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Sneakers With 6 Cute Summer Outfits — That Aren’t Shorts!

Aug 2, 2019

Now that we’re in the true thick of summer and all of it’s hectic glory (?), I find myself reaching for sneakers more and more. I love how effortless and casual summer fashion is, and when it comes to traveling, sightseeing and spending as much time as possible outside this season, sneakers just can’t be beat. More comfortable than a wedge, more supportive than a sandal and at times, edgier than a flat (when paired with the right thing!), I’m loving all of the possibilities when it comes to styling outfits with sneakers.

I think we’ve allllll experienced summer fashion fails — a pair of pumps that no longer fit after your feet swell in the heat, or blisters from strappy sandals that can’t last hours in sweat and humidity. (Why are all of my examples feet-related? ?)

But really, there’s nothing worse than unhappy feet and we do NOT have time for that! The right shoes really are a game changer when it comes to enjoying ALL the summer activities — especially when you’re traveling!

I’m so glad sneakers are on-trend and that there are endless cute options and styles right now. I’m especially partial to white sneakers (especially these Tretorns and these leather Converse–as you all know from the many, many times I feature them on the blog!) and I have multiple tried and true pairs! You know you’ve found a good pair when you pack them for every single summer trip! (Pro tip don’t forget the right socks! If you missed it, check out my post on the no-slip ankle socks I swear by!) 

While I have nothing against shorts and sneakers, this post is dedicated to finding other creative ideas to wear sneakers in the summer. (Plus, many of you have specifically told me “I hate shorts! I need more summer outfit ideas!”) So below, I’ve rounded up 6 outfit ideas (without shorts!) and ways I love wearing sneakers to help get you through the rest of the season in (comfortable)? style: 

First, which sneakers to choose? 

[one-half-first]Converse on-sale at Nordstrom[/one-half-first][one-half]

Jess gives a birds eye view of her sneakers


First up–which sneakers to choose? If you want something you can wear with pretty much ANY dress, jumpsuit, pair of shorts, jeans, etc, year round,  I recommend going with something super classic and preppy.

The canvas Tretorns are my #1 pick for cute comfort (they feel like walking on pillows). They’re canvas, so yes, they do get dirty, but nothing a little oxyclean soak can’t fix. They run TTS.

However, I know a lot of you guys won’t come within 10 feet of a canvas shoe, and if that’s the case, I LOVE this pair of leather converse that I got from the Nordstrom sale. They are so cute, minimalistic, and comfortable right from the get-go! Best part? They wipe clean! They’re almost sold out right now but I’m very confident they’ll restock after the sale. (I can’t find them on any other website!) 

If you’re looking for an athletic-type sneaker, I LOVE Allbirds! They’re great for walking/travel and feel like sweatpants for your feet, haha! However, Allbirds are way harder to style with cute dresses (unless they’re very casual t-shirt dresses, example below) so if versatility is what you’re going for, go with the above pairs! 

Now…let’s get into all the ways you can style your sneakers! 

Cute Summer Outfits With Sneakers


A jumper and white sneaks complete this summer look

See full post here: The linen jumpsuit you need for every trip this summer

Jumpsuit: Treasure & Bond–wearing XS! Also comes in plus size! It runs loose/oversized. I’m also obsessed with this Amazon jumpsuit (runs TTS, wearing Small) and Everlane’s JumpsuitsJean Jacket: J.Crew Sneakers: Tretorn (Run TTS!) Lipstick: Alima Pure velvet lipstick in ‘Iris’ 

There is no better occasion for an outfit with sneakers than a travel day! Whether you’re road tripping, taking the train or hopping on a plane (does anyone else get grossed out when you’re wearing sandals through TSA and you have to walk barefoot for a few feet?!?), sneakers are always the way to go. Go full athleisure with yoga pants and a long sleeve top or dress down classic staples for an effortless travel look. 

A summer on the road and on her feet

Striped tee: (old. Love this Everlane version & this Shopbop option is on sale!) Yoga pants: Zella (on sale this weekend for $38!!) (ON SALE!) Sneakers: Allbirds Tote: Lo & Sons Suitcase: this oneDelsey–but this particular suitcase is TERRIBLE, which is so unlike Delsey because they make such good suitcases usually. It dents so much it’s laughable. ?We call him “Denty”–but I HIGHLY recommend, which is the same as my carry-on suitcase I’m obsessed with, just in a larger size! 


No your average summer outfit, Jess dresses to impress for the farmers market

Dress: Everlane (from last year, but sold out now–but here’s this year’s similar version in different colors!) Tote: tote Sneakers: Allbirds HatVineyard Vines hat (but Everlane makes plain baseball hats that are super cute too if you don’t want a logo!) 

I love taking a feminine piece, like a t-shirt dress, and making it sporty with sneakers and a baseball hat. It’s perfect for weekends at home — strolling through the farmers market, to coffee dates and running errands. I also love them with this jersey-knit midi dress. I can walk all over the city in this look and still feel dressed up enough for a patio happy hour! 

