Alternatively titled, “How I wore only dresses from thredUP and packed in just a backpack” πŸ˜‰
I had so much fun figuring out if I could pull this off– and I did! Simple, effortless, fuss-free, minimal packing and dressing is my desire and ambition. The more I put these adjectives into practice, the easier it becomes to achieve them. πŸ˜‰ 
// my bags// 
My trusty pleather backpack ($25 at Ross) that transported all my outfits and my “new” bag ($3? at a charity shop) that carried my toiletries, day planner, book, and two pair of flip flops along with my usual purse items.

// Thursday at Teach Them Diligently + traveling //
Just because our family always finds the most complicated way to do things, on our way to Florida we stopped in Nashville Thursday afternoon and evening to attend the Teach Them Diligently homeschool convention. It was lovely and a great time with friends we don’t get to see very often, like Blimey Cow! I also met a few readers which was fun. πŸ™‚ I wore my favorite En Focus Studio dress with leggings and comfortable Sperry’s. Easy for the conference and great for traveling through the night. 
// Friday morning + afternoon at New Smyrna Beach //
We drove from Nashville straight to sandy shores. Thankfully we found a bathroom to freshen up in and change into beach clothes. I knew I wasn’t going to be swimming (too cold!) so I didn’t bring my swimsuit. Instead, I threw on this awesome Champion brand dress and a Halftee

We only stayed at the beach until lunch time then we headed to our hotel to unload and play tennis in the sun. This was the perfect outfit for that and for watching my siblings as they played in the pool. 

// Friday evening dinner on the patio //
After a hot day, I showered and changed into this Converse One-Star dress for the evening. We ate our supper on the patio in the perfect weather. This dress has a peep-hole style neckline that needed filled, but instead of wearing a tank (which would have added bulk around my hips) I wore a Cami Secret(flipped so the lace doesn’t show) that made this easy peasy lemon squeezy. Plus, no tank saved room in my suitcase.
// Saturday morning breakfast + tennis //
Since the wedding wasn’t until 3 in the afternoon, I made sure to take a dress for the morning so I wouldn’t hang out in my pajamas or my nice dress until it was time to get ready. Our whole family played in the sun together which was enjoyable and I got even more red (isn’t that what you’re supposed to do in Florida?) This is another from the Converse One-Star brand. I wore it with a navy blue Forever 21 tank underneath and a long gold necklace. The earrings you can see are the ones I wore Thursday and Friday also. I like them because they’re big and cute and easy to find if they fall off in the car. 

// Saturday afternoon wedding //
We had the privilege to attend the covenanting together of two good friends and afterwards party in celebration of what God has done in bringing them together! This The Limited dress turned out to be super comfortable for dancing (eeeeeey macarena!) and I loved wearing sparkly jewelry and my favorite silver heels. A Halftee made it modest with ease. 
(Yes, I wear headcoverings to weddings, too! They are public services of worship. :))
After the reception, a bunch of us went go-karting. I had never done that and boy, was it awesome! I always throw a pair of jeans and tunic into my travel bag whether I expect to need them or not, and I’m glad I did so I didn’t have to worry about my skirts flying up. πŸ™‚ 

// Sunday morning church + Publix run //
Bright and early Sunday morning, we attended church at St. Andrew’s Chapel in Sanford, Florida. Dr. RC Sproul was preaching and it was incredible to hear him in such a pretty building. I borrowed my shoes and headcovering from the day before and threw on this Express black eyelet dress and my favorite Rue 21 Cardigan. I put back on my big earrings and wrapped Saturday morning’s long gold necklace around my wrist for a bracelet. This dress was a little low, so I once again fixed that with a Cami Secret.
// Sunday afternoon + travel home //

Maxi dresses are the easiest thing to travel in, I’m convinced. I wore this Green Gate dress with an Old Navy shrug and it was comfortable and fuss-free. I left my jewelry on from church that morning and slipped on flip flops when I needed to get out of the car. πŸ˜‰

Tips and tricks for easy, concise packing:

  • Eliminate layers. I only took one tank top on the trip and chose dresses that didn’t need a bunch of layers to make them modest. Halftees are easy, take up little space, and are cool for Florida weather. 
  • Roooooll those dresses. I was a little reluctant to roll my nice dress up and shove it in my suitcase, but I checked the care instructions and it could be ironed, so my mind was set at ease. 
  • Think about exactly what you’ll be doing, and pack just for that. I had a general idea of what we would be doing each day and didn’t take anything extra “just in case” like I usually do, with the exception of jeans+a tunic. This allowed my bag to be small and I didn’t have to decide between outfits. I just wore what I had and felt collected and confident instead of flustered or unsure of my decision. 
  • Plan your jewelry as you’re packing. That way you don’t have to waste time rummaging through your case and like the previous point, you can be confident of your choice. The jewelry I wore is the jewelry I took, with the exception of one necklace I planned on wearing but didn’t because I realized it’d give me a tan line. πŸ˜› 
  • Be smart and take what you need. I was tempted to wear flip-flops to the homeschool convention so I wouldn’t have to drag the Sperry’s around with me through the weekend when I didn’t think I’d need them again, but decided to do my feet a favor and wear them. I ended up wearing them to go-karting Saturday night and was oh-so-glad I had been smart about comfortable footwear. πŸ˜‰
  • Be thinking about your wardrobe ahead of time. I kind of had this trip in the back of my mind for a couple weeks and kept an eye out on thredUP for the filler pieces I needed, like that gray cardigan (which was only $3.49, BTW). 
I hope y’all have an awesome weekend, as well! What are your weekend packing tips? Did you attend Teach Them Diligently

