Travel style: How to plan cute outfits for vacation in a carry-on

How to pack 10 Days of cute outfits in a carry-on bag from Boston travel blogger, Extra Petite

I’ve been getting a lot of questions on what to pack for travel outfits, so wanted to share my “formula” for planning outfits while on the road! I’d follow the same train of thought for planning a capsule wardrobe, for those of you who’ve asked about that. In this post I’ve shared examples of pieces that can be re-styled and stretched into outfits for over 10 days – I can fit all of the above into my carry-on with room left over, which I usually fill with extra items just in case!



Packing Palette // Start by choosing a color palette for your travel outfits, including 2-3 neutrals, and if desired, 1-2 accent colors. Try to pack within this scheme, adding printed pieces in similar color families for interest. Planning and visualizing your wardrobe in categories (tops, bottoms, outer layers, shoes, bag) will make it super easy to mix-and-match the pieces…just choose one from each category to make a complete outfit!
Travel Outfits: Foundation pieces to pack in a carry-on.

Favorite places to find these staples // fun tops // striped shirts // slouchy tees // denim shorts // ankle pants // ankle jeans // maxi skirts // knit dresses

Foundation Pieces – Bottoms // I usually start with bottoms, looking for my most comfortable and wrinkle-resistant bottoms that will work for the destination climate. Dark blue and black jeans are a safe bet, as well as navy ankle pants for a dressier look. Maxi skirts don’t get much love on “what to pack” lists but they are my favorite. Your legs are covered up but can still breathe, plus maxi skirts can be easily dressed up or down.

Foundation Pieces – Tops & Dresses // A slouchy tee and striped shirt are wardrobe workhorses, as you guys have seen on this blog! I also like to add a “fun” top with an interesting detail or two, that can be worn either tucked in or untucked. Mixing a few fashion-forward pieces in a suitcase full of basics will prevent simple outfits from feeling drab.

I’m a dress lover through and through, so I always pack a few with me personally…lace, prints, fit & flare, etc. If I had to just recommend one type for travel, it would be a stretchy knit swing dress for max comfort & versatility.

How to pack in a carry-on! Outer Layers: Jackets and Cardigans

Favorite places to find these staples // denim jackets // oversized cardigans // scarves & wraps // knit blazers // moto jackets // draped trenches

Outer Layers // This will vary based on where and when you’re traveling, but you can never be too prepared for fluctuating weather. For mid-spring, I packed a denim jacket, an oversized cardigan, and a patterned scarf that can double as a wrap. Other outer layers I love for travel include knit blazers, my moto jacket and a draped trench.

What shoes and bags to pack for travel in a carry-on.

Favorite places to find these staples // convertible clutches // cross-body satchels // neutral flats or Rothy’s // low sandals // chic sneakers

Accessories – Shoes // Figure out how much walking you’ll be doing on the trip, and plan shoes accordingly! Colors like cognac brown, tan, or blush are usually versatile and flattering against bare legs. I rely a lot on my Nike sneakers (which typically run a half size small) and neutral flats for their versatility.

Accessories – Bags // Being hands-free is important when sightseeing, so you can enjoy all those ice cream cones and take hundreds of photos. I like to bring at least a roomy tote (good for the airport, shopping, beach, etc), a medium cross-body bag for general use, and a dressier clutch bag that’s also convertible with a strap.

Other (not pictured, but don’t forget these!): sunglasses, jewelry, toiletries, undergarments, PJs

How to pack 10 Days of cute outfits in a carry-on bag from Boston travel blogger, Extra Petite.

Here’s some examples of these pieces mixed & matched to create several outfits! Most of them are very practical for sightseeing, but I’ve noted a few for certain scenarios. As another tip, if I have time while packing, I’ll roughly lay out the possible outfit pairings and take a quick photo on my phone of each set. That way while on the road, I can just wake up and look through the “catalogue” of outfits on my phone and quickly choose one best suited for the day’s activities.

How to pack 10 Days of cute outfits in a carry-on bag from Boston travel blogger, Extra Petite.

Below are two of my favorite pairings…giving me some outfit ideas for the rest of this week!

how to plan stylish travel outfits for vacation

Lastly, here’s some past travel posts where I’m wearing variations of the above outfits:

How to pack 10 Days of cute outfits in a carry-on bag from Boston travel blogger, Extra Petite.

Stylish Travel Outfits | Boston Style Blogger
Both outfit details in this post 

Whew…I hope you guys enjoyed this post! How do you approach packing for long trips? Do you pack your travel outfits in your carry-on? What are some of your must-bring clothing, shoes or accessories?


70 thoughts on “Travel style: How to plan cute outfits for vacation in a carry-on

  • Reply Dressed With Soul May 20, 2016 at 2:22 am

    Wow, perfect! You are a genius in packing and I saved all your suggestions immediately on my phone as packing belongs definitely to the challenge in my life 🙂
    xx from Bavaria/Germany, Rena

  • Reply Claudia May 20, 2016 at 4:44 am

    Incredible! e always want to carry with us tons of clothes, but some basic pieces resoolve always the situation!
    Very useful post!

