How to Dress Smart & Stylishly for Your Trip

April 18, 2016

Dressing for a Road Trip

I enjoy travelling and since meeting Tom, we’ve been very fortunate to have visited numerous destinations together.  In 2015 alone, we spent about four months out of town. In 2014, I travelled for about two and a half months, some of which involved flying around for trips that were less than a week long.  We take advantage of weekends and holidays to really maximize our travels.  I think we took at least one weekend trip every month and a few times we took four: Las Vegas, Rochester, New York City and Ottawa.  Is there such thing as serial travelling?  I feel like this is what it should be called.

This weekend Tom and I are taking a road trip to San Diego. Short trips are so amazing because it’s always a whirlwind of events.  Even if it isn’t our first time visiting a city, we’ll venture out to find new restaurants and territories we didn’t get the chance to visit previously. The first three things I think of when a trip is booked is the 1) Activities I’ll be doing (since this affects what I’ll pack), 2) Delicious food and 3)  Sites I’ll see.

When I pack, I always place all the things I plan to wear into the suitcase, but pull aside outfits I’ll wear in transit.  At home, I wear sleepwear and track pants, but when I go out, I want to still look like I’m dressing with a purpose.  While traveling between destinations, I’m still representing who I am.  At airports, I sometimes find myself meeting really interesting, intelligent people with cool stories.  These people can be seated by you waiting for a flight, next to you on the airplane, at the airport bar, or if you’re doing a road trip as I am, anywhere you stop for a bite, and the first impression I do not want to make is: I’m too lazy to care.  Wearing something nice doesn’t mean it has to be uncomfortable.  Usually the items I wear in transit work with pieces I can mix and match with in my bag.  Here are ways you can be smart, stylish and comfortable between destinations.

Lifestyle Fashion Blog Road Trip

1) Athleisure

The athleisure trend is a combination of mixing sporty with casual chic. This usually means wearing really nice and stylish athletic pieces.  Some of these pieces would have beautiful cuts and patterns that you’d find in some of your own working wardrobe. I’ll admit that when this trend first came out, I was not quite ready to commit.  Lululemon, the trendy yoga brand, is a Canadian label that grew popular very quickly way before it went to the United States or anywhere else in the world, and when I was living in Toronto I was not willing to be one of those people who wore yoga pants to the office.  In the following few seasons, luxury brands and designer labels presented some beautiful jackets and  tailored athleisure ready-to-wear pieces now worthy of your wardrobe. These trends have even trickled down to affordable brands you’ll find at your local mall or at your favorite online retailers.  Kate Spade made a few athleisure pieces in a collaboration with Beyond Yoga here and even Chanel has been making sneakers!

2) Classic & Comfortable

Loose cardigans that go over classic tees and breathable pieces are great options, especially with some stretch because they won’t wrinkle and will allow you to move around comfortably even in compact spaces.  Sometimes it can be a challenge if you don’t want to wear trousers or jeans because you can feel constricted or kind of a squeeze at the stomach, so understandably it’s not ideal for long distances.  When I’m flying to a warm destination, I often wear well-tailored maxi dresses or long skirts.  They flow away from the body and still keep your legs warm in flight.  For colder destinations, I like wide leg or palazzo pants.

How to Dress for a Road TripDress for a Road TripHow to Dress for Road TripsHow to Dress for Long RideHow to Dress for a Short Road TripStyle Llifestyle Blog Dressing for a Road TripHow to Dress for Road Trip Carry On

3)  Trendy in Cozy Cuts

When I was about 13 years old, I was a tomboy who got selected to go to sports camp. It was during that young awkward stage in my life where I had a short-lived crush on a boy started and felt a little more feminine.  This lace top and bomber jacket combo is a reminder of that time in my life. Bomber jackets, off-the-shoulder tops and lace are among some of the trendiest items this season.  I recently picked up this one for cooler days and chilly evenings.  It’s versatile because its design is simple and can be worn over many different pieces in my wardrobe.  For this road trip, I decided to pair it with a loose pair of jeans with some stretch.

Since this is a road trip and I’m not walking around an airport, I decided to wear the heels that I planned on mixing and matching with other outfits on this trip. Ultimately, I choose to dress  comfortable, yet stylish so that I can relax, unwind and stay warm in my seat for long periods of time.

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I also love light, stylish pieces of luggage.  It took me forever to find one I fell in love with and this set by Diane von Furstenbery stole my heart.  I just had to buy the set.

How do you dress when you travel? What are your own favorite things to wear when you’re sitting for long periods of time in transit during road trips or flights?  I’d love to hear!

You can also follow me on Bloglovin♥, find me on Twitter or Instagram.



Outfit: Bomber Jacket from Coach.  I can’t seem to find it online anymore.  If I do, I’ll post it, but this is a similar one at Asos. Jeans & Heels (old) by ZARA. Diane von Furstenberg Adieu carry-on available here. Faye Bag by Chloè available here.

