The Ultimate Comfortably Chic Travel Outfit

There is an art to traveling while looking cute and maintaining comfort. When I first started travelling, I would always wear clothes that while looked cute, would be sooo uncomfortable during long flights. I once wore a dress on a 10 hour flight with heeled boots. I looked cute but I was basically dead when I landed.

As many of you may know, I travel internationally a lot. I went to Uni in Glasgow, Scotland, but I grew up in Denver. I have moved back and fourth a total of 4 times! yeah I know, a bit much.

BUT this means I am a pro at knowing how to be both functional and cute when flying. I know which clothing articles cause more trouble than they are worth. For example, while I am a proponent of cute boots 24/7, I have learned to avoid wearing such beasts while traveling. They take a long time to take off and put on in security lines, and you end up getting uncomfortable on long fights.

No two trips are the same, but here are some travel outfit picks designed to help you travel comfortably and look stylish doing it:

The Look:

This look is perfect if you have a long day (or night) of travelling ahead of you. This outfit is both functional and fashionable and helps you get from one place to another without too much hassle. This outfit is probably one of my go to choices when travelling.


I always take my coat on the airplane with me. It helps that I travel a lot to chronically cold places, but I like having something warm on the freezing plane during long flights.

Long T-shirt

I love a t-shirt when traveling on long flights. I have my extra layer just in case it gets cold, but when I am running from one end of an airport to another to catch a connecting flight, I can really build up a sweat.

Weekender Bag

I am all for a cute weekender bag. Not only are they super stylish, but they allow for a bit of cheating on airlines as most of them fit the dimensional criteria for a ‘personal item’. Most airlines allow you to bring both a carry on and a personal item for free. I can usually sneak in at least a day or two of extra outfits if need be.

The trick however, is packing them in a way that doesn’t get you stuck at security. I always make sure my liquids are at the top in a clear plastic bag ready to pull out. This always helps me get through security with minimal hiccups.

Cut Out Leggings

Leggings are the absolute best things to wear on long flights. They are breathable, they don’t constrict, and they are so comfortable to travel in. Plus, they look super cute when styled. I honestly wear leggings most of the time I travel, especially if I have to go do things straight off the plane, I still look put together.

Adidas Superstars

I love wearing my Superstars travelling, in fact, I think I’ve only really used them to travel! They are so easy to slip on and off, and in some countries, you don’t even have to take them off at security check points. Not to mention they are so comfortable. These shoes are perfect for a long day of travelling. 

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The Look:

I love this look because it’s a comfortable and chic way to travel. Plus, you really don’t need to change if you are headed straight from traveling to activities, this look is great to wander about new cities in.

Turtle Neck Sweater

Turtle neck sweaters are one of my favorite pieces to layer. They look good with pretty much any outer layer you can find. They also keep you warm and cosy when flying.

Pull on Trousers

So finding good trousers to travel in is a pain. Either they are really cute but constricting, or they are kinda thin and don’t work too well for travel. These trousers look like cute work trousers you would wear out, but have an elastic waist band. They pull over easily and will not constrict during your travels.

Knee Length Coat

So again, coat can double as a blanket during flights. (I am telling you, there is literally no way to stop the cold blast of air on airplanes). The knee length coat is probably one of my favourite looks because it can be worn in so many ways and accentuates what your wearing.

White Trainers

One thing I love about this outfit is the white trainers provide a colour contrast. While I LOVE all black, sometimes it is good to add a pop of another colour. Not to mention, trainers are GREAT for traveling. They are comfy, easy and they can be really cute.

Cute Belt

I am seeing this belt EVERYWHERE on pinterest. So naturally, I bought one. I have been pairing it with almost everything. It adds a bit of bling to your outfit without overdoing it, and honestly dresses this outfit up a bit. Plus, belts while may seem uncomfortable, they are adjustable, so you can adjust them to be more comfortable while flying.

Quilted Backpack

I love traveling with a cute backpack! I mean who likes to run around the airport lugging around a billion things in your hands or slung across one shoulder? I find that on days I know I have a lot of connecting flights and need to be running around from one end of the universe to the other, hands free is really the way to go.

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The Look:

This look is good if you have a shorter flight and need to get going when you land. This is the type of look that I go for after flying home from a weekend holiday. This way, I can jump into all my to do’s for the day without losing more time.

T shirt

Boyfriend Jeans

These are more ideal if you do not have a long flight ahead of you. Jeans can start to get uncomfortable after a while. But for shorter flights where you have to jump into activities, jeans are a great piece to wear. I love wearing my jeans on weekend trips because I can just jump into the day’s activities and not waste time changing. Plus, jeans tend to be a heavier material, so when I am crunched for space on a flight, I wear my heavier clothing to save room.

White Trainers

Okay, so again, trainers are PERFECT for travelling. I literally cannot stress this enough. Especially if you are going to be doing a lot of walking the same day you fly. I can’t count the number of times I wore non-functional shoes, went sight seeing and regretted it for the rest of my trip. Happy feet = Happy sight seeing.

Long Coat

If you are sensing a theme, you are probably right. Long coats are some of my favourite pieces. They can be casual or dressy and again, they are so warm!

Tote Bag

If you are going on a short trip, a tote bag is perfect. You can still carry on most of your travel necessities and they are adorable as well as functional. I always bring a tote bag on weekend trips because I don’t normally need as much space. I like a tote bag with interior pockets though so that I do not have to dig for my travel documents.

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What is your go to piece when travelling?

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18 thoughts on “The Ultimate Comfortably Chic Travel Outfit

  1. I’m definitely all about being comfortable while traveling, so I usually end up wearing leggings, sneakers, and a flannel over a t-shirt. I really like the different mix of outfits you put together though, so I might have to mix it up next time I take a trip!

  2. I am all about comfy cozy travel outfits. Those black leggings from H & M–LOVE! I can’t believe they are $17.

  3. These are definitely super cute outfits to wear on the plane. Unfortunately, I always look like a hobo. I feel like even if I had these outfits on I would make them look “not chic.” Props to all the girls that can travel looking cute!

    1. Thank you! And I feel that way all the time! I think we are all our own worst critic. When I tell my friends they look cute, they always say they don’t feel that way.

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