41 In Fashion/ Link Up

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 thanΒ  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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  • Reply
    Hilda Smith
    May 26, 2019 at 2:08 pm

    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!

    • Reply
      Jess Jannenga
      May 26, 2019 at 2:45 pm

      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 πŸ™‚ xx

  • Reply
    This Main Line Life
    May 24, 2019 at 8:58 am

    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.

  • Reply
    Helene Goldnadel
    May 24, 2019 at 4:27 am

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

  • Reply
    Anna Marcus
    May 22, 2019 at 7:20 pm

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

  • Reply
    Carrie @ Curly Crafty Mom
    May 22, 2019 at 4:16 pm

    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!


  • Reply
    Meagan Brandon
    May 22, 2019 at 7:25 am

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


  • Reply
    Linda Cassidy
    May 22, 2019 at 7:06 am

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

  • Reply
    Cheryl Tucker
    May 21, 2019 at 9:06 pm

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

  • Reply
    May 21, 2019 at 7:39 pm

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

  • Reply
    Emma Peach
    May 21, 2019 at 5:45 pm

    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

  • Reply
    May 21, 2019 at 5:25 pm

    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

  • Reply
    Laura Bambrick
    May 21, 2019 at 3:55 pm

    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!

  • Reply
    May 21, 2019 at 3:08 pm

    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!

  • Reply
    Phyllis Lerner
    May 21, 2019 at 2:58 pm

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

  • Reply
    Cheryl Shops
    May 21, 2019 at 2:32 pm

    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 πŸ˜‰
    Cheryl Shops | http://www.cherylshops.net

  • Reply
    May 21, 2019 at 2:04 pm

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


  • Reply
    Gail Hanlon
    May 21, 2019 at 1:54 pm

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

  • Reply
    Jacket Society
    May 21, 2019 at 12:33 pm

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

  • Reply
    Sherri Preston
    May 21, 2019 at 12:16 pm

    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!

  • Reply
    Lisa Richardson
    May 21, 2019 at 11:57 am

    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

  • Reply
    May 21, 2019 at 10:28 am

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

  • Reply
    May 21, 2019 at 10:08 am

    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.

  • Reply
    Suzy Turner
    May 21, 2019 at 10:05 am

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

  • Reply
    May 21, 2019 at 10:05 am

    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!

  • Reply
    May 21, 2019 at 10:02 am

    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! πŸ™‚

    – Laura | https://makeupscholar.com

  • Reply
    May 21, 2019 at 8:58 am

    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!


  • Reply
    May 21, 2019 at 8:48 am

    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!!

  • Reply
    Amy Johnson
    May 21, 2019 at 8:22 am

    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.

  • Reply
    Lisa D.
    May 21, 2019 at 8:05 am

    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.

  • Reply
    May 21, 2019 at 7:26 am

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

    Jill – Doused in Pink

  • Reply
    May 21, 2019 at 7:23 am

    Such a cute spring outfit! I love Converse with dresses and denim jackets πŸ™‚

    Thank you for the link up!

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


  • Reply
    May 21, 2019 at 7:22 am

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

  • Reply
    Andrea Nine
    May 21, 2019 at 7:06 am

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

  • Reply
    May 21, 2019 at 6:52 am

    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!

  • Reply
    May 21, 2019 at 6:23 am

    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!

  • Reply
    Mary The Pouting Pensioner
    May 21, 2019 at 6:08 am

    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.

  • Reply
    May 21, 2019 at 6:03 am

    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

  • Reply
    Vanity And Me Style
    May 21, 2019 at 2:15 am

    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

    • Reply
      Linda Cassidy
      May 22, 2019 at 7:07 am

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

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