Photo credit to my one and only, Rise Again BJJ

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  • Amy April 18, 2016 at 5:04 pm

    Love this outfit, definitely stylish! Loving those jeans.

    Amy Ann
    Straight A Style

    • miki April 25, 2016 at 10:05 am

      Thanks Amy!

  • Jessica April 18, 2016 at 7:13 pm

    I’m loving this outfit and your tips! Your luggage is amazing too!
    Jeans and a Teacup

    • miki April 25, 2016 at 10:10 am

      Thanks Jessica! I’m obsessed with the luggage. It’s nice to feel like they’re part of a pretty bag collection now! 🙂

  • Mica de Leon April 18, 2016 at 7:38 pm

    Lovin this look! Definitely something I can wear for a trip as well.

    There’s More to Mica //

    • miki April 25, 2016 at 10:23 am

      Thanks! Kind of obsessed with good jackets and lace.

  • Pam Hetlinger April 18, 2016 at 8:28 pm

    Love the details! I’m always a big proponent of carrying a big purse or beach bag as my second carry-on. But that might be because I have too much stuff!! xo, Pam

    • miki April 25, 2016 at 10:30 am

      I know what you mean! Especially when I am flying for a longer trip, I’d grab a bigger bag to carry an Ipad mini, magazine and a camera around! Luckily with road tripping all the luggage and extra bags just go into the trunk. haha


  • Leah April 19, 2016 at 5:21 am

    Amazing travel style! I have that piece of luggage in brown, and I am obsessed with it. Also, so obsessed with you cute jacket!!

    xx Leah/

    • miki April 25, 2016 at 10:45 am

      Thanks Leah! I love the luggage. I meant to get brown because they won’t look like they get dirty quite so easily, but I loved the white and stuck with it. 🙂 No matter what color, I love the style.

  • Rai April 19, 2016 at 5:55 am

    I’m traveling next year and it will involve very long flights (basically anywhere out of Australia is a long flight haha) I wish it was acceptable to wear pj’s on the plane haha I like the idea of the skirt as its not restrictive, anything that can make me feel less claustrophobic is a win in my books! I love you suitcase here its gorgeous! The whole outfit is perfect for a long drive. I don’t think I could ever wear jeans on a plane though haha!

    Rai |

    • miki April 25, 2016 at 10:43 am

      Haha. I don’t blame you! Unless I’m wearing really stretchy jeans, I tend to wear a long dress with a long scarf or a good jacket for my flights! 🙂 Those airplanes get so cold!

  • taislany April 19, 2016 at 7:56 am

    Wow, love this outfit!!

    Happy Tuesday! Kisses,
    BLOG | Taislany

    • miki April 25, 2016 at 10:48 am


  • Kelsey April 19, 2016 at 9:30 am

    super chic style! I love how you talked about wearing presentable clothing during travel because you represent your self! love the way you think! fantastic post!

  • Laura April 19, 2016 at 9:34 am

    Doing short trips is something I would like to do more! So many great and fun things can happen and it’s not too hard to plan.
    When I’m travelling I also like to make an effort in choosing my outfit. I often go for loose bottoms because it’s much more comfortable.


    • miki April 25, 2016 at 10:52 am

      Definitely would recommend doing more trips! I love them so much and you don’t need to spend a fortune to have fun! 🙂


  • Brown Eyed Toast April 19, 2016 at 6:28 pm

    Love love love your travel look babe! I just covered my travel essentials on the blog- it seems travel is on everyone’s minds lately! I also love that gorgeous bomber and this athleisure look. Comfort is always #1 in my book, and I love how you achieved it with so much style! xo

    xo Soo |

    • miki April 25, 2016 at 11:00 am

      Amazing! 🙂 I love that you’re a huge traveller & so awesome to see how other worldly stylish women pack! 🙂


  • Konstantina Antoniadou April 20, 2016 at 6:18 am

    gorgeous travel look

    • miki April 25, 2016 at 12:03 pm

      Thanks so much! 🙂

  • Dominique April 20, 2016 at 9:06 am

    This is such a stylish look and LOVE your suitcase! xx

    • miki April 25, 2016 at 12:06 pm

      Thanks! I’m kind of obsessed with it too. So happy when I take it out to travel around!

  • Emilia Isa April 20, 2016 at 9:12 am

    I really love your outfit. Classic, beautiful and modern ! 🙂

    • miki April 25, 2016 at 12:07 pm

      Thanks for your sweet comment, Emilia! 🙂

  • Lizza April 20, 2016 at 5:17 pm

    Nice look!

    xx LL

    • miki April 25, 2016 at 12:08 pm

      Thanks Lizza!

