Happy Monday, gang! 🙂 How was your weekend? Mine was…well, to be honest, pretty sucky. I wasn’t feeling well all weekend, but *sigh*, the week has begun so it’s time to get crackin’!
Last month, my mother & I had the good fortune to accompany my father to Toronto for an overnight trip to the Westin Harbour Castle. He had some kind of presentation to give the next morning, so that’s why we decided to stay. It was a fantastic weekend, filled with fun, laughter and good ol’ fashioned good times with my fam. I took a fair share of photos, so I’ve been filtering them through for the last couple of weeks in preparation to share them with you (look for a travel diary of sorts later today!), but first, I wanted to compose a kind of “overnight essentials” packing guide for you.
As it was only an overnight trip, I took my trusty Herschel backpack to carry my belongings. I’ll tell you, this backpack was a whopping $90 (because of its huge size, methinks), but it has shown its worth time and time again. This backpack comes with a handy laptop sleeves and extra pockets so it was the clear choice for me to take along with me to get everything in that I wanted.
For my more delicate items, like my toiletries & makeup, I used a pretty Forever 21 makeup bag & my “Pretty” Elizabeth Arden bag (which was a gift with purchase that my mom didn’t need so she gave to me years ago, and it’s been a delight!).

Sometimes hotels are cold and/or you can’t bear the thought of sticking bare legs under their sheets, so I usually bring both pants and shorts to wear to sleep and decide when I’m there. Seeing as it was the middle of February in Canada, I opted for the pants. 🙂
As well as catering to your trip’s needs (which I’ll get to in a minute), remember to pack pajamas and/or a comfy outfit to change into! Yes, it might be difficult to stuff into the bag you’re taking and yes, your travel partners might look at you like you’re a bit ridiculous, but I can’t tell you how many times we’ve gone on vacations as a family and I, the resident overpacker, has exactly everything she needs, and my mom, the resident underpacker, needs to find a store to buy new things. I partially think that it’s a plan that she has going on, and one that is a winner, because she always comes back from trips with both souvenirs and nice, new clothes, but that’s fair enough. I’d personally rather plan everything out and have exactly what I need rather than be panicking at Target in Philadelphia 5 minutes before close trying to find pajamas to wear for the night (true story)…just sayin’.
In this case, in terms of trip specific clothes, I wore leggings and a hoodie down to TO (always remember a hoodie, hotels are sometimes FREEZING, and it sure is nice to be all snuggled and warm when you know that you could be shivering), but I knew we’d be going out to dinner, so I bought a nicer blouse to change into on arrival. I ended up wearing my comfy set of clothes (the thermal top & leggings pictured above) on the way home because it just happened to be snowing like crazy the next day and I couldn’t be bothered to wear my nicer, more formal outfit in the bad weather.
Next, comes entertainment, my second favourite part! We’ve done a couple of trips like this in the past, so I knew that we’d be spending the night in an über swanky hotel, but it’s still nice to have backups in case your mom hogs the TV or something… 😉
I literally can’t go anywhere these days without taking my Lily Pulitzer agenda. It’s a wonderful option for all my organized gals out there (or the ones who are faking it until they make it, like me). Whenever I have an idea for a post or think of a new angle to approach an essay, I write it down in my trusty gold-foiled notebook, which you have probably seen multiple times on my instagram (favourite notebook ever). I also brought my Beats by Dre headphones in case I felt like being anti-social (LOL, let’s face it, Beats are awesome, but they’re also so alienating) & my e-reader to enjoy any of my current reads as I snuggled into bed.
For the main event, the toiletries & makeup, I decided to share my tips via image so that you can post it to Pinterest or Tumblr and be able to access them easier than coming back to this post any and every time you might need it. First up, toiletries!
Now, obviously, these are just suggestions based on what I’ve noticed I need, but please feel free to add or remove any items according to your individual needs! I also think it’s important to share that a lot of these items I had samples of, which is perfect for one or two uses, so if you can, stock up on those prior to an overnight trip (it saves you having to use those annoying and sometimes messy travel jars). Oh, and I don’t wash my hair everyday, because it can actually strip your hair’s natural oils and lead to serious damage, so I didn’t include shampoo or conditioner on this list. However, if you feel icky without some kind of hair cleansing, dry shampoo is your best friend (and it will give you lots of volume!). Finally, in the “other” section, I listed makeup wipes, but if you get as annoyed as me at the thought of carrying a whole package or even a travel package of wipes, just use my simple trick: put a single makeup wipe in a small ziploc bag, like the ones you recieve samples in from Sephora! It saves you both space in your toiletries bag and the threat of losing your entire package of (usually expensive) wipes in a hotel bathroom on an overnight trip. 🙂

Alright, it’s official: I LOVE the Beauty Blender, and I use it wet more often than I do dry now. That’s what I call progress, friends!

Items marked with a * aren’t exactly makeup items but are small enough to fit in a makeup bag and are essentials for pulling everything together.
I know that the above list seems like it would be a lot of makeup, but it’s really not; I can fly through application for all of these products and be done my whole face within 8-10 minutes if I want to! This is just a general guide, you might have to add an item here or there to work for you. However, I think I got most of the items that are needed, including a more dramatic lip colour for the evening if you are going out. In fact, to be honest, I only wear a few of these items on an average day, but I brought them all along in case I wanted to switch things up for dinner on our first night or wanted to go crazy the next morning. Furthermore, some of these items are the simple, less complicated options in that category of makeup, for travel’s sake. For instance, the eyebrow pencil; while you may not use a pencil to fill in your eyes everyday, pencils are generally much easier and quicker to use and don’t require the extra brush that you’d need to, say, use a cream or gel product. Plus, you can always sharpen the pencil before you leave home! The same rules apply to eyeshadow; I don’t know if it’s just me but the last thing I want to do when I’m in a hotel is sit and fuss with lid and crease shadows. Instead, I usually opt for a cream-to-powder eyeshadow that I can apply with my fingers but will still give the impression that I spent loads of time on my eyes. Plus, these shadows usually last longer on the eyes so they work in any environment or temperature. Now, that’s what we call a makeup fakeup! 😉
As you can see, this is the completed look. Nothing fancy or super eye-catching, just your average makeup but it only took a few minutes to put together and didn’t take a bevy of products to do so! Win, win! 🙂
Well, there it is, the essentials that I think you and everyone could make use of during an overnight trip. I don’t feel like it’s much, and these are things that I use everyday at home, so it was really a no-brainer to include them in my “to bring” pile. However, if you think some of it is a bit “overkill,” as aforementioned, modify it to suit your own needs! These lists and ideas are merely suggestions, and in my opinion, one of the best parts of any trip is packing, so you need to both customize what you bring to YOU & your needs for your trip all while having some fun with it; you’re going on an adventure, for crying out loud! 😀
Thank you so much for reading my first ever guide to packing, and be sure to let me know if you want to see others for different kinds of trips!
What are your go-to products and items to bring along with you on overnight trips? Did I miss anything that you simply cannot live without? Are you an overpacker or an underpacker? I’d love to know!
Much love,
S♥