How to Pack Outfits for 2 Weeks in Italy

Packing Outfits for 2 Weeks in Italy: Style Edit

Packing outfits

2 weeks in Italy? No problem.

Packing for two weeks away is no small feat. Remaining light enough to be mobile while still having all the items you need can both be quite an accomplishment and a daunting task. I spent weeks before my Italy adventure thinking through my wardrobe and picturing capsule outfits that would play well together and be the perfect visual complement to wear in the land of linen and summer-drenched beauty.

In today’s post, we’ll explore tips I’ve learned on how to pack for a 2 week Italy trip, my visioning process, creating a capsule wardrobe, suitcase versus carry-on, and the key items I brought to complete my Italian capsule wardrobe.

Let’s go ahead and jump into it.

Part 1: Planning

Packing tips for a long trip

Suitcase or carry-on?

It’s the age-old question, and one you absolutely must ask yourself FIRST before you start thinking through what to bring. If you can manage it, aim for a carry-on instead of a suitcase, and bring a larger personal item (backpack, etc.) with you. It makes things so much easier when you’re constantly switching flights and flitting about from one terminal to the next. Expediency is key when you’ve got a 1-hour layover and flights are delayed or off schedule.

I fit quite the wardrobe into 1 carry-on and 1 large backpack. You may need more or fewer items depending on how long you are away, but I packed, in general, enough to have a cute/casual day look, plus an option for evening, on most days I was away with the opportunity to mix and match tops, shorts, and pants (capsule wardrobe style). 

Timing matters

As a general rule of thumb, it’s best to start early. Earlier than you think you need to. For a two-week trip like this one where we planned to tour the Amalfi Coast and Rome, I start envisioning months before, and I start pulling aside clothes 2-3 weeks before departure. It may feel silly to start trying on clothes and putting them aside a few weeks early, but it always pays to be prepared, and you’ll avoid the inevitable “bad packing decisions” that ensue when you feel pressed for time, or you work on packing when you are under the gun and no longer excited about it.

Try everything on

It’s important to try on EVERY piece to make sure you like it and it fits the occasion. We all know the feeling of trying on something that you thought would be absolute perfection and then it’s just… not. It’s not suitable for the place or it doesn’t quite fit the occasion. You can just feel it. 

My best packing tip: the secret to “effortless” travel outfits

Take pictures of your outfits and add them to your “notes” app

Here’s a life hack that I created after one too many trips where I opened up my suitcase and suddenly could not remember what I’d packed or planned to wear. I’ve found this hack to be massively helpful, keeping me on track with minimal effort. Add photos of each outfit (preferably a mirror pic of you wearing it, accessories, and all!) to a trip note on your phone and watch morning styling become a breeze. The best time to snag those photos? When you are trying the outfits on before packing. And yes, this is worth repeating, you must try them all on. This is non-negotiable.

Tips to organize your notes

To expand on this, I have found it helpful to name the note something easily searchable within the notes app, like “Italy trip.” Then, my corresponding headers will be the different places we are staying (i.e. Ravello, Positano, etc.). Then I go another layer deeper. I create subheaders under each town/city with the category/occasion: casual/day dresses, other casual outfits, hiking, and evening wear. So if I know I want to wear my green silk dress with Tory Burch flip flops, black purse, and gold jewelry at Ravello when we visit their famous gardens, I open my notes app, search for Ravello, look for day dresses, and am able to quickly find the photo of the outfit and accessories to match. Easy!

Your time and energy are valuable

Why is this important? Your time in a different country is precious. You don’t need to be wasting your valuable time and attention in the morning wondering “Wait, what was I planning to wear”, and sorting through all your clothes, trying on, taking off, only to remember that you were mentally saving that outfit for another day. It can be quite exhausting and is a totally unnecessary quandary with the right planning. You do not need to go into each travel morning like this.

Spend time with your decisions

You may be thinking, “Well yes, I get the idea, but you’re spending time, effort, and energy 2-3 weeks ahead of time on planning it, which seems like a lot… does it really matter if you envision, choose outfits, and pack 3-4 days before as opposed to 2-3 weeks before?” My answer would be: “It definitely does.” The benefit of starting 2-3 weeks in advance gives you time to sit with your choices. Personally, I need time to sit with decisions and listen to my gut to check if something feels right. For example, you may make a decision to take a particular dress, and then after reflecting for a few days, you realize that actually, it would be more suited if you wore instead this other dress that better fits the occasion, or is more comfortable, or just simply feels right. It’s important to note that it’s actually part of the planning process to go through stages of reflection, analysis, and changes to plan. This is normal and you should give yourself time and grace to do so without rushing on your part.

Don’t believe me on the power of the no-rush, pre-plan?

Here’s an ideal scenario:

Imagine, you, waking up in a beautiful country with the soft morning sun peeking lightly from a nearby window. You leisurely stretch, unwind your rested limbs and walk to the window to look outside. You realize that today is Saturday, you’re in Positano and you already know what you’re going to wear (at least you know the packing “you” knew). You open up your notes app and bring up the photo you snapped of you happy and confident wearing the beautiful outfit you selected for today. Your eyes catch on the jewelry you’re wearing in the photo. You remember exactly where everything is packed, and so, checking “What am I going to wear?” off your mental list, you promptly turn your attention to more important matters: “Now where can I get coffee?”.

Isn’t that a much lovelier experience?

