How to dress stylishly and comfortable while traveling

o you dress up or down while on vacation? Wear less or more makeup? I dress up more, and I wear more makeup – except on the long travel day on the plane, I go sans makeup. I am motivated and excited to explore, feel and look my best while exploring an epic location. I do this because I know I’ll be taking photos anyway and just incase I want a photo to remember it, I don’t want to be in athleisure or looking like I do every day. I don’t have to be totally extra, but I can be, and you can be too!

When I was in France for 10 days with my best friend Michelle she told me I needed to write a post about how to pack warm, comfortable and stylish. She was impressed with what I wore and knew I was warm – except for that one night in Switzerland it was below 30 and I was starting to get sick and I was miserable. But other than that, I did well for 40-50 degrees!

how to dress stylishly and comfortable while traveling - traveling tips

Packing for comfort and style

  1. Bring comfortable stylish shoes – They don’t have to be workout shoes, in fact, I’d say skip those and check out FitFlop – they are ergonomic and adorable. Luckily white sneakers are in so you can wear them with anything, even a dress! If you need to pack stylish shoes that aren’t comfy add an insole, it’s worth it, even a cheap thin one from Target works – I did it for my knee high pointy boots that felt like cardboard and it instantly made it comfortable!  Also, if it’s cold temps, knee high boots will really keep you warm.
  2. Pack fleece lined leggings to go under skirts or loose pants (like faux leather paper waist pants) – If it’s cold where you are going, pack a black and nude pair. I bought these on Amazon. I layer it under skirts – skirts with tall boots or long skirts are the way to go. Pleated is an elevated look. And yes, pack skirts.
  3. Bring a statement piece – My statement piece was a leopard coat. You can go for gold sneakers, or statement earrings!
  4. Pack colors – Colors look great while traveling, it can make you pop especially if you are going to Europe that can be more grey with the weather and stone buildings. If color isn’t your thing, consider a colored scarf. Red is my favorite color that pops.
  5. Have fun with accessories – I packed two French berets. No one in France wears berets, the tourists do, lol. But gosh I had so much fun and why not? Go with the theme, don’t worry about what other people think – if anything they probably think you are so cute and remember, you’ll never see them again. Have your fun and take your photo. If it’s raining, pack a clear umbrella it looks better in photos.
  6. Warmth – Dressing warm can sometimes be a little harder  –
    1. Fleece lined leggings under skirts or looser pants.
    2. Flat knee high boots
    3. Long coats (that reach you to your knees)
    4. Ear covering accessories like knit headbands or hats
    5. Henley or layering shirts under more fashionable tops

Lastly, how to look good in travel photos (original post)

  1. Pack like a stylist
  2. Think like a photographer
  3. Pose like a model
how to dress warm and stylish while traveling for photos
how to dress warm and stylish while traveling for photos

rhinestone sneakers shoes Michael kors MICHAEL Michael Kors Allie Wrap Trainer Sneakers^^Michael Kors rhinestone sneaks – cute but I am adding insoles.

I was comfortable wearing leggings under skirts, it kept me warm and long skirts are glamorous. Ladies stopped me to tell me how chic I looked (in France!), and a beret was a fun touch. So don’t forget the hair accessories. Layers like a thermal top under sweaters provide additional warmth.

Also fabric headbands keep ears warm on cold windy days. In this photo below I’m wearing layers! A thermal top and fleece leggings. I will say my little ankles were cold so that’s what I didn’t love – so if you can cover as much as you can on your body when it’s cold you’ll be much more comfy!

how to dress warm and stylishly and comfortable while traveling - traveling tipshow to dress stylishly and comfortable while traveling - traveling tips

And if you’re at all hesitant about wearing something that will make you stand out, like a pink tiered tutu, wear it anyway. Because how often are you going to find yourself on the other side of the world at Versailles?

how to dress stylishly and comfortable while traveling - traveling tips versailles France pink tutu

Diana Elizabeth thought she’d leave the tiered pink tutu in France after wearing it once but then she also just thought, why not bring it back home, only she needs to figure out when to wear it again.


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Diana Elizabeth Steffen setting the table for her annual garden party


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Diana Elizabeth is an author, photographer, and obsessive thrift shopper. You can typically find her in the garden wrist deep in dirt, at a local estate sale or planning her next creative themed party. She continues to blog weekly.


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