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The Golden Girl

Chicago Fashion and Lifestyle Blog

May 28, 2019

How to Style Joggers: 6 Outfit Ideas–From Travel, to Work, and more!

Happy Tuesday! 

Did you have a great Memorial Day weekend!? We definitely did! We celebrated our friends Brian and Annie tying the knot–and then went to the lake house for the remainder of the weekend! 

Today I’m excited to be teaming up with some friends for another Instagram Story Styling Lesson! At 2pm CST this afternoon, I’ll be posting a series of stories on Instagram–going into detail about each of these looks, along with Anna, Connie and Rebecca, who are styling their own looks with joggers! I love doing these little collabs with other blogger friends not only because it gives you guys so much inspiration from other women with different styles and body types, but it also is fun to introduce you to other awesome gals to follow! 

First thing’s first–let’s talk about the featured piece of the day: These joggers! 

Caslon Linen Joggers–$59, also come in petite and plus! 

Sizing: Run big, size down 1 size.

gray joggers and flats

black joggers and flats

black joggers and white sneakers

joggers and sneakers

I got these before my trip to Mexico. I always like to wear something on the plane that is comfortable, but still stylish and respectable. I have a personal rule that I do not wear sweatpants in public. I just think you should dress for the life you want and nobody looks at someone in sweatpants and says, “they look like a respectable member of society.” You never know when you’re going to need to be taken seriously–whether that’s sweet talking an airline attendant or sitting next to someone super important on the plane. 

Thus–that’s why joggers come in handy. Feel like sweatpants, look like real pants–it’s a win-win. I actually didn’t own joggers before this linen pair–again, because they looked to sweatpantsy for me. Then I saw this pair and fell in love! The linen allows you to really dress them up–plus, it ensures they don’t make you overheat in the summer! Great for everything from a beach vacation to a Europe trip, a weekend at home, or a casual, yet polished coffee meeting! 

How to style joggers 6 ways–3 outfits, 1 change of shoes! 

For these looks, I went with three “base” looks, and then a change of shoes to show you how versatile the look can be! You can actually mix and match any of these outfit combinations to create endless variations! 

How to style joggers…from the airplane…

Jess is wearing comfy joggers, sneakers, a striped tee for a little pattern, and a jean jacket! 

This is basically my airplane uniform as of late! Comfy joggers, sneakers, a striped tee for a little pattern, and a jean jacket! 

Striped tee: The one I’m wearing here is super old, but I love this one on sale at J.Crew! Also, this one from Everlane is adorable and only $25! 

Tretorn Sneakers: THE BEST SNEAKERS! They go with everything (even dresses!) and are SO comfortable! They don’t need any break-in! I always wear them on the plane too, because they’re easy to get off and on (unlike a lot of sneakers!) They sold out at Nordstrom but they’re fully stocked at Shopbop (which has Amazon Prime shipping!) Run TTS. 

Jean jacket: This one is also from Everlane! Runs a little oversized, fyi! The perfect top layer for travel–I hardly ever go anywhere without my jean jacket, and it keeps you warm on the plane, too! 

To a casual, but polished breakfast meeting! 

casual outfit

If you work in a casual environment but obviously want to remain polished–this is such an easy way to do just that! Isn’t it nuts what a difference a simple change of shoes makes!? 

Striped tee: The one I’m wearing here is super old, but I love this one on sale at J.Crew! Also, this one from Everlane is adorable and only $25! 

Jean jacket: This one is also from Everlane! Runs a little oversized, fyi! The perfect top layer for travel–I hardly ever go anywhere without my jean jacket, and it keeps you warm on the plane, too! 

Madewell mules: I love these mules because they’re comfortable and add such a “cool” vibe to any outfit! I love the off-white color but the tan or black color would also go well here! Available at Nordstrom, Shopbop and Madewell. 

From a day of wine tasting…

Jess Keys is sharing how to style joggers with white tank

I wish I’d had these pants in Italy, because I totally would’ve worn this outfit again and again! Exploring/Shopping around Positano for example–is what this outfit would be perfect for! 

White tank: Here I’m wearing Everlane’s Air Cami! It’s so lightweight it’s next to nothing on your skin–great for summer! I wore this in Rome on our hottest days in Italy and it saved me for sure. It’s only $22 and comes in multiple colors! If you’re in between, size down. If you want a tank with wider straps, there’s Everlane’s linen muscle tank, or J.Crew’s Linen pocket tank is 40% off right now! 