Jess is on the move, supported by great footwear

See full post here: 7 all-purpose wardrobe staples worth investing in this spring

Midi dress: Lolë (Runs a little big; I’m wearing an XS. Size down for a tighter fit) Everlane also makes a very similar one for $40! Sneakers: Tretorn (Runs TTS! Available at Nordstrom and Shopbop!)Tote/Backpack: Lolë



Comfortable walking shoes are all the rage for summer

Dress: Everlane (Check out their new version, I’m wearing their old version!) Sneakers: Jack Purcell (they’re old and almost sold out, but I just purchased these leather converse from the Nordstrom sale and I am IN LOVE. They are selling out fast but check back often for restocks–they will also restock them after the sale is over!) Backpack: (Madewell, love this canvas one too) I love this version & this version) Hat:(old from Nordstrom; love this option that’s on sale!)

I think this is my ultimate summer-vacation exploring outfit! You can leave the house all day and feel confident that you can handle anything the day throughs at you. I loved wearing dresses with sneakers all over Italy and a boater hat or straw fedora just adds the perfect touch to look pulled together even after logging miles in the summer heat. A fun bag (or backpack) really elevates a look with sneakers, too. 



Red for daze, Jess dazzles in a red dress and white tennies

See full post here: How to style a little red dress 3 ways for summer 

Dress: B.P. Nordstrom (Runs TTS) Shoes: Tretorn (Runs TTS! Available at Nordstrom and Shopbop!) Belt bag: Madewell (Runs TTS) Sunnies: Ray Ban 53mm Round Sunnies


I love the juxtaposition of pairing sneakers with a miniskirt or dress — it’s so unexpected! I think the key here is all in the accessories, like a fun hair scarf, textured bag or colorful sunglasses. This would be great for an outdoor concert or movie on the lawn. 

An adorable dress and sneaker combination

See full post here: The cutest denim jumper you’ll wear all summer 

Dress: BB Dakota c/o Shopbop (Runs big, wearing a zero) Sneakers: Tretorn (Runs TTS! Available at Nordstrom and Shopbop!) Purse: Amazon (under $20!) Sunnies: Ray Ban 53mm Round Sunnies


Ready for travel! Jess models the perfect get-up-and-go travel outfit

See full post here: How to wear a bodysuit this summer 

Bodysuit: Free People (Available at Nordstrom, Shopbop, and Revolve. Also available in long sleeve!) White jean skirt: (old, but I love this Shopbop option and this longer one from Madewell — on sale!). Sneakers: Tretorn (Runs TTS! Available at Nordstrom and Shopbop!) Belt bag: Madewell (Runs TTS) Hair scarf: Mango



Jess giggles through the crosswalk in a red dress and white shoes

See full post here: How to wear a dress with kicks

Dress: Madewell (old Sneakers:Tretorn (Runs TTS! Available at Nordstrom and Shopbop!) Purse: Amazon White Denim Jacket: (old, love this Everlane version and this on from Free People). 


Cute Summer Outfits With Sneakers  - This feminine outfit is contrasted by these boyish kicks 

Dress: Nordstrom (Sold out; but Reformation makes a very similar one! Also love this pink polka dot version and this Nordstrom one comes in two colors.) Shoes: Tretorn (Runs TTS! Available at Nordstrom and Shopbop!) Bag: Treasure and Bond Jean Jacket: J.Crew (Runs TTS- wearing a size S) 


White sneakers and a denim jacket are staples in every suitcase I pack. (I mean there are very few places where I wouldn’t want to wear a denim jacket and white sneakers ?) They just work with everything and are trusty classics for most occasions — from brunch and sightseeing to museums and concerts


#6 Try White on white

Sneakers can now pair with country-club attire

See full post here: The best linen cropped pants from the feel-good brand you need to know about! 

Pants: Treasure and Bond c/o Nordstrom (Run TTS, wearing size 0) Shirt: Treasure and Bond c/o Nordstrom–(Sold out in straight size but still available in plus! This long sleeve version is nearly identical and fully stocked in straight sizes. Everlane also makes a very similar cotton version!), Sunnies: Ray BanSneakers: Tretorn, c/o (Run TTS!) 


Lastly, I love how chic and sophisticated white sneakers look with an all-white or mostly white look. It makes an outfit exude summer  — simple, easy and breezy! Pair them with your favorite linen button down or even a lace or eyelet dress for a timeless, monochromatic look. 

White on white! Jess strolls down the avenue with white tennis shoes

See full post here: One little white dress, two ways, for any occasion!

Dress: (old — adore this one and this one from Shopbop (both on SALE!) and this one and this one from Amazon!  Sneakers:Jack Purcell (they’re old and almost sold out, but I just purchased these leather converse from the Nordstrom sale and I am IN LOVE. They are selling out fast but check back often for restocks–they will also restock them after the sale is over!) Raffia Tote: Nordstrom (the best beach bag! It’s packable too!) Sunnies: old, similar version here.


There you have it! How do you like to style outfits with sneakers? Which idea is your favorite?

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