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 really ambitious 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. :)

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. 

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 :-)

    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.

    Gogo Reply:

    I spent a week in Florence and Milan in the early spring a couple years ago. It was definitely cold some days, but not bad. I think it was warmer in Milan.

    I brought this navy blue wool coat I have. It’s belted, hits mid thigh, and works well with casual and dressy looks (as is the case with this type of coat). Then layers. Sweater or two, long or 3/4 sleeved shirts. That way you can layer up or down as the temperature changes through the day or between day. Plus what Jenna said about bottoms.

    If you want good, basic flats for walking check out lands end heritage flats. I wear them all the time mine have yet to wear out. Rubber sole protects from water seepage and slipping. In the winter though, you’ll want at least one pair of shoes you can wear socks with and boots if you have them. But not snow boots – at least not in the city.

  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 :-)

  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.

    Ashley Reply:

    Thanks Jenna. I think my whole problem is that I get caught up in getting new things/shoes/clothes/etc. for trips and then I end up with shoes that make my feet fall apart. I will have to work on breaking in a tried & true, comfy but cute pair to wear the next time we’re planning a trip.

    Natalie Reply:

    I travel almost exclusively in TOMS. That’s really the only time I wear them! They are so comfortable and the leather ones (not the vegan ones) have a great arch support!

  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 :)

    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!

    Shanna Reply:

    Was there a tag? If so, what brand?

    Jenna Reply:

    It’s by tresics

  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? :)

    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 :)

    Jess Reply:

    Awesome! I ordered the baby because I thought the mini might be too small but it really isn’t. It’s hard for me to judge proportion when she models the bags because she’s so ridiculously tiny. Anyway, gorgeous bag. I got the black because I was too in love with the eggplant she sold out of ages ago to pick another color. :)

  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.

    ADoyle Reply:

    I agree about the nude bra, it doesn’t show under clothing like white bras sometimes do. In fact, nude is the closest color to white I’ll wear in my bras.

  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. :)

    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!

    Dawn Reply:

    From one big bosomed girl to another :) I get the new bra thing. It’s horrible. I hate it. And then one of MY friends said I needed to not wear the same bra (I’m guilty of exactly what you do!!!) over and over and over and blahblahblah. She told me to check out Lane Bryant. OMG! LIFE CHANGING! I actually LOVE my bras now. And if you sign up for their emails on their website you can catch good deals, too. They’re slightly more expensive, at around $32 a pop full price, but that’s not as bad as Victoria’s Secret, which I have never liked a bra from, and they are cute, fit great, and are made for us big bosomed girls. Just thought I’d throw in my two cents. :)

    Meg Reply:

    I don’t think Lane Bryant would fit Jenna (as an avid Lane Bryant customer). I say this because thought I think the cup size might work, I think she’s too small for the bust (is that what they call the number?)

    Senora H-B Reply:

    I have had a lot of luck with Bra Smyth. They are online and have a really fantastic selection.

    Jess Reply:

    It’s too bad the Euro trip didn’t include a trip to England because Bravissimo is awesome and a life-changing experience. An entire store dedicated to those of us with size Ds and above! Once you have the right size, it’s fairly easy and painless to order from them online. :)

    Erin Reply:

    Hi! I have an ample bust as well and have to say that the only time I’ve walked away with a great-fitting bra is when I’ve shopped at Nordstrom and been measured. I’m now convinced that is critical. The salesperson was SO helpful and brought me multiple styles to try on. It can be expensive buying a bra that fits well, but it is so worth the money. I willingly fork over $75 now so that I don’t have to constantly fidget with my straps. It is heavenly walking around with my bosom sitting high! (I personally love Le Mystere and Freya. The Freya line has a great sports bra as well.)

  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!)

    Jess Reply:

    That makes a lot of sense. Black tees and jeans are a staple for me for traveling and then mixing it up with things like scarves. And kudos on sharing one suitcase for 10 days. I like to pack light, too, and a lot of my (American) friends don’t understand how I can only have a carry on for a two week trip. It’s not that hard if you don’t mind wearing things more than once.

    Meg Reply:

    HA! My mom says, “Me and packing light don’t mix”- I swear..when she comes for the weekend here (I live 1.5 hours away from her) she brings at least two suitcases, a bag for her hair products, and then any food she wants to eat (we don’t have the processed crap she likes)

  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! :(

  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. :)

    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..

    Jenna Reply:

    I think the key is volume. I never had “outfits” until I went to the thrift store and had more clothes in my closet. Most looks seems to be composed of layers, using either items of clothing or accessories. And notice how I use a belt whenever I can! For my figure especially, that seems to be really important.

    I feel like I’m figuring this out as well, you know?

    I have a Pinterest board where I try to not only pin things that I’d like to buy, but really focus on pinning outfits that can be created using pieces I already have in my closet

    Stephanie C Reply:

    Oh my gosh.. I am so with you here. I just wear t-shirts and jeans almost all the time. If I’m feeling adventurous I’ll do a cardigan with a long necklace.. but that’s the extent of me putting together an outfit.

