Wardrobe Packing Tip

I don’t know about you, but for me, one of the most stressful parts of getting ready for a vacation is figuring out what to wear, and how to fit it all in my suitcase. I always, always, end up feeling like I hate everything I packed, and it’s impossible to remember what shirts I brought and how I can pair everything together into a moderately fashionable ensemble.

This time I had an idea. I would figure out what I wanted to wear by actually dressing up in the outfits. (If I was reallyย ambitiousย I would have paired jewelry with everything but shoes+clothes was enough brainpower the night before we left.) I’d use my iphone to take a picture of the the outfit, and then I would save those photos on my phone as a sort of reference guide each morning whenI was getting dressed. You know that scene on Clueless when she wakes up and has the computer match up her outfit for her? Coolest closet ever! My system worked like a DIY version of that. ๐Ÿ™‚

Here are all of the iphone photos. Doing this also ensured that I had shoes to match AND, very importantly, that I had all of the undershirts/other accessories that I would need.


And now you can see how it all came together. We were gone for about 20 days, and I ended up with only 13 outfit pictures (thank you TH for being patient enough to take all of them!) so there are a few pieces above that I utilized but must not have asked for a picture in. Getting dressed each morning was so much easier than it normally is on vacation, if I felt a bit stumped I’d reach for my iphone and flip through the photos above to figure out what made the most sense based on the planned activities for the day.ย 

We did some shopping in Florence where I was able to pick up some lighter clothes – I hadn’t packed for the very warm weather found in Italy in early September! My wardrobe was perfect for Poland, too warm for Italy.

Oh, and my pretty green bag? It’s by Jenny N. I love it so much, and had a friend help me add a padded camera insert so I could use it as a camera bag throughout the trip. I like it so much better than the Kelly Moore.

Also some nice commenters pointed out I need a new bra. How did I not notice this before? Bummer. Will work on that soon (I believe this is a product of only having one bra (gross of me I know) and wearing it every single day for the past 6 months, barring the times I work out).

110 thoughts on “Wardrobe Packing Tip

  1. I am so glad you told us where you got that bag because I was planning on asking. Off to check out that link…

  2. Um, how did they know you needed a bra?! Anyway, I was ABOUT to ask about the bag before reading through the whole post!! Love the color and the look of it!

    Jenna Reply:

    Some of the more frequent commenters suggested it might be something to look into. They were very nice about it though!

    Marissa C Reply:

    Haha…totally didn’t notice it! I’m surprised you didn’t get one at Nordstrom?

  3. Wow, you were so fashionable on your trip!! I’m super concerned about what to pack for my upcoming Italy trip, especially since it will be colder in November, so pretty much every picture I take will be me in a coat! And I’m kind of amazed at how versatile your green bag is… I would have never thought!

    Were your cute shoes comfortable for all the walking you did there?

    Jennifer @EsqEvents Reply:


    Depending where in Italy you are going it may not be very cold. We spent four days in Rome in January and I wore nothing but a sweater and a puffy vest the whole time ๐Ÿ™‚

    Jenna Reply:

    I spent forever trying to figure out what the temperature would be like! I guessed mid 60’s, and I was very wrong, it was closer to high 70’s. Oops. I picked up some tops for $5 each at Pull and Bear in Florence (the bright ones you see above, and the striped ones) which made things better.

    My guess is you should do pants, boots, dresses with tights, and a medium weight jacket. But I’ve never been there during that time so I don’t know for sure!

    The black wedges are cole Haan, and everything is right in praising them. Super comfortable (I actually shoot weddings in them). The black flats are almost a decade old and I don’t wear them on all day walking trips, but they are fine for 3-4 hours at a time.

  4. You looked SO cute in your vacation pictures!! Adorable! Outfit planning is the only way I travel now! I love not stressing out getting dressed on vacation, knowing I have specific outfits already put together. My favorite color is gold right now, and so my new thing is planning outfits around gold accessories/shoes. On my recent trip, I brought 3 pair of gold shoes (boat shoes, cute flip flops, wedges). They matched everything and worked out great in reducing my shoewear.

  5. This is SUCH a great post!! i’m always totally verklemped about what to pack and usually overpack and yet still have nothing to wear. I also like this idea for work clothes! Thanks for sharing – you look GREAT!

  6. Ahh I remember trying on outfits before bed for school or for a date. Now it’s more like “Is this clean? I’m wearing it.” I think of that Clueless scene ALL THE TIME. I really love your outfit with the long tunic ๐Ÿ™‚

  7. So cute! I like your DIY Clueless closet solution!

    I have always found the hardest part about traveling is picking shoes to wear. I want to wear cute shoes, but my feet hurt SO BAD from walking around that I end up in tennis shoes and even then I’m in pain. Did you walk around all day every day in your little flats in the pics above? Were they comfortable?

    Jenna Reply:

    I try to make sure that the shoes I take with me on vacations like this are pairs I’ve had for a long time and know how they work. I use the black wedges to shoot weddings (they are by Cole Haan) so I know that I can tolerate long periods of time in them. And black flats are like 8 years old (so old I took them to the shoe repair guy to have them resoled) and I don’t wear them on days where we walk a LOT if I can avoid it, but I’ve had them long enough that they are pretty comfortable. I tried to wear the heels twice and wound up with blister both times.