53 thoughts on “How I Packed | A Weekend in Florida”

  1. Hey there. I'm curious on your thoughts on head coverings. I've gone back and forth with that and even though I didn't wear a headcovering or anything our family went to a conservative Mennonite church. But my question is cause this is the one that would get me. Why would you wear a headcovering only in church services. God says to pray without ceasing and we should be worshipping Him always so why wouldn't you wear it all the time? Those are just the questions that were brought up when I was looking into it and I would love to hear your thoughts on it.

    1. I've herd that women should cover thier heads but that your hair is your head covering. So if your bald you should wear one

  2. I loved this post, Olivia! My favorite outfits were the first and the last. My family is going to FL in April, so I'm definitely going to have to use some of your packing tips. Thanks! πŸ™‚

  3. I love how you can fit everything in just two bags. If you don't have any dresses, you can roll up skirts too. Just make sure you can iron them if need be. I love your outfits Olivia!

  4. Hi. My name is Channa. Im Jewish and from the UK. I follow the jewish laws on modesty which means no mens clothing and covering from the collar bones to about 4 inches below the knee and to the same length below the elbow.
    I also cover my hair in accordance to the tradition im from.
    I really love how you dress modestly without looking obviously religious – you can spot me as religious a mile away!
    One thing Ive really learned about clothes – especially when Im travelling is to buy things that multi task. So a tunic top that is long enough to be worn over jeans can also double as a top tucked into a skirt. Also dresses can be worn over skirts for a more flowey layered look. Cardigans can double as tops if they are a tighter fit and button down shirts can double as cardigans / cover ups if you don't button them up. I find this really helps – especially as I often have to go from one situation to another (ie Synagogue to my parents house) where different clothing is needed .. A dress tucked into a shirt only needs a pair of jeans and I have a completely different look without having to bring a whole new outfit.

    Anyway – I think some of your ideas are great and I love how I can take inspiration from them even though we aren't the same faith !!

  5. Cute! But, I think they are a little short, your are showing your knee in almost all of them. I thought you tried to wear skirts/dresses that are below your knee?

    1. Thanks! They all hit the middle of my knee standing, and cover my knees when sitting, which meets my standards, although obviously if they were longer I'd prefer that. I don't understand why bending my leg makes it look like it's shorter than my knees in the pictures, but it does. :-/

  6. The weekend at Teach Them Diligently was great. There were a lot of awesome speakers. I was there on Friday and Saturday so I missed you! πŸ™ Maybe next year?


  7. SO CUTE!!! Loved all your outfits. A few years ago my family (of 13) traveled east for a wedding. Packing that many people that distance was something. And we did not have the space to pack a lot of things. I wore flip flops most the time so I could kick them off while we were in the van. I hate wearing shoes in the car.

  8. Olivia, you asked about packing tips, so here's my vacation wisdom. My family and I (there are six of us, including me) drove all the way to Prince Edward Island and back this summer. We had to pack enough for six people for three weeks, including swimwear, beach towels, and sleeping bags and pillows. As I'm sure you can imagine, it was…interesting. Reminiscent of two summers ago, when I had to pack two-weeks worth of clothing in an airport-regulation suitcase all the way to Paris and back. Also interesting.
    As a result of these packing adventures, I have one top packing tip: never assume something will be provided, but don't get carried away. I brought an extra jacket on my overseas trip, which ended up being good because my friend didn't bring one and it was cold and rainy some of the time. I was a life-saver because I had extra conditioner. I always recommend rolling, and it helps make room for those possibly-life-saving extras.
    I also highly recommend bringing a small bottle of laundry detergent. That way, you can wash an article of clothing if you get something on it and don't have to change your shirt or whatever.

  9. These are cute outfits! I really like the one you wore to the wedding… you are able to pull off wearing a "traditional" looking head covering, without it looking frumpy, so well!

  10. This is one of your best posts! This was really helpful as I tend to always over pack. πŸ™‚ I love the way you wear your head covering. Where did you get it? I wear head coverings, too.

  11. Just checked out thredUP for the first time after linking from this post. Ordered 5 dresses!!! Can't wait to see them in person and tailor them to fit me! Not sure why I haven't checked it out before, but so glad that I did today!!!

