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As we gain travel and life experience, we pick up valuable lessons along the way – our point of view on packing, clothing, and shopping may completely change. That’s what happened to one of our readers (now a TFG team member).

Read on to discover her journey transforming from fashionably challenged to travel style savvy!


Travel Style Evolved

Written By: Kelly O’Laughlin


Since I started reading this blog and the TFG Facebook group around 5 years ago (plus what I’ve learned from my own experience traveling in 35 countries), I’ve made a lot of changes and discoveries that have allowed me to feel more put-together, confident, and comfortable while traveling.

I’m excited to share these packing and style tips with you!

Before I start, keep in mind that we all have different styles and tastes, so not everyone might agree with my tips. Additionally, I’m in my mid-30s, so if you’re much younger, you may feel differently, too!

Let’s get to it:



Stylishly functional travel clothes: Anatomie | Vacay Style


Don’t buy technical “travel” clothes for your trip


One thing I was shocked (and relieved) to learn was that Alex—the founder of Travel Fashion Girl—made the same mistake as I did. Even she packed and wore unstylish “travel” clothes on her first trip! Can you believe it? I thought I was the only one! It turns out this is a common error made by first-time travelers.

Before my first RTW trip in 2003, I spent lots of time at sporting goods stores and on travel gear websites buying “travel” clothes. I focused on brands like The North Face, Columbia, REI—you get the idea. I even bought a pair of ill-fitting zip-off convertible pants!

The clothes I chose were downright ugly and inappropriate for the type of travel I’d be doing.


These are the best travel pants for women!


Now, don’t get me wrong. There are times when technical clothing and convertible pants are useful and necessary, like if you’re jungle trekking or mountain climbing or something like that. But I was not doing any adventure activities!

Here’s what I ask myself now: What are locals wearing? I was walking around Chiang Mai, Thailand, in zip-off pants while locals were wearing normal clothes! Why did I need special pants just to walk around a city?! It feels silly to think about it now. I could’ve worn normal clothes.


Here’s a roundup of alternatives to traditional travel pants!




Inseam Pant | T-shirt


That said, adventure clothing brands have come a long way since my fashion faux pas over 10 years ago; now there are some better-looking options for convertible pants and travel clothes.

But the lesson I took away from my experience is this: unless I’m participating in hiking, camping, sports, or otherwise specialized activities, then I don’t need special “travel” clothes from sporting or outdoor brands–even in humid, hot weather!

Cotton, linen, rayon, and silk are great in the heat. That leads me to the next tip…




Shirtdress | Lace-Up ShirtdressT-Shirt Dress


Dresses are the best for hot, humid weather


My personal favorite hot-weather outfit is a solid-colored (probably black), not-tight, almost-knee-length dress in a non-wrinkling, lightweight fabric. This is my absolute favorite for staying cool—plus, dresses are never sloppy and usually look nicer than shorts.


Read this to find out the best fabrics for travel!



1st Outfit: Dress | Cardigan | Shoes | Bag | Sunglasses | Necklace | Watch
2nd Outfit: Dress | Shoes | Clutch | Belt | Earrings | Bracelet | Lipstick
3rd Outfit: Dress | Shoes | Scarf | Bag | Hat


I can wear it with or without a belt, a scarf around my neck, a cardigan, or dress it up with jewelry. I can wear leggings if it’s chilly. It can serve as a swimsuit coverup, too.


Find out how to turn any of your dresses into a versatile dress!


Yet another benefit is that a dress made from thin, opaque fabric will dry rather quickly when I hand-wash it. (Although finding a lightweight fabric that’s not see-through can be tricky!)


Shirtdresses are easy-to-wear outfits for travel. Find out why as I show you how to wear a shirt dress on vacation!




Midi Skirt I Mini Skirt


I love skirts for the same reason. However, a skirt has one advantage over a dress—it doesn’t need to be washed as often.

Let’s be real: tops (this includes dresses) need to be washed after every wear, and a skirt can often last a few wears without washing. That’s a huge benefit. Just wear the same skirt every day with a different top!




Floral I Drape Front


Lastly, if you don’t like dresses, try a romper. There are cute, lightweight styles that will work well in the heat and can be dressed up or down.


Shop our round up of the best summer rompers for travel!




Clothesline | Sink Stopper


Pack less


I love the convenience of hand-washing clothing in sinks at hotels and AirBnbs. It’s so easy! If you wash an item every night, you could wear it over and over, and that means you don’t need as many clothes. Imagine: instead of bringing 7 tops for a 7-day trip, you could bring 2 or 3.

For me, washing clothes was the key to packing lighter. If I pack items I love that are easy to hand-wash, I know I’ll be happy wearing them every other day or so.


Read these tips on how to hand-wash clothes while traveling!


Also, remember that you can buy anything you need almost anywhere you go. If you run out of shampoo, buy it. If an unexpected cold front comes in and you didn’t pack anything warm, then buy a sweater or coat. It’s better than packing the kitchen sink.

