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Episode #150: What to Wear in Italy: A Guide to Planning your Italy Trip Outfits

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What to wear on your trip to Italy? The short answer is – whatever you like! But while we all want to feel comfortable when we’re on vacation, it is a time when more photos than usual are being taken and you’re eating out more than you would at home, so we also want to feel great in what we’re wearing. The type of items you pack makes a huge difference in feeling both comfortable and stylish during your time in Italy, not to mention helping with the notorious challenge of fitting everything into your luggage.

Show notes

For our 150th episode, we welcome back author Corinna Cooke, who writes the Glam Italia series of guides for Italy (most recently adding 101 Fabulous Things to do in Venice) and who runs boutique small tours all over Italy. In the past, Corinna has joined us for podcast episodes on itinerary planning (episode 53), finding inspiration for your trip (episode 104), and Italy travel hacks ( episode 116), but in this episode, we are talking about what to wear in Italy which is a topic that generates a lot of discussion on our Italy Travel Planning Community on Facebook. For many years Corinna has traveled to Italy regularly for long stints, traveling across the country, so has a lot of experience in packing under her belt. She has developed some amazing strategies and pinpointed fantastic products to streamline your packing, leaving you with a flexible and fun wardrobe for your trip to Italy (plus extra room in your suitcase for any purchases you make while there).

What you’ll learn in this episode

  1. It’s really worth thinking about your Italy travel wardrobe ahead of time so you can go with both the right things and with not too many things. You don’t want to wind up with really heavy suitcases – it can be hard work and stressful carrying so much stuff around. Also having too much stuff, especially stuff you then don’t wear, just gets in the way. It’s great to figure out what to bring and all those things working for you
  2. You might see people on blogs or Instagram who travel to Italy for weeks at a time, with carry-on only, and think ‘I could never do that!’ But their secret is simply that they’ve packed smart and whether you do carry-on only or have your checked luggage, making the right choices means keeping things light and outfits easy to put together You can end up having a lot of options if you’re playing the game the right way

Strategy

Start with the shoes

The very first step in your planning process is to figure out two pairs of shoes to take – and only two! At the very end, you can maybe add in a third pair, maybe an extra pair of sandals, but this process is based around just two pairs of shoes.

It cannot be stressed enough how important it is that you get your footwear right for a trip to Italy. You do so much walking and even when you’re in places that aren’t hill towns like in Tuscany or the Amalfi coast and are thought of as flat –  like Venice, Florence, and Rome, they still have lots of cobbled streets. So if you don’t have the right shoes that are supporting your feet, ankles, and lower back, you’re in for a world of trouble.

For your first shoe in the summertime, go for a smart-looking, supportive sneaker kind of shoe. You don’t want big, ugly ones, but the ones that are maybe white with a colored trim – something that looks nice but that has got really good support and you can walk 5 miles a day if needs be.
Which doesn’t mean you’re going to walk 5 miles, but if you do, you’re covered. You can find really stylish white sneakers. White sneakers tend to be a controversial topic for some reason, but Corinna and Katy both wear white sneakers, as does half of Italy – they go well with so many outfits. 

Make sure to break the shoe in and not take a spanking brand new pair with you. Even a shoe that will become comfortable can cause discomfort if doing. a lot of walking without breaking them in. In winter, go for waterproof sneakers. 

For your other pair of shoes, go for a really great, supportive pair of sandals and for winter travel, a good ankle boot, like a Chelsea boot with a good tread. Again make sure you break these shoes in ahead. of your trip. Your feet will thank you. There’s always a chance you’ll still get the odd blister, but if you haven’t broken in your shoes, it will be a given. 

For both summer and winter, get shoes with a rubber tread as other tread types can mean you can slip, especially in the rain.

A couple of good brands (Australian) for comfy shoes that give a lot of support and are really stylish shoes are Bared and Frankie Four.

No ballet flats

If you  Google what to wear in Italy, it will so often come up with cut-off denim shorts and ballet flats. Neither of these is a great choice, and in particular ballet flats have got zero support. It’s difficult for people to really understand how bad their feet can get after even just a day of sight-seeing. If you’re thinking about bringing ballet flats, pop them on and go for a five-mile walk around your neighborhood and just see how your feet feel afterwards!

