  • Anna Marcus
    Posted at 19:20h, 22 May Reply

    Cool sneakers Jess. Lovely look Jess, great combo of “girly” dress and chunky trainers

  • Carrie @ Curly Crafty Mom
    Posted at 16:16h, 22 May Reply

    I love these slimmer sneaks with this periwinkle colored (such a pretty color!) dress, too! I agree, there are so many more options with sneakers these days!


  • Meagan Brandon
    Posted at 07:25h, 22 May Reply

    Sneakers with a dress is such a fun outfit – I love the combination of chic and sporty! Such a pretty Brahmin, too!


  • Linda Cassidy
    Posted at 07:06h, 22 May Reply

    sneakers and dresses my fav spring summer look. This is a great look for you

  • Cheryl Tucker
    Posted at 21:06h, 21 May Reply

    I love your choice in sneakers! I agree that you need just right sneaker for this look and you nailed it!

  • stinedurfdl
    Posted at 19:39h, 21 May Reply

    Sneakers and a dress/skirt is one of my very favorite combos! Love the shade of blue on you Jess! xo

  • Emma Peach
    Posted at 17:45h, 21 May Reply

    Gorgeous dress, it looks fab with the sneakers and denim jacket! I’d love to wear my Stan Smiths with a dress but I’ve got massive feet so I feel self conscious. I need a bit of a platform or wedge to make them look smaller.

    Emma xxx

  • aquamarinastyle
    Posted at 17:25h, 21 May Reply

    Love the periwinkle dress, Jess. Such a great spring color! I was leary of the sneaker and dress look, too, but I’m getting over it as so many of you look so cute in that style! Plus they are so comfy–can’t beat that, right?

    xx Darlene

  • Laura Bambrick
    Posted at 15:55h, 21 May Reply

    This outfit is perfection! I absolutely love that shade of blue on you! It is beautiful! Sneakers are the perfect way to dress it down!

  • fiercefashion
    Posted at 15:08h, 21 May Reply

    This is such a perfect outfit. I’m glad you chose your Brahmin even though it’s dressier. I keep looking for athletic shoes that don’t hurt my feet, I hope I find some!

  • Phyllis Lerner
    Posted at 14:58h, 21 May Reply

    I love the way you dressed down this look with the sneakers and denim jacket. So cute for spring or summertime.

  • Cheryl Shops
    Posted at 14:32h, 21 May Reply

    I love a good dressed-down dress, and you pulled it off perfectly! This reminds me that I need a new pair of Converse All-Stars too! Mine are so old that the insole has started to disintegrate 😉
    Cheryl Shops | http://www.cherylshops.net

  • eyeloveknots
    Posted at 14:04h, 21 May Reply

    I think the trend requires the right kind of sneakers, and I think you’ve aced it!


  • Gail Hanlon
    Posted at 13:54h, 21 May Reply

    I love the look of a dress with sneakers and a denim jacket. Beautifully styled as always.

  • Jacket Society
    Posted at 12:33h, 21 May Reply

    I love sneakers with dresses and your look is just fab. Love the whole outfit.

  • Sherri Preston
    Posted at 12:16h, 21 May Reply

    I love the idea of sneakers in the spring and summer with almost anything..depending on the type of sneakers. I really like you idea, and pictures of wearing them with a dress!

  • Lisa Richardson
    Posted at 11:57h, 21 May Reply

    You wear so many colors so beautifully and this is no exception. I’m so glad sneakers and dresses are a thing now. So comfy! XO

  • budgetbelles80
    Posted at 10:28h, 21 May Reply

    I like “sleeker sneakers” like Converses and Keds because they look so good with skirts and dresses. I love how you styled your look.

  • Marta
    Posted at 10:08h, 21 May Reply

    I wasn’t a big fan of the trend either but now I really like it. And I prefer the classier sneakers too, I have a big collection of Coverse look-a-likes.