Everlane Day Sandals: The new sandals! They are A DREAM. The leather is so buttery and soft–you could walk for miles in these and not have one blister! Come in other colors too! They also go with everything, so you’ll wear them day and night! TTS. 

Hair scarf: Head to my instagram story highlights to see how I tie this scarf! I always wear a scarf in my hair when traveling because it makes your hair look way cuter when you don’t want to style it! (Plus, keeps your hair off your face in the heat!) 

…to a day of sight seeing! 

Jess Keys is sharing how to style joggers with sneakers

Just swap your shoes for sneakers, and you’re ready for a day of exploring! You can walk for miles and miles and stay cool and comfortable. (And cute, obviously!) 

White tank: Here I’m wearing Everlane’s Air Cami! It’s so lightweight it’s next to nothing on your skin–great for summer! I wore this in Rome on our hottest days in Italy and it saved me for sure. It’s only $22 and comes in multiple colors! If you’re in between, size down. If you want a tank with wider straps, there’s Everlane’s linen muscle tank, or J.Crew’s Linen pocket tank is 40% off right now! 

Tretorn Sneakers: THE BEST SNEAKERS! They go with everything (even dresses!) and are SO comfortable! They don’t need any break-in! I always wear them on the plane too, because they’re easy to get off and on (unlike a lot of sneakers!) They sold out at Nordstrom but they’re fully stocked at Shopbop (which has Amazon Prime shipping!) Run TTS. 

Hair scarf: Head to my instagram story highlights to see how I tie this scarf! I always wear a scarf in my hair when traveling because it makes your hair look way cuter when you don’t want to style it! (Plus, keeps your hair off your face in the heat!) 

From brunch… 

Jess Keys is sharing how to style joggers

Another perfect travel outfit–especially if you need to stay protected from the sun–linen is THE way to go to stay cool, covered up, and chic! Not going anywhere? That’s okay! This outfit is great for brunch or any leisurely weekend activity at home! 

Linen button down: One of my favorite summer staples and probably the one I’ve worn the most so far this season. The one I’m wearing here is from Lolë–I wore it in this post as well! I love that it’s tunic length so it can be worn long as well, even as a bathing suit cover up! It’s super lightweight and so breathable–it also is great for work! I can’t say enough good things. They are also an ethical, sustainable brand! It’s 100% worth the investment! If it’s not within your budget, check out UNIQLO, they have a linen button down at a steal! 

Everlane Day Sandals: The new sandals! They are A DREAM. The leather is so buttery and soft–you could walk for miles in these and not have one blister! Come in other colors too! They also go with everything, so you’ll wear them day and night! TTS. 

Hair scarf: Head to my instagram story highlights to see how I tie this scarf! I always wear a scarf in my hair when traveling because it makes your hair look way cuter when you don’t want to style it! (Plus, keeps your hair off your face in the heat!) 

…to the office! 

Jess Keys is sharing how to style joggers

Again, CRAZY what a change of shoes can do, right?! These mules took this look from super casual, to polished enough to wear to the office! (If you work in a polished-casual environment, obviously!) 

Linen button down: One of my favorite summer staples and probably the one I’ve worn the most so far this season. The one I’m wearing here is from Lolë–I wore it in this post as well! I love that it’s tunic length so it can be worn long as well, even as a bathing suit cover up! It’s super lightweight and so breathable–it also is great for work! I can’t say enough good things. They are also an ethical, sustainable brand! It’s 100% worth the investment! If it’s not within your budget, check out UNIQLO, they have a linen button down at a steal! 

Madewell mules: I love these mules because they’re comfortable and add such a “cool” vibe to any outfit! I love the off-white color but the tan or black color would also go well here! Available at Nordstrom, Shopbop and Madewell. 

Hair scarf: Head to my instagram story highlights to see how I tie this scarf! I think it’s such a great way to add more personality to your outfit–and also disguise unwashed hair, haha! 

—

That’s all, friends! What do you think? Do you love these joggers as much as me!? Make sure to tune into my Instagram stories at 2pm CST today to get more in-depth styling tips on these looks, and see how my friends Anna, Connie and Rebecca style their joggers as well! 

Filed Under: Outfits, Style

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