Moleskin

Another MVP (Most Valuable Player) to throw in your suitcase is Moleskin. This is a recent revelation to Corinna from a lady on a recent tour who carried a bandage-style roll of moleskin in her handbag and whipped it out and saved a lot of sore feet. When it’s very hot and humid if you put bandaids on. a blister, the bandaid rubs up and slides off in no time at all, on sweaty feet. With the moleskin, you cut a piece off, and put it over their blister, and you’re good to go. It gives a nice cushion, won’t peel away, and stays on all day. 

Alternate

Alternate the sandals and sneakers day to day to give your feet a rest from either.

Match your clothes to the shoes

Once you’ve got these two pairs of shoes figured out, pull out all the clothes that you think you might want to bring to Italy. Separate out whatever does not go with these two pairs of shoes. Rather than choosing your wardrobe and then figuring out the shoes to go with it, you’re doing it in reverse. Everything has to go with these two pairs of shoes.

Isolating your clothes options

Corinna uses a rolling rack, or you might have a laundry rack you could use or maybe make some spare space in your closet – wherever you chose, put all the things that you’re thinking about taking there. You’ve got to isolate it off so you can see it all and think about it. Corinna then usually spends a few days going back and forth, pulling things off trying them out to see if they go with the shoes, and putting them back only if they go. This narrows down all your clothing items to workable options. 

Fabrics

Once you’ve got those clothes set aside, it’s time to go through and now remove anything that is not travel-friendly.

Travel-friendly clothes mean fabrics that pack easily, that are low wrinkle, and are easy to launder (definitely no dry-clean-only items). Travel fabrics also tend to be temperature-regulating, and also tend to wick away more moisture from the skin. When it’s a hot and humid day and you’re perspiring, rather than holding it against you your skin, these travel fabrics tend to move the moisture away. 

Winter

In winter you tend to need fewer items and Corinna’s color palette in winter tends. to have more neutrals than in summer and more black. 

Merino wool

Merino is a great fabric generally but especially in winter. Corinna always wears a Merino Cami on long flights. Merino is really thin, so you’re not bulky, and it regulates temperature up to around 70 degrees Fahrenheit (20 degrees Celsius). So you can be going through hot and cold – for instance, it’s hot on the ground but then gets cold after the plane has taken off. You can find some really great thin Merino sweaters that are not much thicker than a heavy T-shirt, but are super warm, and they keep the moisture away too. 

J Crew do a fantastic Merino sweater called the Tippi which comes in all kinds of colors. Word about the Tippi has gotten out and they can go out of stock easily, so you need to get ahead on that one.

Other cold-weather fabrics

Fleece is a great insulator, dries quickly, and contains no animal products – a great option for cold weather.  Thinsulate and Gortex are other great fabrics. 

Pants

Ponte is a flexible fabric that moves with you but still stays quite structured. You can wear Ponte pants for more than one day in a row and you’re not going to get a saggy bottom or at the knees. This fabric really holds its shape, but it’s also stretchy and comfy, and you can get a really nice, smooth, kind of streamlined silhouette with it. They make these pants in all kinds of different shapes bootcut and skinny cut. They are no-iron pants, so when you do wash them, you just hang them, they dry overnight and no ironing is required. 

Jeans are probably only suitable in the wintertime, and you’d want to take just one pair. They normally take up a lot of space in a suitcase, and they weigh a fair amount. Dryers aren’t common in Italy so If you’re going to have to wash them, you may not get them dry unless you have a radiator to put them on.

So in winter, one pair of jeans and a couple of pairs of travel-friendly pants/trousers – like the Ponte pants.

Merino dresses

There’s a company called IBEX which make fantastic merino dresses. They have a merino dress with long sleeves which is perfect for wearing with tights and boots, with maybe a cami underneath, and throw on a leather jacket, you’re good to go and it keeps you really warm. If IBEX doesn’t have theirs out, which they don’t at the moment, you can just googling merino dresses and quite a few will pop up.

Puffer Jacket

Puffer jackets are really popular over in Italy and they’re great for travel because they roll down really small and are light and they are of course super warm. If you’re packing a big heavy coat, unless you need to have it on all day every day, it’s just a complete nuisance and takes up too much space. You can get puffer jackets that come down like mid-thigh as well as the shorter options. 