  • Reply Sasa Zoe May 20, 2016 at 8:35 am

    These are very cute:P

    Shall We Sasa

  • Reply Keri H May 20, 2016 at 10:06 am

    Having a palette in mind while packing is so genius. It's a struggle for my sometimes so these are lovely tips 🙂

    Enclothed Cognition/Bloglovin

  • Reply Unknown May 20, 2016 at 10:11 am

    I love the way he looks at you!

  • Reply Sarah May 20, 2016 at 10:20 am

    Thank you for the great tips, Jean! I'm planning a big trip later this year, and this post couldn't have come at a better time. I'll be bookmarking this post for sure!

  • Reply The Short (dis)Order Cook May 20, 2016 at 10:31 am

    I am trying to get better about packing for long trips so I can take a smaller suitcase when I go away. I have been known to plan outfits for vacation 3 weeks in advance! I think the hardest trips to pack for are ones where you will be doing very active stuff during the day (thus get dirty and sweaty) but know you'll be going nice places in the evening. Your wardrobe gets that much less remixable and you have to change clothes often. Even if your trip allows for minimalism, you have to make sure you have laundry facilities available in case stuff gets dirty or sweaty during the day. I think that's why I always overpack. What if something gets dirty and i have nothing to change into? :-O

  • Reply Carly Mee May 20, 2016 at 10:54 am

    Can you tell us where you got the sandals? I've been looking for a pair just like that! Thanks!!

  • Reply Carly Mee May 20, 2016 at 10:56 am

    Can you tell us where you got the cognac sandals? I've been looking for a pair just like that! Thanks!! (Sorry if this comment went through multiple times, had trouble getting it to work.)

  • Reply Petite and So What May 20, 2016 at 10:59 am

    Thanks for your packing tips!
    Love your outfits featured!!! <3
    Have a lovely weekend

    Julie, Petite and So What?

  • Reply Jenny Ng May 20, 2016 at 11:06 am

    Just what I needed for an upcoming trip!

  • Reply Tanya May 20, 2016 at 11:11 am

    You have the best tips heart emoticon I am all for efficiency because my kids' clothes take up the most of the suitcase space! Love it!

  • Reply Vicky L. May 20, 2016 at 11:13 am

    This is a great guide! Love the versatility between pieces!

  • Reply fabi Aguilar May 20, 2016 at 11:17 am

    Love how you mix everything! perfect outfits 🙂

  • Reply Lindsay Jill May 20, 2016 at 12:22 pm

    I love this palette for spring and summer travel. I want to do something similar for all of my upcoming work trips!

    Lindsay Jill

  • Reply Michelle May 20, 2016 at 12:27 pm

    Where is the scarf from (in today's post, not your travel outfit from a prior post)?

  • Reply Allie May 20, 2016 at 12:36 pm

    Hi Jean,

    I just recently discovered your blog and I love it. I was wondering for this post it looks like you used a closet app? Or did you have to manually remove the background for clothes? I love how your outfits are laid out and I'm hoping to get a closet app to be able to do something similar for my own closet. I was wondering if you had a closet app or know of one to recommend for an Android phone?

  • Reply Vikki May 20, 2016 at 12:46 pm

    Luv this post! Thx for the tips. I have one tip to share for freeing up space in luggage: I have put a smaller bag/purse that I would need on the trip inside the larger tote when in transit. Leaving the zipper of the smaller bag open so that you can still put stuff in there/acting almost like a tote organizer 🙂

  • Reply Camille May 20, 2016 at 1:42 pm

    Wonderful post – this is exactly what I highlight in my blog ( When you pack simple pieces within a predetermined color palette, this makes putting outfits together while traveling so much easier. And the less time you have to worry about what to wear, the more you can enjoy yourself 🙂

  • Reply Rachel May 20, 2016 at 1:51 pm

    Perfect outfits!

  • Reply Patty May 20, 2016 at 2:21 pm

    Sorry this is unrelated to the post, but didn't know where to ask. Why is it that sometimes petite sizes are more expensive than regular? Does anybody know? Is it fair? If anything, they should be cheaper, since it's less amount of fabric. Case in point: VS.

  • Reply Grace @ Brighton+Brinley May 20, 2016 at 2:49 pm

    So perfect! I'm doing a two week Philippines/Japan/Taiwan trip in November and hoping to just bring a carry on. This post is super helpful!

  • Reply Anonymous May 20, 2016 at 3:06 pm

    This post is spot on. This is exactly how I just packed my upcoming trip in a carry-on. I feel that I am not doing a bad job either. 🙂

  • Reply Anonymous May 20, 2016 at 3:35 pm

    Hi Jean! I am in need of a piece of carry-on luggage and I am torn between the Bric's and the DVF. Since you own both, do you think it's worth spending more money on the Bric's? Thanks!

