Vacation Outfit Ideas; Day to Night

Good morning! As we discussed in my Carry On post, I’m a weeeee bit of an over packer. I tried my best to downsize for our trip to Italy by planning out most of my outfits beforehand so I could narrow down the essentials. I have a tendency to pack numerous pairs of jeans (you know…options) which is ridiculous because what always ends up happening is that I wear the same one pair over and over. I wanted to bring pieces that could multi task or be worn both day and night, but I also did not want my outfits to seem repetitive. Since I have an inexplicable, stupid obsession with taking selfies in the mirror I decided to turn them into this somewhat cohesive (I hope..) post.

First, let’s list the essentials:

  • 1 pair of black leggings
  • 1 pair jeans
  • 1 pair pants [dress slacks/cargo pants/etc. I went with skinny cargos]
  • a basic tank
  • booties
  • strappy heels
  • scarf
  • 2-3 versatile dress tops [ie, one that could be worn day or night]
  • leather jacket
  • sweater
  • t-shirt

So, here’s how I styled (or tried to) these pieces for day and night along with a quick recap of what I wore them to.

Day 1: Travel & Dinner


On the plane ride from NY to Italy I wore a basic tank, leggings and denim jacket (seen here). We took an overnight flight and arrived at our hotel in the morning. All I wanted to do was freshen up from the flight and change into clean clothes, but our luggage hadn’t arrived yet so I threw on the t-shirt I’d packed in my carry on. It did the trick and I wore it for the day which was spent wandering around the hotel, area surrounding it and taking an accidental several hour nap before dinner. Both the leggings and T are from Forever 21.

After we awoke from our nap we showered and got ready for a lovely seafood dinner at a restaurant in Rome called Chinappi which was divine. For dinner I wore this green long sleeve, deep v-neck top from Forever 21 [similar one here] paired with skinny jeans from Hollister and over the knee boots from Sam Edelman [similar ones here] .

Day 2: Touring Rome & Dinner by the Spanish Steps


For our first day of touring I wanted to put a little bit of effort into my outfit since Italy is known for being quite fashionable. I paired the same Hollister skinnies from the previous night’s dinner with a basic, flowy black tank that I knotted at the waist to add a little fitted structure. I cuffed the jeans at the bottom to pair them with chunky heeled leopard booties. I topped it off with a black leader jacket from Swell, a pendant necklace and hoop earrings. This was a super comfy outfit and I saw so many people wearing leather jackets of all different shades and styles which made me feel like it was a smart, chic choice.

We loved the main area of Rome from the Piazza Navona to the Spanish Steps. As we walked around during the day we noticed a bunch of cute restaurants down the side streets surrounding the Spanish Steps. For dinner we just took a cab to that area and wandered around until we spotted a place that looked good. I wore this breezy maxi dress from Swell that I topped with a black scarf from Zara to keep warm and a bit more covered. I wore it with Sanuk sandals.


Left was my nighttime hair, which I was quite proud of! I did a small braid from a piece of hair behind each ear and wrapped them towards the opposite side to create a headband look. I secured the braids behind my ears with bobby pins. To the right was my daytime accessories. The first day was the only day I wore this much jewelry to walk around as I didn’t want to make myself look like too much of a target. The rest of the trip I kept my accessories quite minimal.

Day 3: Day Trip to Florence & Dinner with Friends in Rome


I realized that while walking around during the day, simple is best. Since we were taking a train and exploring a city quite far from our hotel I wanted to be as comfortable as possible. My go to for comfort? Leggings and a T! These are the same leggings I wore on the plane (gross, I know, but whatevs..) paired with a simple grey top that I believe is from TJ Maxx. I wore the same pendant necklace which is a cheapy little thing from Forever 21 that wouldn’t ruin my life if it was stolen. I did wear heels to Florence but heels don’t really bother me. What you need to understand is that my feet are pretty much two giant callouses, they could withstand just about anything. I wore the same leather jacket again because I love it and it looked different enough with this new outfit and still super cute.

My dinner outfit was one of my favorites of this trip. I knew I wanted to wear this black top more than once and I usually wear it with nothing under it (as I did here) so I paired it with a white bandeau, which actually completely transformed it. Also, we were joining a group of Dan’s friends for dinner so I wanted to try and tone down the girls as much as possible. I paired it with these skinny cargo pants because this olive green color and I are having a moment. I topped it off with a statement belt and these nude sandals from Zara.