  24. Hi Jenna,

    Thanks to share with us!

    I have a few doubts… it’s our (me and my husband) first international travel together and with my super Canon 60D.
    Although I love to take lots and lots of pictures, my husband think it’s not a good idea to take this large camera with us. He thinks will be better just taking a little one (point and shoot) and the camcorder, but I fought with that idea… the pictures will not be so good as my 60D!
    So what you think? You always travels to foreign countries and how do you do it? It’s really that bad wearing so much weight?
    Do you take your good camera or just a small one?

    Well, I’ll travel to USA in 10 days, we’ll spend 30 days on the east coast and I was thinking to buy a small camera, but a good one, like Canon S95. What you think?
    Can you give me some tips about how to take good pictures while travelling?

    Thank you!

    Jenna Reply:


    I am biased, and I say take your big camera. The pictures form a small camera won’t ever compare to what you can capture with a dSLR. It stresses my husband out, but I try to take on the responsibility of caring for it, and carry it most of the time. If you don’t want to take multiple lenses, you might want to look into renting something like a 24-70 that is very versatile but still very high quality.

    I think for a trip where you are putting a lot of time and money, it makes sense to take the camera you love and document your time there!

    Thais Reply:

    I’m with Jenna!

    I’ve taken my 7D in all international and home trips. The camera has been to Paris, Costa Rica, Boston, NY, and now Italy. TAKE IT, you will not regret it. Especially for night time shoots.

    Camila Camargo Reply:

    Thanks girls for the tips!

    I talked to my husband and I’ll bring my camera!!!

    Can’t wait!

  25. Um, can we talk for a second about you in that last picture? AMAZING. Seriously, you’ve looked stellar in so many of the pictures you’ve posted lately, but I think that this one is the best. Way to go, you! Now go out on a hot date with TH and own that hot bod! :)

  26. You dress so well for travelling- it truly is inspirational. I also always try everything on before putting it in the suitcase– glad to see that I’m not the only one!

    I love the grey cardigan with the white lacy trim!

  27. Jenna, I have to say I have read your blog on and off for several years. This is my first post. Your packing tips were spot on. I could really use them… I am forever packing heavy. My dad even use to yell, “pack light” to us when we went on trips, which made Rusty put a pair of underwear in his pocket and go. We weren’t aware of it until Sunday came and he didn’t have his church clothes. We now tease him about it. ;) Thank you for posting photos of home, I never tire of seeing pictures of the “slope.” Keep writing, I love it!

  28. This is such a great idea and I wish I’d thought of it myself! If I’m going somewhere for five days, I’ll sometimes write down “dark jeans + black V-neck sweater” for Monday, etc., etc. but the picture idea seems more fun (and anything to make packing more fun is a good idea to me). Also, I love the skinny jeans on you. I just bit the bullet and bought a pair for myself at Banana Republic and WHY have I been intimidated by them before? They have a ton of stretch to them and I feel like I’m wearing fat pants. Except they’re skinny jeans. Awesome.

    Also, I am off to google the Cole Haan flats of which you speak.

    Jenna Reply:

    Yes! Skinny jeans are so comfortable (no wonder all the skinny girls live in them) but I was always quite scared of them. I do think I’ll feel more confident in them once I lose another 20 lbs, but I’m glad I decided to take these to Europe.

    phruphru Reply:

    you look really good in them right now! really!

  29. I love your outfits! I especially love the colorful shirts you picked up in Europe and your use of belts as accessories. I’d love to try to do that more in my own wardrobe. I really love your outfit with the jeans, flats, yellow tee and brown belt…right up my alley!

  30. I am going to suggest that you try replacing that substantial black belt with a chain link belt.

    Jenna Reply:

    I always love your input (not said sarcastically in the least, btw). One like this girl on the left, without the mustache? http://pinterest.com/pin/170461234/

  31. Oh Jenna! I tried on outfits before leaving too. My problem is that I packed tooo light! I run out of bottoms and like you I’m having a hard time with the weather. It’s cold when we leave in the morning and darn hot by noon. Although I think I have much more mild weather than u did. We are in Florence right now, and I better go to sleep bc tomorrow is a super early morning. You looked amazing!

  32. I really, really like that black dress with the bright blue shirt underneath it. I also like the purple sweater, and the pinkish new shirt you bought in Italy. It looks like your system worked out perfectly.

  33. I SHOULD DO THIS More often. The only successful packing I have ever done is

    1-a 3 week trip through Asia in a carry on. Because I had to pack limited outfits.

    2- business trips, again outfits.

    I never thought about doing that on actual vacations.

    Also I love that scene in clueless!

    ? Celina =)

  34. You look great Jenna! I think those skinny jeans are very flattering on you!

    I ended up taking pictures of all my different outfits before our trip to Jamaica this summer and it completely changed my packing experience. Before, I was just like you and would usually end up feeling like I had nothing to wear.

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