  • Reply KBravo May 20, 2016 at 4:19 pm

    Thank you! I am going on a trip and want to stick to a carry on but I can't decide what outfits to bring-I'm totally copying your list!

  • Reply Jade May 20, 2016 at 5:03 pm

    Is this ASOS skirt see-through? On the website catwalk view it looks like it is. What is your experience with it? Thanks

  • Reply Jenn May 20, 2016 at 5:03 pm

    I LOVE this post. I'll be traveling at the end of the summer so this is really helpful. I may be inspired to do a similar post on my own blog 🙂

    a small bit | bloglovin | twitter | latest post

  • Reply Anonymous May 20, 2016 at 5:44 pm

    Saw some that are almost exactly the same at Nordstrom.

  • Reply Anonymous May 20, 2016 at 6:04 pm

    Love it! Am going to copy it for my next vacation which happens to be 10 days 😉

  • Reply Michele May 20, 2016 at 8:49 pm

    Super helpful! Thanks for the time and effort you put into all your posts!

  • Reply Maria Abad May 20, 2016 at 9:10 pm

    Off-the-shoulder tops and stripes are always my go-to, when in doubt of what to wear, I always go to them.
    MariaOnPoint | Find me on IG

  • Reply Allie Provost May 20, 2016 at 9:45 pm

    i just ordered a suitcase like that and i can't wait to take it for a spin! i love all of these picks!


  • Reply Anonymous May 20, 2016 at 10:06 pm

    What app/software do you use to put the outfits together?

  • Reply Kelly May 20, 2016 at 11:20 pm

    I too would like to know where the scarf is from please.

  • Reply L Breault May 21, 2016 at 12:53 am

    I love this post! I am packing for a 3 week trip to Europe right now and your tips helped me focus! ^_^

  • Reply Lisa Tran May 21, 2016 at 3:44 am

    You are so thorough! Oh my goodness, no wonder why you always look so put-together. Super duper inspiring, Jean!!


  • Reply JulieY May 21, 2016 at 7:16 am

    Great post, thanks for all the effort and details.

  • Reply Anonymous May 21, 2016 at 9:17 am

    great post! try sam edelman trina sandals (courtesy of katherine, for the tote, i carry an ultralight canvas tote from strand books, w/local nyc cache. as for the plane, i tend to wear my workout outfit – zella layered tank w/built in bra, zella live-in capris, running shoes, and grey jcrew long sleeve perfect t – both bc it's comfy, but also bc all the layers shoes take so much space. i haven't worked up the courage to invest in YSL, but so far the tory burch wallet-on-chain has been working wonders. if you're going to a beach, i can't recommend reef ginger sandals, b/c they're comfy and easy to stuff into a suitcase/tote.

  • Reply Anonymous May 21, 2016 at 9:43 am

    I find strapless bras either impossible to breathe in +/- requiring undignified mid-stroll upward yanks. Any recommendations on bras so I can add off-the-shoulder to my collection?

  • Reply Anonymous May 21, 2016 at 10:03 am

    I'm also asking where the scarf is from? It's so pretty!

  • Reply Jael Perkins May 21, 2016 at 11:39 am

    I love all these pieces. Amazing post.


  • Reply Unknown May 21, 2016 at 12:15 pm

    Where can I find the striped shirt and the scarf? Love this post, hope you do more packing posts since I struggle to pack light!

  • Reply  Sarah May 22, 2016 at 5:23 am

    I'm sorry to tell you that the Baublebar codes only work on select pieces. It won't apply to any/all of them on the site. I've tried it.

  • Reply mybeautrip May 22, 2016 at 10:59 am
  • Reply Jean May 22, 2016 at 9:27 pm

    Hi – they are Steve Madden sandals.

  • Reply Jean May 22, 2016 at 9:28 pm

    It's a stock image from H&M; scarf that is old, unfortunately!

  • Reply Jean May 22, 2016 at 9:29 pm

    Hi – I did this manually in Photoshop but I believe something like Polyvore can do it more easily. Sorry I don't have any closet apps to recommend!

  • Reply Jean May 22, 2016 at 9:31 pm

    I've asked about this a few times before and the answer in general is that pricing is based on demand – basically how much inventory is selling and how much is left. So my guess of an example is if an item is selling really well in petites then they may price it higher, whereas if it's not moving in regular sizing then it may be included in sales. The amount of fabric between regular and petite really does not get factored in to pricing.

  • Reply Jean May 22, 2016 at 9:33 pm

    You get what you pay for … the DVF is stylish but it's very inexpensive for a suitcase (when on sale) and feels that way. The Bric's I feel is a high quality suitcase made by a luggage company, so I'd recommend that one if price is not an issue.

  • Reply Jean May 22, 2016 at 9:34 pm

    It's very thin, which is not surprising given the price point. Maybe in direct sunlight you'll be able to see the silhouette of legs a bit through it. It's black though so I don't really have issues with seeing details through the fabric!

Leave a Reply

Your email address will not be published.