Fashion Packing Guides Travel Planning

How To Always Look Cute While Traveling

Everyone has one friend that looks perfect in every single one of their travel photos. From their perfect makeup and hair to their adorable outfit, they are always instragram-ready. Achieving that effortlessly cute look requires a lot more planning than I imagined. Now, as a self-described basic white girl, I enjoy the finer things in life such as starbucks, pinterest, and having the perfect photos to show my friends after a trip. In my recent travels, I decided to make an effort to look cute everyday and achieve thingsose envy-inducing instagram photos. Looking cute while traveling is definitely a challenge, but its not impossible. With these simple steps, you can ensure you always get that perfect travel photo and look cute at all times!king to al

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Plan your outfits before traveling

I cannot stress how important outfit planning is. When it comes to traveling, one obstacle you face in terms of looking your best is a limited wardrobe. Outfit planning allows you to style your outfits for the trip ahead of time. This way you know exactly how a pair of jeans looks with that new top of yours. I also like to pack pieces that can be switched around to create new outfits. This gives me flexibility to get to my destination and change my mind about a particular outfit. I stick to a color scheme so my pieces should be interchangeable and allow me to change things as I please. My favorite resource for outfit planning ideas is Pinterest because there are about a million different helpful pins on there. Check out my favorites here and the example below.

Don’t Pack things you haven’t worn before…

Unless you are sure they will fit the way you want them to. We all fall victim to the desire to buy new clothes for a trip. We want our photos tofeature new looks rather than the same old same old. The risk is not knowing how these pieces will hold up or if they will be comfortable enough for long days. If you want to buy another pair of your favorite jeans, that’s different because you already know how they fit. If you cannot resist the desire to buy new pieces before your trip, buy them well in advance to leave time to try them out before your trip. This is ESPECIALLY important with shoes because they need to be broken in.

This wool skirt(similar here) is one of my go-to pieces and so is the black blouse(similar here) I paired it with.

Invest in key pieces that will work for any trip

We all have those go-to pieces that we pack for almost every trip(dependent on weather of course. This is my must-haves with a few photos and links if I could find them.

  • A good pair of dark jeans. I personally prefer black to dark denim only because I think black jeans are easier to dress up at times. My go-to pair are from Gap because they fit so well and last forever and I really love the style of these Gap jeans in particular.
  • The perfect wool coat- This red wool coat from ModCloth is everything I wanted and more. It is stylish, comfortable and most importantly WARM.
  • Stylish and comfortable boots: As you can see in the photos above and below, I LOVE my Frye Melissa back zip boots.They are cute, comfortable and durable! I highly recommend them to anyone looking to invest in quality boots.   
  • A go-to outfit for nights out! I love a good romper or a mini-skirt and crop top like those pictured below.
  • A maxi-dress that can be dressed up or down as needed. This gorgeous Lilly Pulitzer dress that I have worn to a wedding and just out to lunch with friends is a great example. Its cute, comfortable and versatile for travel. Bonus: the material doesn’t wrinkle!
Similar dress available here
  • A few great sweaters- I like to go with some neutrals and some bolder colors. My sweater collection is well cultivated by this point with a great variety of colors and styles. Sweaters are worth the investment and some great ones I am coveting are: this chunky turtleneck, this cardigan, and this black sweater.
  • A scarf that can go with anything- Scarves are amazing and highly versatile. I especially love blanket scarves like the one featured in some of my above photos and below. This scarf can also double as a blanket to sit on in a park, or a head covering if you visit a church of mosque that requires this. Similar one available here.


You can always dress up any outfit with the right accessories. I highly reocmmend investing in some fun pieces to add to your outfits. Earrings are the easiest thing to transport because they don’t tangle like necklaces. Howeverm if you invest in a good jewelry organizer that problem is avoided! My favorite place to buy accessories is Modcloth because they have a ton of fun options!. Some of my current favorites are these gold map earrings, this map necklace, and these cute floral earrings for spring.

Find a Photographer!

Best way to guarantee a quality instagram photo? Invest in a quality travel partner who will indulge your basic side! My friends are supportive enough to have a full-on photo shoot in the gardens of Versailles, Parc Guell, or Downtown Savannah(pictured below featuring the same great skirt). Having great friends travel with you and take photos or you is crucial! Your friends care more about you getting the perfect picture than a stranger! This ensures you have cute photos to remember your trip by. This is also one of the reasons I prefer to travel with friends rather than solo(more on that here).

If you like following my adventures, check me out on TwitterInstagram, and Pinterest.

From one Misguided Millennial to the world, I hope these tips help you capture the perfect travel photos!


  1. Jani February 20, 2018
  2. Yesenia Morales March 1, 2018
    • Deborah March 2, 2018
  3. Meghan April 10, 2019
    • Deborah April 10, 2019
  4. Heather R Wyatt November 22, 2019

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