  8. I don’t think I could have thought of a better way to pack. When i travel I bring two suitcases and always end up missing something. I am glad you had fun and the green bag is super cute.

  9. oh jenna! you look awesome! i especially love the striped shirt/running shoes combo! what an inspiration you are!

  10. I’m curious about the camera insert. How did you make it? Is it very bulky? And what brand of shoes did you wear? Flats don’t support my feet very well for long walks (except if they’re Me Toos, love those!)

    Jenna Reply:

    A friend helped me make it using a modified version of this pattern: http://pinterest.com/pin/94022011/. I bought the thinnest foam available.

    I rotated between Cole Haan black wedges (highly recommended) and a pair of flats I bought in London like 8 years ago. I wore the Cole Haan pair when we had a lot of walking to do because they have more support.

  11. I’ve started doing that with my closet, but for work instead! I can never come up with outfits in the morning, and I’m to lazy to come up with them at night. Every once in a while I get the urge to play in my closet and I take pictures of combos I might want to use later! It’s been helpful on those mornings where nothing works ๐Ÿ™‚

    On a random side note… I love that teal(?) zip up jacket!

    Shanna Reply:

    Yes! I want to know where that teal jacket came from! I love the asymmetrical zip.

    Jenna Reply:

    $5ish new with tags at the thrift store!

  12. You look very cute and slender!

    Did you change your hair, though? it just looks different and I cannot put my finger on it.

    Jenna Reply:

    I did cut my hair recently! Added in some layers and gave it much more of a “style” than I had before.

  13. OMG, I THOUGHT your bag was by Jenny N! I have been stalking her store for YEARS and finally decided to pull the trigger and buy one–last night! I love it. Is it the mini or the baby? ๐Ÿ™‚

    Jenna Reply:

    The mini. I found her through Pinterest and I just love her stuff. And I’m so intrigued by her wedding, I hope she posts pictures from it ๐Ÿ™‚

  14. I do the same thing when I pack for trips. For me it’s the only way I can squeeze a weeks worth of outfits into a carry-on bag.
    Oh Jenna! A woman needs a minimum of 2 bras. Your bras, much like your shoes, will last much, much longer if you don’t wear them two days in a row. Your skin will also thank you. I highly recommend nude; it works under everything.

  15. I love this! I’m leaving on vacation tomorrow and was just thinking through what I need to pack and got bummed when I hit the clothing part of my mental list… so excited to go home and pack this way though! You made my day!

    PS I love you in that yellow! You look fantastic and can most certainly pull off the brighter colors! You also look like you are enjoying not carrying around extra wright! It’s been amazing to watch you change in a healthy (and happy) way! Keep up the great work! It shows!

  16. ps: I love the black swoopy belt

    Jenna Reply:

    Isn’t that one fun? It’s dark brown actually, but I found that at a department store in Poland. I love shopping there!

  17. I was one that suggested that you may need better bras. ๐Ÿ™‚

    I only own two bras myself- they’re very expensive if you get good ones! I wear them a few times between washings (I frankly don’t consider that to be a big deal… maybe I’m gross?) to help them last. Both of mine are black though so I’m going to expand my collection to four and get one white, one nude.

    I think you’ll like the way that a new, well-put-together bra changes your figure!

    Jenna Reply:

    Oh I know about the whole new bra thing> And every single time I promise myself I’m going to change and have several and NOT wear them out the way I always do. This time I’ll do it differently I promise!

  18. first and foremost – WOW, jenna, you look so cute and petite!

    i so wish i had cher’s closet technology but your diy version is a great stand in. i am the worlds worst, yet most organized packer. love this idea!

  19. What a great idea! You look amazing by the way! What a huge transformation. Keep up the great work!

  20. You wear a lot of black. Did you buy any new clothes in different colors to even it out?

    Jenna Reply:

    I’ve been working on building up a more colorful wardrobe, but for travel especially I think it makes more sense to have staple pieces (black pants, black dress, black shoes) and build from there so I can pack less (TH and I shared one suitcase for 10 days in italy!)

  21. Ummmm, you look AMAZING! Seriously, very jealous of your wardrobe. Pregnancy is keeping from finding anything cute to wear.

  22. Thank you for admitting that you only wear one bra. I thought I was the only one.

    Jenna Reply:

    Haha, both of us should stop though. Nasty thing to do.

    Samantha Reply:

    I do too :-/. I used to have two but would wear one for a week straight and switch off the next week. One broke last week though and I am too dang cheap to buy another. I have a TJ Maxx gift card I guess I could use for it but I would so much rather use it at Homegoods! ๐Ÿ™

  23. What a good idea! Packing for vacations is way more stressful for me now that I’m a mom, and my last trip I made terrible choices (hello, 50 degree June in Minnesota, meet tank tops). What I love is that you not only made sure you had appropriate pieces for all outfits, but that you had… OUTFITS! I’m the kind of dresser that looks in my closet and says, “Hm, here is a shirt, and here are some pants. Yay me, I’m dressed!”

    Is outfit-building a learned skill or were you just always good at it? And if it was learned, would you mind doing an outfit building for dummies/frazzled mommies post? It seems like many of your readers are very fashionable, but I for one am NOT. ๐Ÿ™‚

    Samantha Reply:

    Oooh! I agree- an outfit building post would be awesome. I am SO bad at putting together outfits. I’ve recently been trolling Pinterest to get ideas but I still can’t do it on my own..

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