  • AMANDA April 21, 2016 at 7:09 am

    In love with your shoes! Great look<3

    • miki April 25, 2016 at 12:09 pm

      Thanks so much Amanda! 🙂

  • Kristen April 21, 2016 at 8:30 am

    Love this look! Casual and stylish. I’m from San Diego so I hope you enjoy! XXX

    • miki April 25, 2016 at 12:11 pm

      Thanks Kristen! 🙂 I had a great time. I’ll have to do a post on SD soon. 🙂

  • adele miner April 21, 2016 at 3:31 pm

    Perfect, thanks for sharing this! I would love to follow each other, let me know if you would too x

    • miki April 25, 2016 at 12:14 pm

      Thanks! 🙂

  • yuka April 21, 2016 at 10:53 pm

    great tips! I always have the hardest time packing for trips. I totally see why you had to take the plunge on the luggage, it fabulous!

    • miki April 25, 2016 at 12:15 pm

      Thanks Yuka! 🙂 Packing for trips is like a talent and art! lol

  • Carmen April 22, 2016 at 12:52 am

    Gorgeous look! I love each detail of it – the shoes are amazing. The jacket is so perfect for traveling 🙂
    xx, Carmen –

    • miki April 25, 2016 at 12:17 pm

      Thanks Carmen! 🙂

  • Marsya Aulia rizkita April 22, 2016 at 2:54 am

    Super love with your style!
    You’re so pretty. And thanks for sharing your tips:)

    Don’t forget to visit me back,

    • miki April 25, 2016 at 12:19 pm

      Thanks Marsya for your sweet comment! 🙂

  • The Fashion Folks April 22, 2016 at 7:39 am

    Love to wear jumpsuits, they’re might not be the easiest to travel in but yet so comfortable and fashionable! Love your outfit btw, the shoes are great! Xx

    • miki April 25, 2016 at 12:21 pm

      I love jumpsuits too! Such a great option. 🙂

  • maray April 22, 2016 at 9:58 am

    Great post! I like your jacket ♡ Kisses!!

    • miki April 28, 2016 at 12:37 am

      Thanks Maray! 🙂

  • Marie April 23, 2016 at 1:12 pm

    Such an amazing post ! You looks so gorgeous. I really love the bomber jacket.
    Hope you will have a great weekend.

    • miki April 28, 2016 at 12:35 am

      So sweet of you! Thanks for stopping by!

  • vera April 23, 2016 at 7:57 pm

    Such a great post, you look AMAZING!!

    Blonde in Cashmere

    • miki April 28, 2016 at 12:39 am

      Thanks Vera! 🙂

  • PutAllOnMe April 24, 2016 at 6:11 am

    Great tips girl, thanks for sharing!
    I have to say that I am obsessed with this look, everything is so on point! I can’t even decide which piece I like the most – this is totally my style 🙂

    • miki April 28, 2016 at 12:49 am

      Thanks so much! 🙂 So awesome. Great minds think alike!

  • The Sunday Mode April 25, 2016 at 5:02 am

    This post was timely, I’m going to be travelling quite a bit this year and it’s always great to hear new ideas. Also, I think that luggage is really unique and will make it so much easier when you have to try to spot your bag from others at the airport baggage claims 🙂

    • miki April 28, 2016 at 12:50 am

      Thanks! So glad you enjoyed the post! I think a lot of people choose darker suitcases, which is a good thing when you’re checking in your bags a lot, but I fell in love with these. 🙂 If you pick up a new bag or add something to your luggage, please share. I’d love to see what you end up with, too! 🙂

  • Cissy Tang April 26, 2016 at 4:36 am

    Your post caught my attention as I am getting near to start my 16 day cruise in Mediterranean. Needless to say packing the right wardrobe is one big item on my list. Thanks for the great ideas, and I always spend considerable time pre-thinking what I should bring. Your tips definitely match to some of the ways I make decision on my travel outfits. I also try to (where possible) take into consideration of the locations I will visit and preview some of the pics ahead of time (thanks to this amazing thing called Google images). If the location is an old ruin, like Ephesus or Giza pyramid, then I will pick an outfit that is brighter in colour or even go the other spectrum to dark or black for a contrast. For Santorini or Mykonos, I will avoid blue/white combinations. The last thing you ever wanted is to be blended or camouflaged by the surroundings in your photos.

    Talking about luggage, I love Rimowa’s Salsa Air, light weight, stylish and with amazing selection of colours. I have never owned a luggage in black, navy blue or dark grey, because you will have a hard time identifying it on the luggage conveying belt in an airport.

    Keep posting great fashion trends and tips. Love it!

    • miki April 28, 2016 at 12:53 am

      So jealous of your Mediterranean trip! Sounds amazing! Yes, go for bolder colors or bold patterns. It would look amazing against the backdrop! Especially when you’re going somewhere sunny with white everywhere like Santorini and Mykonos. I can’t wait to see all the pictures from your trip! I’m doing a post on how to pack for a big trip soon. 🙂 Hopefully it’ll be before your trip!