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My Favorite Travel Outfit Two Ways

February 24, 2020

Happy Monday! A week from today I’m hitting the road again to visit some family and friends. And that got me to thinking about my favorite travel outfit. I don’t think I’ve shared that with you. Shame on me! So today I’m sharing that easy, comfy look…two ways!

Favorite Travel Outfit Two Ways

When I travel – whether by plane or car or train – I like to be comfortable but also look pulled together. So these side stripe joggers fit the bill perfectly. They are every bit as comfortable as they look, but I think they’re also chic and stylish. These side stripe joggers are the comfy base of my favorite travel outfit.

Venice Side Stripe Joggers

These joggers feature an elasticized pull-on waist band with a flat front, so you can still give you top a little tuck if you prefer. They fit nicely but not uncomfortably snug, true to size. I’m wearing a medium. The lightweight Pilayo® fabric is soft and stretchy, but also thick enough to conceal any bumps or bulges. I feel “covered up” and polished in these, not slouchy and exposed…the way some joggers can leave you feeling. Know what I mean???

Favorite Travel Outfit Two Ways
side stripe joggers (wearing medium) // white ribbed tee (wearing medium) // denim jacket (similar) // Superga sneakers TTS // black leather hobo (more economical option) // link collar necklace // coin pendant necklace

I wore these pants traveling to and from Florida by plane recently just the way I’ve styled them here, except I wore my Adidas running shoes (also available here) and these black socks. While I sometimes wear slip-on shoes, I have TSA Pre-check and don’t have to remove my shoes when I go through security, so lace-ups aren’t a problem.

Oh, and now that I think about it, I also wore this v-neck, cotton pullover…because it was cold when I started my day in Cincinnati. But then I simply pulled off the sweater when I arrived in Jacksonville and slipped it into the side pocket of my suitcase. I wore the black sweater that day, but I also have the pink one.

Side Stripe Joggers

If you’ve been around Dressed for My Day long, you know how much I love these long sleeve ribbed tees. I have a black one, too, and they run true to size. I’m wearing a medium.

I almost always travel with my denim jacket because it’s so versatile. Once I’ve arrived at my destination, whether it’s cool or warm, this jacket works beautifully with dresses, chinos, shorts, everything! So yeah, my denim jacket is often part of my travel outfit.

Favorite Travel Outfit

But I’ve also been known to opt for my black blazer with these joggers, especially if I’m going to need it at my destination for a dressier, business look. This stretch twill blazer, also available in red and navy, is definitely comfortable enough for travel.

Favorite Travel Outfit Two Ways

For this look slightly more down-to-business look, I wore my black leather wedge heel sneakers. These are some of the most comfortable sneakers I’ve ever owned…and that’s with a 2.5″ heel! I think the black leather is extremely versatile, especially for fall and winter, but these wedge sneakers are available in over a dozen colors and patterns. These lighter color sneakers are perfect for spring…and they’re marked down.

Travel Outfit

Back to those pants, just a minute. Notice that the side stripe is very slimming on most any silhouette. And the pockets on these pants are perfect for travel. There’s even a small, inconspicuous zipper pocket on the front.

Zipper Pocket

By the way, when I travel I often opt for one set of jewelry that will go with everything I’ve packed. When I traveled to Florida recently I wore these silver earrings (a gift from my son’s trip to Greece), this link collar necklace and my compass coin pendant necklace. These simple layered necklaces worked beautifully with everything.

Favorite Travel Outfit Two Ways
side stripe joggers (wearing medium) // white ribbed tee (wearing medium) // black blazer // wedge sneakers TTS // black leather hobo (more economical option) // link collar necklace // coin pendant necklace

And that’s how I roll! If the weather stays like it is right now, I’ll undoubtedly be rolling down the highway in these side stripe joggers, my ribbed tee, possibly my cotton v-neck sweater and my wedge sneakers next week. In fact, I’ll probably wear this favorite travel outfit sometime between then and now, too! Let me know if you have any questions about anything I’ve shared today.

Travelling or not, have a lovely day!

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xoxo, Kay
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14 thoughts on “My Favorite Travel Outfit Two Ways

  1. I really like the joggers Kay! Some I’ve had in the past I wouldn’t dare wear out and about. I also like to dress comfortably, but presentable when traveling. Thanks for saying that you have the TSA pre screening pass so that you don’t have to remove your shoes. I really like the outfit you wore last weekend at the women’s conference. It fit in perfectly with the photo booth decor. Maybe the rain will stay away next week while you and your son are in GA. Have a blessed day!

    1. Hi Ginger, Thanks for reading and sharing. Yes, I’m really hoping for some nice weather in Georgia. I know they’ve had sooo much rain. My daughter is very tired of it. My parents escaped it by going to Florida, but I really hope we have nice weather when I’m there. Have a lovely day!

  2. My daughter and I just traveled to orlando Florida to Disney World for the National cheerleading competition Around the first of February , it was the first time I had ever flown. I also wore my gray joggers, black t-shirt and denim coat my black sparkly Tretorn tennis shoes ? . I was stopped and ask several times where I got my cute shoes. Never to old for some sparkle ! Have a blessed day !

    1. Ha! That outfit sounds very familiar!!! Cool. I have a dear friend here in our church who coaches a cheerleading squad in Kentucky and went to the competition, too. Small world! Thanks so much for sharing. I hope you enjoyed your trip!

  3. Now that’s styling around in comfort. I love those wedge heels but I’d still be afraid to wear them. I feel better grounded. Have a great day.

  4. What size do you wear in the v-neck pullover sweater? I’ve never purchased anything from Everlane before and the sweater looks a bit boxy. I’m thinking of sizing down to a small.

    1. Yes, for some reason I bought one sweater in a medium and another in the small. And I wish they were both smalls. Definitely go with your lower size.

  5. Hi, Kay! I’m a new subscriber and want to thank you for your blog and especially for the Scripture at the end of each piece. Evem though we won’t always dress with the same emphasis, we’ll both continue to cling to the Word.==Anne

    1. Thanks so much for sharing Ann. I’m glad you subscribed and are enjoying the blog posts. The scripture portion is very important to me too.