Part 2: Packing

What I packed for Italy: a capsule wardrobe list

As you can see from some of the product photos of my favorite items that I packed, I kept my color scheme pretty simple. I chose white, black, and occasionally a light blue, with sage green as my emphasis color. Keeping it classic and sticking to colors that are easy to mix and match makes it a breeze to combine different combinations in a way that allows getting dressed each morning to feel delightful. However, sticking to classics to create your capsule wardrobe doesn’t mean you can’t have fun! You absolutely must make room for statement pieces - whether that’s wardrobe attire, a scarf, or jewelry that you know will add to your look, and make you feel incredible when you wear it.

My outfit packing list for two weeks in Italy

Dresses

• 10 - 12 dresses (materials are a mix between silk, cotton, linen long, linen, with a variety of lengths to fit casual/day and evening/elegant attire).

Shorts and Pants

• 1 black and 1 white linen (casual) day shorts

• 1 pair of linen-blend (nice) white shorts

• 2 pairs of linen white high-waisted pants

• 1 black and 1 sage green flowy linen-blend (versatile) pants

Tops

• Linen crop tops to mix with pants and shorts (1 white, 1 chambray, 1 black, 1 white with flowers).

• 3 bodysuits: 1 white, 1 black, 1 blue

• Activewear for a hike/casual/airport: 1-2 activewear top options, 2 light activewear jackets: 1 neutral/nude colored and 1 black

• 1 nice (light) jacket in case of chilly evenings

Shoes

• Tory Burch sandals (used as my basic sandal for most of my day/evening dresses)

• Roman-style sandals (a casual/cute option that went well paired with a long grey linen dress while visiting Pompeii).

• Gold square-toed small heels (small heel, worked well with evening wear and our engagement pictures).

• Black and white ON tennis shoes (for hiking)

Accessories

• Gold jewelry (I mainly stick to gold, as opposed to silver due to my skin tone. Also, gold jewelry is very warm in color, and goes well with summer attire).

• Sunglasses (at least 2 pairs: 1 classic black, 1 aviator style)

• White floppy hat with black band (I only used it for daytime with a light or casual summer dress, nice top, and flowy pants, or take it with you for a beach day).

• 1 small black top-handle, crossbody bag (I wore this with everything. If you can only take one bag due to space, I recommend a neutral color).

  • If I had my way, I would have also brought two others: the white/rattan and sage green crossbody options I showed above, but alas, the packing gods had other plans for me.

How to pick the perfect wardrobe from your own closet

My attire goal for Italy was simple. I wanted to look nice, be comfortable, and most importantly, fit the environment and occasion. The easiest way to do that was with dresses since they are 1 piece of clothing instead of a few. And when do dresses not instantly elevate a look? But if dresses aren’t your thing, you can easily make a capsule wardrobe with the same amount of nice tops, and cycle between pants/skirts/shorts instead.

Prepare your vision

Just make sure to plan in advance so you don’t overpack! I suggest writing it out in your notes app so you can clearly see: 5-6 evening dresses, 5-6 day dresses, etc. Get into it! You’ll be surprised by how much it helps you when you’re traveling, and you can just pull up your notes app and scroll through outfit choices to pick from without even touching your suitcase yet! Plus, you’ll look put together because you planned for it.

Start first with the items that thrill you

Once you’ve identified your goal and vision for the trip, it’s time for selection. Fashion, and most of all, style should first and foremost be FUN. It should never feel like you are utterly uninspired by what you choose to decorate your body with. There’s a certain joy in putting on the perfect pair of linen pants and finding the oh-so-perfect crop that delicately complements your figure. Find pieces that make you LOVE the way you feel in them, and feel like a representation of who you are NOW. Try on every piece and visualize yourself walking down the streets wearing that dress. Do you feel utterly fabulous? Great, pack the dress/set it aside, because it’s coming with you. But don’t forget to snap a quick photo of your getup for your notes.

This is a GREAT time to play around with statement pieces. A lot of times what can start out as a “plain” or “ordinary” capsule wardrobe outfit just needs the right statement piece.

CLothes of a feather Pack together

Speaking of your notes app, remember that helpful hack I mentioned earlier about taking pictures of your outfits and categorizing them by the place you are going (name of note) and occasion/category (subheaders)?

Well, that’s going to come in handy now, because once you’ve taken your photos and organized your notes app, it’s time to pack!

Invest in packing organizers to separate out your clothing categories:

• For example, pack all casual/day wear in an organizer specifically for JUST your casual/day wear. That way when it’s morning in Ravello, Italy and you’re looking through your notes app for your casual/day wear, you can grab JUST that bag, and perhaps your accessories carrier from within your carry-on without rummaging through everything.

This helps ensure everything stays nice and tidy (including your mind).

Consider the weather

For example, on most days during the end of May/early June, the weather was forecast to be sunny with a slight chill in the evenings. I didn’t particularly want to wear long sleeves on my summer vacation, so I opted to bring a light, nice jacket for those evenings to grab for dinner, OR to cover my shoulders in the Roman churches. 

Fill in the blanks

Once you’ve identified the pieces you absolutely cannot wait to wear, the next step is to put on your practical lens and identify the areas you might not have covered. 

Stop, drop, and ask yourself: a checklist

• Am I taking this in too many colors? Can I condense it to one or two of my absolute favorites?

• What am I missing? Have I thought through the occasions and excursions, and do I have a clear picture of what I could wear for each? Visualization is key.

• What am I usually guilty of forgetting? Can I set that aside now so I don’t forget?

• Do I need three purses? Ok, you got me… this last reminder is just for me. I’m still a bit miffed that I couldn’t take all three of the purses I set aside to bring. When in doubt and short on room, bring the purse that goes with most outfits, and can be worn at different times of day, i.e., a small black or tan one would work nicely. Ask yourself, “What purse can I bring that I can take from day to night, effortlessly?”

Those are my top tips for packing and details on how I packed for a 2-week trip to Italy.

See you next time!