  12. Wonderful tips and adorable outfits! Oh my goodness! What an amazing way to be modest even if you are in a hot location with a beach and everything else that might tempt you to be "less modest". You are definitely an inspiration, Olivia! I loved it! =)

  13. Hi Olivia ! I totally understand about you wearing a headcovering to wedding services ! I wear a headcovering whenever I'm praying with other christians (except for the family ;-)) since last summer, after doing a camp with a young lady from a family as conservative as mine and having good discussions with her. Before that, I was only wearing it for church's meetings (sunday service, Bible study and prayer meeting). It's nice to see you persevering in this conviction !
    I really like the sunday morning look and the maxi dress… Soooo cute! The other dress are a bit too short for my taste (you probably should wear something underneath to make it longer, don't you think?!) but the pattern are cute. I personnaly own so little dresses that I could count them on one hand πŸ˜‰ And it's basically the dresses I made myself to be my sister and brother's bridesmaid πŸ˜‰
    I haven't had to do a lot of packing recently. I went to the east of France (Strasbourg) for a weekend in february, and I wore a denim skirt to travel on friday night and to spend time with friends on saturday, and 2 different tops and cardis. On sunday, I wore a shirt, another skirt and also a different. I guess it's not the most efficient way of packing because I didn't minimize the clothes I took, but it was nice anyways πŸ˜‰
    Have a great week and thanks for sharing all those outfits !

  14. Wow, you had a busy weekend! It sounds like so much fun, and I loved seeing all of your outfits. They seem really well-planned, practical, and of course cute. πŸ˜‰ My favorites were the ones you wore on Thursday and Friday. Great tips, too.

  15. Very cool post, Olivia! I love to travel; I wish I could go to Florida. ;p When I travel, I can make due with a carry-on suitcase of clothes for any amount of time. I also love your head coverings! Do you make them yourself? How long do you like them to be?
    God Bless,

  16. Oh, oh, you make my feet itch to travel and my fingers ache to find some more pretty dress to add to my small collection!
    Love how you styled each dress, and my favourite dresses from this post are: the Converse One Star dresses, your wedding outfit and the Sunday afternoon maxi with the grey shrug. Keep it up! I'm going to go make some Cami Secrets, now. πŸ™‚

  17. Your outward, as well as inward beauty is much more beautiful and wholesome than Taylor Swift. :p

    Miss ya girl and looking forward to seeing you this weekend!

  18. Love this! I am planning on doing a similar outfit series when I travel to the US in May for 2.5 months. πŸ™‚ And I really want to get something from thred up….. just can't seem to find something I love to use my credits on.

    1. (Sorry for answering this and commenting twice…Hope you don't mind, Olivia!) So Thredup is kind of like an online consignment shop. The "shop" buys semi-worn or new clothes from people and sells them at a much cheaper price. It will often have more pricey brand names or store clothing but it will be from 70-90% off! Really great site, you should try it out! =)

  19. I love this article, Olivia! πŸ™‚ I always tend to overpack, so this kind of thing encourages me to think smartly about what I'm going to bring. πŸ™‚
    Thredup looks like it has some gorgeous stuff! πŸ™‚ I especially love the maxi dress. πŸ™‚

  20. Hey Olivia! I'm thinking about ordering a half tee to try out, and I wondered if you could answer a few questions about them for me. I don't want to get one if it's not what I want. πŸ™‚

    1. How many fingers below the collarbone does the higher side sit?
    2. Do they ever slide up and bunch?
    3. Are they actually comfortable?
    4. What size are you? (You look about my size, and the size chooser thingy said Small for me, but just wondering. ;))

    Thanks Olivia! (Or anyone else who has a half tee and can answer. :D)

    1. Hey!
      1) I don't usually wear it on the higher side, but I would guess it's about 1" below my collar.
      2) Never!
      3) Extremely comfortable. Sometimes when I'm wearing the smaller size for 16+ hours my shoulders get a little tired, but no worse than any other shirt.
      4) I have a small and a medium, and they both fit. The small is lower, but I like how the sleeves are tighter. The medium is more comfortable.

      Halftee emailed me last night with a coupon code for my readers! Entering "freshmodesty" at checkout will get you 25% off. πŸ™‚ Hope that helps!

    2. Thanks so much, Olivia! I think I'd really like to get at least one to try, because it would make finding clothes so much easier; it's so hard to find things that aren't revealing, especially here in NZ. Now my only problem could be Half Tee telling me they won't ship here. :/

      By the way, thanks so much for the coupon code! Is the 25% off for each product, or each shipment? Thanks again!

  21. I would wear all of these… Congrats on finding a maxi dress that fit!!! Short girls have the worst time with those;)

    Love how you did it all in dresses! and your bangs look amazing in the pic with your hair in a ponytail and your cute earrings!!

    Cool about getting to hear RC Sproul;) hope you had a great time!

    I NEED some half tees! Oh, and the silver heels you're wearing… Prob the best ever!

    Abigail of

  22. Travel packing posts are the best! I love your last two outfits the best. The pink cardigan withe black dress is so gorgeous, but then the beautiful soft colours of the maxi dress withe grey bolero suit you so much πŸ™‚

    Your packing tips are definitely ones I travel by.

    ~Esther of Oz

Leave a Reply

Your email address will not be published.