Umbrella & scarf

It’s a good idea to include an umbrella and scarf in your winter packing. You can buy cheap umbrellas when you are over there and get rid of them at the end, but a good travel umbrella is light, compact, good quality which means you don’t have to go looking for one. A good scarf is always brilliant for winter – great to keep a cold wind off your face and provide extra warmth.

Summer

Cotton

Although cotton seems like a good option, for travel it is better to have cotton that’s got something else mixed in with it, as cotton can sit against your skin which isn’t ideal in the heat. 

Linen is great. We know it is going to wrinkle, but the whole world knows linens going to wrinkle so you just roll with it. Loose linen dresses that move with you in the heat are fabulous for hot days – we want things that are going to move a little bit with you so you’re not getting sticky,  swollen, and frustrated.

Old-school man-made fabrics

Man-made fabrics like rayon and polyester have been around for a long time and have bad connotations of cheap and nasty clothes from decades ago. But the new generation versions of them are fantastic for travel. That doesn’t mean all rayons and all polyester items are great, but when you find travel clothing that’s got them in, they’re really good because they’re durable, wrinkle-resistant, and quick drying.

One of Corinna’s favorite travel items are Departure pants by Eddie Bauer, and there are tons of other brands that make them too – Googling Eddie Bauer departure pants and you’ll see some alternatives. These pants look really chic,  they keep their shape and don’t wrinkle. Corinna has been a fan of these pants for a long time, but having just checked the label, realizes they are indeed polyester. They’re great for travel because you can wash them out, hang them up, and they’ll be dry before the evening is over. Ideal if something happens like if somebody spills a glass of wine on you, you spill bolognese sauce on yourself, or whatever – when you have to wash something out, and you want something that’ll dry quickly and with no drama. 

There are some fantastic dresses that are made by an Australian company Ever by X, which are made of a technical silk, which is a recycled material, but looks like silk. It’s also a convertible dress, that goes seven ways and you can easily dress it up or dress it down. It comes in lots of different colors and styles and you just can wash it out and it dries overnight. 

These manmade fabrics are built to hold their structure. It’s not that wash it out and it looks like an old rag the next day – they hold their shape. Some other man-made fibers are Tencel, Modal, and Lyocell. These are made from wood pulp and are really brilliant fabrics. It used to be that Modal was really expensive, but now it’s in lots of things. Corinna has a t-shirt that is on her MVP list that she got from Amazon Essentials, a very inexpensive T-shirt made from cotton, modal, and spandex. You wash it and it goes right back into shape. She’s got one that went with her to Italy for four months this summer, in very hot and humid weather but is still gleaming white. Corinna has found that these products containing Modal products seem to hold their white really well.

The other MVP top that Corinna took with her to Italy this year is a tank that she got from Target for $5. She thought it would likely last for a few weeks, and she could then use it to do housework in afterwards, but it turned out to be a really great top that just lasts. Again it’s made from cotton and Modal. Many influencers also started popping up all over Instagram calling it the buy of the summer. You can still get them at the moment if you go online at Target (Corinna actually bought five more herself online this week). So you don’t have to spend a lot of money to get great travel clothing.

Not long ago the big designer brands would put out something like this, and they’d charge $95 for this kind of T-shirt or tank top and people wouldn’t blink at paying for it because you’re paying. for quality – it holds its shape, you can wear it a hundred times and it still looks new. In the last couple of years, you can get these things very inexpensively – they’re accessible to everybody.

Viscose/Rayon

Viscose is perfect for travel. It looks expensive, but it’s not and it’s really soft. It is a silk substitute and it also has some wood pulp in it. It can give the feel of a fabulous soft silk and so feels expensive too. 

Acetate and Spandex

There’s a company called Chicos that has a famous traveler’s clothing line made from this fabric. They have all these intermixing part – skirts and tops and dresses and pants etc. Again, you can simply wash it out, hang it up and it dries really quickly and keeps its shape. Corinna has had some of their pieces for years and years.

Capsule Wardrobe

The key to figuring out what to wear and making your travel packing work best for your trip is to create a travel capsule wardrobe – key pieces that you can mix and match. Find the pieces that work for your shape to get some great core products and then put some accent things with them for great, flexible wardrobe of clothes. 