Day 4: Vatican Tour & Dinner in Borghese Gardens


The Vatican was the only site that we took the standard tour route to because we wanted to learn as much as we could about all the different aspects of it. As rushed and crazy as it was, it was incredibly educational and I appreciated that. The tour didn’t leave until 1pm so we decided to sleep in and enjoy a lazy morning and leisure breakfast at the hotel. I threw on my good ol’ leggings (I also wore them to the gym in the mornings so yea…), flip flops and a long sleeve t. The T is from Marshall’s and the flips are Old Navy. Totally basic but perfectly comfy for a buffet of eggs, an assortment of breads, meats and cheeses, yogurt, cereal, veggies and fresh fruits. In hindsight I wish I ate more of that breakfast because we ate at 10am and didn’t get a chance to eat again until well after 5pm. The hanger was REAL, let me tell you.

I read that you’re supposed to dress conservative to the Vatican since you are walking through two sacred churches so I wore a loose sweater from H&M that covered everything, a thick black scarf from Zara (for extra coverage assurance) and black ankle booties from Steve Madden. It was pouring rain this day and this loose, comfy outfit turned out to be quite perfect.

It was still raining later that night and we were pretty exhausted from the tour so we wanted to stay close to the hotel for dinner. Our hotel was in the Borghese Garden area and we took a cab to a restaurant that would have been a doable 15 minute walk but…rain. It was a seafood restaurant called Galloura and it was out of this world! We ordered quite a selection and enjoyed every last bit. Even the bread here was mouth watering. Actually, all the bread in Italy was insane. I wanted to look dressed up but feel comfortable so I wore leather leggings, my Sam Edelman boots again and this Vintage Havana flowy top. My clutch is from LF. Both necklaces (day and night outfits) are from Swell.

Day 5: Wandering Ludovisi & Borghese Gardens; Dinner at Harry’s Bar


Ahh, this was a FUN day. We woke up early, downed a quick, light breakfast and headed back to the Roma Termini train station. From there we took a 10am speed train to Naples. After an hour and 10 minutes on the train we walked out to one of the worst most dangerous train stations in Italy! We were really sad to see how depressed the area of Naples by the station was. We wished we knew someone who lived there who could have picked us up and taken us to some of the good places. This reminded me a lot of New York. There are really beautiful, wonderful places and really, really depressed, awful places. So, yes this area of Naples was bad but I’m not basing my whole opinion off of the tiny little area I saw for no more than 20 minutes…it was more just us being unprepared travelers. Anyway, we got off the train, walked around for 15 minutes or so, walked right back into the train station and got right back on another speed train back to Rome. I will say though, the speed trains there are so nice that neither of us minded spending the whole morning on them! The view of the country side from the train is absolutely breathtaking and the trains themselves are incredibly comfortable and even have an espresso bar and snack area. Dan read some Italian magazines and I alternated between reading my novel and trying to take pictures of the country side. When we got back to Rome we went back to the area we’d had dinner at the night before and just explored.

My biggest mistake this day was wearing flip flops. Can I tell you that everyone and their mother gave me the death stare. People actually slowed down their cars to lean out the window and grill me, staring at my feet in absolute disgust. OMG…it was the most MORTIFYING thing ever! Dan called me Cousin Eddie from Christmas Vacation. Yea….yup.


Needless to say, for dinner that night all I wanted to do was class it up and try to redeem myself. I went with all black and cleavage. I wore the same black top from earlier without the bandeau. I paired it with these super adorable while also ridiculously comfy pants, the same nude Zara heels and my nude YSL clutch. I kept my accessories to a minimum with one layered necklace and a gold watch.

Day 6: Coliseum & Roman Forum; Dinner at Piazza Navona


Our last day was a beautiful, warm day where I would have died to wear flip flops, alas, I knew better. I couldn’t do another full of heels so I pretty much planned my whole outfit around my Chucks. I finally retired the leggings I’d been sweating through for far too long and wore this pair from Victoria’s Secret PINK. I topped them with a grey tank top worn underneath a chambray top. Simple, comfy and perfect for the day’s miles of hill and step climbing. I carried my little Gucci makeup bag as a makeshift clutch because it was small enough to grip tightly in one hand.

For dinner that night I kept it simple and covered with leggings, booties and a long sleeved flowy top. This top did show a small pop of skin in the back as it has one of those butterfly backs. I paired it with the same gold necklaces from Swell I’d been wearing most nights.

So! That’s pretty much it. Do you have any go-to outfits for travel? How do you get inspiration for what to wear/what to pack?