Along the same lines: don’t pack “just-in-case” items.


Take a look at this printable packing list which can help you pack for any vacation!




Hat | Cardigan | Shirt | Sunglasses | Shorts | Bag | Shoes


Totally plan out all your outfits before packing


  • How I packed in my younger years: I count the number of days of the trip and bring that many tops. Pack other clothes that seem appropriate for the weather. Show up at the destination and stare in disbelief at the random, mismatched items in my suitcase.


  • How I pack now: I write down everything I’m thinking of packing for the anticipated weather and activities of the destination. Then I think about each item and whether it matches everything else, can be layered, and is multi-purpose. I lay everything out and try on outfits if needed. I don’t bring items that serve duplicate purposes (i.e., two warm sweaters). This process can take time!


Start preparing for your travels as soon as you book your trip!


Creating a capsule wardrobe might sound easy, but it’s tricky to find the right combination. But when you find it, it feels good.



Compass Rose Compression Packing Cubes


Use packing cubes


It wasn’t until I actually used packing cubes that I realized how great they are. You can really pack your clothes in tightly, saving lots of space. It makes my luggage feel so organized!

Also, learning about slim packing cubes vs. non-slim cubes was a game changer. I’d had large packing cubes for years and never liked them or used them. I bought the “slim” version and they work so much better because they maintain their cube shape even when stuffed.


Watch the packing tutorial on Youtube!


In 2017, I launched Compass Rose Travel Accessories and my very first product was a 4-Piece Set of Carryon Packing Cubes. These are the only packing cubes sized to fit the exact width of a carryon suitcase and they also have a unique color-coded and numbered organization system – the only kind currently available anywhere on the market.

I put together a five-part YouTube series showing you the different methods to use packing cubes. If you use this specific packing strategy, they can also compress your belongings. This is the secret to traveling carryon only!



Invest in higher-quality clothing and shoes rather than cheap stuff


I guess it was how I was raised, but for most of my life, I always bought clothes on sale and from outlet malls. I focused on price and not whether the item looked and felt perfect. That led to a lifetime of not-quite-great attire.

I remember planning a trip to Egypt many years ago and I was worried about how hot and humid it would be. I went to a sporting goods store and bought a name brand, moisture-wicking, button-up top–on sale–that was the ugliest bright salmon-pink color you could imagine.

I would have been better off paying double for a normal color that looked decent! (Or, of course, not buying that technical shirt in the first place!)

Now I remind myself not to buy things unless I instantly love how they look and feel on me–not just if they’re on sale. If I don’t love something, I shouldn’t try to convince myself to love it. I need to be patient and wait to find the right item. There are so many clothing options out there; don’t settle for something that’s not quite right.

Spending more on a quality item I adore is worth it. I ended up wearing that ugly salmon-colored shirt once then tossed it. The photos I took wearing it in Egypt aren’t flattering. That leads me to…


To help you in your travel preparations, we’ve put together a list of the best online shopping sites!



Sunglasses | Hat | Bracelet | Shirtdress | BagFlats


You’ll cherish your travel photos forever, so why not look nice in them?


I look back at photos of myself taken in front of famous sites around the world and wish I’d dressed a wee bit nicer. It seems superficial, but it’s not that difficult to put in a little effort and planning and to look nicer, at least for photos you’ll cherish forever.

The first time I visited the Sydney Opera House in 2003, I got my photo taken while wearing an ill-fitting sporty shirt I’d purchased on sale, along with the shorts from my convertible pants! I was always disappointed that I looked so sloppy in my photos in front of this iconic building.

Fortunately, I got a second chance to make a first impression. Ten years later, I found myself in Sydney again and made a point to do my hair and wear my favorite (full price from Nordstrom) cashmere cardigan! Those were photos I wasn’t embarrassed to share!

Unlike buying ten cheap tops, when you shop for quality then you only buy the one perfect top using the capsule wardrobe method to make more satisfying outfits with less pieces. Learn how capsule travel wardrobes work.

Even if style and fashion aren’t your strongest points (like me!), there’s no reason they can’t be fun. Fashion is functional, of course, but it adds spice to life, too! And the old saying is true–when you look good, you feel good.


Find out the best pair of travel pants that female travelers all over the world are raving about!







Need help creating a capsule wardrobe?


Savvy travelers know that a capsule wardrobe is the secret to traveling carry-on only. Pack Light Stylishly is our eBook that shows you exactly how to make a functional yet stylish capsule wardrobe for travel.


Learn more about Pack Light Stylishly here!



Do you feel like you are fashion-challenged? What packing tips have you learned over the years? Share in the comments below!


For more capsule wardrobe tips, please read:






I hope you liked this post on packing and travel style tips for the fashion-challenged! Please share with your friends on Facebook, Twitter, and Pinterest. Thanks for reading!


Author Bio: Kelly O’Laughlin is the Managing Editor of Travel Fashion Girl and has visited over 35 countries. She also runs the blog and podcast “A Highly Sensitive Person’s Life”. Kelly is based in Southern California.