Start by having a good pair of travel pants. You’re likely going to want to wear travel pants flying in and out, and on days when you’re moving about, taking the train for example. 

If you’re going into the summer and it’s going to be really hot, you’ll maybe want to wear a skirt instead, or something with movement. 
It’s great to have a few travel skirts with you that are good for lots of walking. Bias-cut skirts are fantastic for everybody’s body shape. Whatever size or shape you are, a skirt that’s cut on the bias, it’s going to give a little bit of movement around the knees, so you got a little bit of breeze and you’re not restricted and they tend to be very flattering.

For a standard trip of a couple of weeks, pick four bottoms and then five or six tops – you’ll want your tops to be able to go with at least three of those bottoms. Then you’ve got this great ability to mix and match and change things up.

Color and comfort

A lot of the items you see in ‘What to Pack when you Travel’ articles do not suit a lot of people and you just wouldn’t feel good in them. When you’re going on vacation feeling comfortable is key but you are going to be taking a whole lot more photos than what you would be doing at home and so you really want to feel your absolute best in whatever style yours is/what suits you.
A lot of people will say go for a really neutral palette, but why? Color is fun so if you like color, throw in plenty of color. Whilst Corinna likes bright colors, Katy prefers more classic colors – navies and whites. You need to stick to your own style and preferences in order to feel confident and relaxed. Sometimes people can decide they want a whole new vacation wardrobe, and they buy a whole lot of stuff that they don’t really feel right in. If you’re going to enjoy yourself and take great photos, then you need to feel comfortable.

Even if you like color, it’s good to have some neutral pieces and then have a bunch of colored pieces in order to mix and match. Neutrals can include things like white tops that go with all your bottoms. Don’t be afraid, as Corinna does, to buy the same top in different colors, especially when you find something you really like, you feel great in – you can then put that with your different bottoms. You’re rotating and maximizing what you’ve got. 

Find colors that look nice against your skin. Any color can have a million different hues and maybe 900,000 of those hues look bad against your skin, but then others really make your skin comes alive.

In summer, sundresses are a great option that you can wear during the day as they are nice and light or you can jazz them up to go out in the evening. You can swap them around and do all kinds of things with them. If you are someone that wears sleeves, get something that’s got a loose sleeve so it’s not restrictive in the summertime there it is hot and it is humid.

Respect the dress codes

If you do like to go sleeveless or wear shorter skirts or shorts, you do need to be aware that when you’re entering a church, as a matter of respect as well as often as per the rules, you need to cover your shoulders and your knees. If you’re going to the Vatican and other religious sites, they often will not allow you in if you aren’t covered – thighs and shoulders. It’s a cultural convention in Italy, and there are easy ways to deal with it – you can have a shawl or a scarf that you can wrap around your shoulders. 

Corinna always has a scarf tied around her bag, she carries a crossbody shoulder bag and it’s easy to tie it onto the handle and she can just whip it off when she’s going into places she needs it. Plan out what you’re wearing for the days you’re going to the Vatican or any church to make sure you’re prepared – because you don’t want to be rude or not be allowed in. As a visitor, you need to respect the culture of the country you are in. You might not be fined, or you may be allowed to enter the church, depending on who’s at the entrance, but why would you put all your energy into figuring out how to get around this convention?

The tour companies that Corinna uses will not take you to the Vatican if you show up to sign-in at their offices and you don’t have your shoulders and thighs covered, you’re kicked off and you don’t get your money back. They’re hardcore about it – even if they’re with Corinna who’s worked with these guides for over a decade. 

Back to black
Do take some black pieces – maybe a black pair of pants, a dress, a black skirt, because it is really serviceable. 

Wrapping up
in the summertime, you don’t need a jacket – though earlier or later in the year and on your travel days you may need to wrap up warmer. Corinna always has a denim jacket with her just in case, though it generally doesn’t get worn. A couple of little cardigans or wraps can be good at the very end of September and October or earlier in the year. 

Beachwear

If your trip includes a beach day or boat trip then plan a swimsuit that’s going to pack down really small. A lot of them have big built-in cups which can actually take up quite a bit of space – so ideally you want something that’s a little bit smaller. You’ll also need some kind of cover-up. You can take an easily packable beach bag or if you’re using a tote bag for flying/travel days, use that so you can double up the use and don’t need to take something extra. 