  • Suzy Turner
    Posted at 10:05h, 21 May Reply

    I adore dresses with sneakers, Jess and your look is absolutely GORGEOUS!!!
    Suzy xx

  • Jennie
    Posted at 10:05h, 21 May Reply

    This is such a pretty dress! It looks great styled with the denim jacket, brooch, and All Stars. This is my kind of look for spring and summer! Hope you have a wonderful trip, Jess!

  • makeupscholar
    Posted at 10:02h, 21 May Reply

    Love this post Jess!

    It’s such a great casual look for spring and summer. I love your suggestion to make the look more feminine with a brooch or floral earrings – it really makes a huge difference! 🙂

    – Laura | https://makeupscholar.com

  • shelbeeontheedge1
    Posted at 08:58h, 21 May Reply

    Jess, while I have been way more into dresses with booties, I do love the sneakers with dresses trend so much, too. You look adorable! And I am with you about the suits and sneakers from years gone by. That just makes me cringe. This is totally different and way cooler! Have a wonderful weekend in PA!


  • Jodie
    Posted at 08:48h, 21 May Reply

    I just love this trend too Jess. It’s so functional really. You can look nice in a dress and still be able to walk around comfortably!!

  • Amy Johnson
    Posted at 08:22h, 21 May Reply

    I wish I looked so good in sneakers and a dress! I love the look on others but when I try it I look frumpy. That dress is so pretty. Love the color.

  • Lisa D.
    Posted at 08:05h, 21 May Reply

    While shopping this past weekend, I saw a lot of dresses with sneakers in the store front windows. I think its trendy and looks fun. I was telling my husband that it reminded me of the 50’s. I love this style.

  • dousedinpink
    Posted at 07:26h, 21 May Reply

    The print and color of your dress is gorgeous! Love your styling with the denim jacket and sneakers!

    Jill – Doused in Pink

  • Mica
    Posted at 07:23h, 21 May Reply

    Such a cute spring outfit! I love Converse with dresses and denim jackets 🙂

    Thank you for the link up!

    Hope your week is off to a great start 🙂 The weekday wear linkup is live on my blog, I’d love you to join! 🙂


  • mireilleftm
    Posted at 07:22h, 21 May Reply

    A pretty look! I have been wearing my converse a lot with skirts and I like them with my maxi dresses too!

  • Andrea Nine
    Posted at 07:06h, 21 May Reply

    You know I love the dresses and sneakers together so this is fabulous!! You look darling Jess!

  • thisblondesshoppingbag
    Posted at 06:52h, 21 May Reply

    Periwinkle is so pretty – love that dress and the way you styled it with your tennies! I think denim looks so good with periwinkle too and yes to the Brahmin bag!
    I’m so glad to hear that Truffles seems to be a bot calmer with the new med – I may be talking to you about that for Sophie – she freaks out when it storms and rainy season starts soon!
    I’m excited for your trip – I hope y’all have a safe drive and you feel good once you arrive!

  • Chrissy
    Posted at 06:23h, 21 May Reply

    I love this fun look. It reminds of the 50s just a tad with the white sneaks and dress. Also, you’re right, the brooch adds such a pretty feminine touch! Always pretty Jess!

  • Mary The Pouting Pensioner
    Posted at 06:08h, 21 May Reply

    Sweet outfit, Jess . I can’t bring myself to jump into the sneakers and dress thing yet but I am embracing the jean jacket and dress pairing with great enthusiasm!
    Hugs, Mary.

  • Maureen
    Posted at 06:03h, 21 May Reply

    I love Converse shoes with sundresses! It’s a casual look that I of course tend to love and lean towards. The periwinkle color of your dress is beautiful. I don’t see a lot of clothes in this shade so when I encounter one in real life or online, it’s always so fun! Brahmin bags are stunning. I like that it matchy matches your dress! I hope your week is going well so far and happy Tuesday!

    Maureen | http://www.littlemisscasual.com

  • Vanity And Me Style
    Posted at 02:15h, 21 May Reply

    I really want to try the trainers and dress look but I’m worried about my height Jess. I love how this combination takes the look from classic to bang on trend xx

    • Linda Cassidy
      Posted at 07:07h, 22 May Reply

      I am 5’3 3/4″ and I adore sneakers with a dress you will love it

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