If you’re spending any real time at the beach then you may want to add flip-flops and something to use as a beach towel. The Turkish towels which feel like cotton but roll down really small are great – people also make them into sarongs and scarves so they can be useful in other ways.

Planning day by day

Plan on every piece getting worn four times. An average trip is maybe 14 days – so if you’re going for 14 days when you’re planning your wardrobe, plan on every piece getting worn two times. At least half of your outfits should mix and match, and they’ve all got to go with those two pairs of shoes.

Corinna has a box calendar on A4, that she puts all the dates in and then writes on each box where she will be on that day of the trip. She then writes in there what she’s going to be wearing. This helps you to figure it all out so that your repeats aren’t next to each other or too close to each other. It helps as well if something is going to have to be laundered you can work out which days you might have access to a washing machine etc. 

Then when you get up each morning, you don’t have to think about what you should be wearing for the day ahead. It’s one more travel stress that you can take away. You can hang it out the night before so that wrinkles drop out and you’re good to go in the morning – a huge time saver.

Where are you going

When planning your outfits, look to see where are the colorful places that we’re going to be that day. Are you going to be in the Cinque Terre, the Amalfi Coast, or in a Puglia port town – what will look good in photographs of that place? For instance, in sand-colored Matera, if you wear black it photographs like a dream with all that stone behind you.

Enjoy the space

It’s a bonus when you not only end up with this really condensed, really efficient wardrobe that you just feel great in every day while you’re gone but you’ll also that you’ll then have tons of room for your shopping. That’s what travel is all about – when you’re going to these fabulous places, being able to go, yeah, I’m going to buy that and bring it back because I got room in my suitcase – that’s great. Life is short and if you see something you like, get it – it’s so worthwhile because every time you get that something special out it’s going to put a smile on your face. 

About our guest – Corinna Cooke

Author Corinna Cooke is a favorite guest on Untold Italy. Originally from New Zealand she fell in love with Italy thanks to a high school art history teacher who introduced her to Italian Renaissance art. After moving to London and traveling throughout Europe, she couldn’t stop returning to her beloved Italy.

Now living in Phoenix in the United States, Corinna is a woman of many skills. She leads several Glam Italia small group tours to Italy each year and writes guidebooks of the same name exploring her favorite corners of beautiful Italia. And her “day job” is a make-up artist. But, her heart is always called to Italy. 101 Fabulous Things to do in Venice is her new book full of fascinating stories, tips, and tricks on how to have a fabulous time in Venice. 

You can find Corinna on these channels:

Corinna’s books


Stores mentioned in the show

  • Bared and Frankie4 – Australian brands with comfortable but stylish shoes
  • J Crew – US clothing brand
  • IBEX – make great Merino dresses
  • UNIQLO – fashion brand which has a range of travel wear and also HeatTech – thin garments which can work with your body temperature to keep you warm/cool depending on where you are
  • Canada Goose – for quality puffer jackets
  • Eddie Bauer– great brand for travel wear
  • Ever by X – a dress made from a man-made silk that can be worn in multiple ways
  • Amazon Essentials – you can get great priced travel-friendly items from Amazon Essentials
  • Target – US store
  • Chicos – great travel clothing line

Resources

  • Merino Wool – a kind of wool that naturally moderates your temperature
  • thinsulate – a brand of synthetic fiber thermal insulation used in clothes
  • Chelsea boots – these are close-fitting ankle boots with stretchy elastic side panels. Many have a tab at the back to allow for easy pulling on and off which is a design feature left over from their origins in Victorian times
  • ponte – a thick, double-knit fabric design
  • lyocell – originally trademarked in 1982 as Tencel is a man-made fiber, made from dissolving pulp and then reconstituting it by dry jet-wet spinning
  • modal – a bio-based fabric made from spinning beech tree cellulose. It is generally considered more eco-friendly than cotton because beech trees don’t require much water to grow
  • rayon/viscose – a semi-synthetic fiber, made from natural sources of regenerated cellulose, such as wood and agricultural products
  • What to wear in Italy Resources – get sent Corinna’s PDF with tips and strategies for your capsule wardrobe and a copy of her day by day calendar

Resources from Untold Italy

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