How-To: Get That ‘On Vacation In Italy’ Look (Even If You’re Stuck Stateside)

Apparently all of you are going to Italy this summer! (Seriously, I feel like I get an email every week with Italy-related questions.) I’m jealous. But also happy to live (and dress) vicariously through you.

Q. Hi Jordan,

My family is traveling to Italy in two weeks and I want to look fabulous without trying too hard. What would you recommend?



A. I think when traveling in Europe it’s always nice to err on the side of classic and tailored – the point is to look like an extra in Roman Holiday…not Jersey Shore Goes To Italy, or whatever that (very fantastic, save for the clothing) season was called. I’d suggest skipping anything too short or tight, and honestly? I’d leave the sneakers at home and go for comfortable (but chic) sandals.

Most of all, remember two things: 1) HOT, and 2) COBBLESTONES. So think light layers, natural (and hand-washable!) fabrics, and at least passably sturdy shoes (you’ll definitely see women wearing sky-high heels in Italy, but flats can look just as lovely – and are much better-suited to sightseeing – if you choose the right ones).

First, let’s take a little stroll down memory lane and check out some of my sartorial choices – from the arguably decent to the most certainly ill-advised – from my own trip to Italy. Let’s also keep in mind that this trip took place a good decade ago, hence the heavy reliance on palazzo pants and chokers.

This is a ridiculous ‘look-at-me-gazing-at-the-horizon’ picture. But although the look is a little dated, I’d still wear these basics – relaxed-fit neutrals, pop of color with jewelry, cute-but-comfortable sandals, nice leather bag – were I hanging out in Venice today.

Sunburned me and Mama eating pasta in a blackout, posted for no reason other than that I love this picture. And was clearly loving that spaghetti.

When I put on this outfit for our last night in Italy, I remember feeling like a total supermodel.  I seriously thought it was the chicest thing ever. And while I’d probably put the look together a little differently nowadays, I still enjoy the basic elements of a white tunic over black pants with a fringe shawl and side-parted, slicked-down hair.

Also check out Mom’s stripes-and-leather look; love it.

And finally, here’s what not to do: wander around Florence wearing a teeny-tiny dress and sporty flip-flops, only to find yourself donning one of those lovely disposable shift-y things in order to gain entry to an arm cover-requiring tourist destination. Very nice of the vendors outside to provide these things for inappropriately-attired tourists such as myself, but wearing what amounts to a blue toilet seat cover can really ruin a look.

What To Wear: Trip To Italy 2

What To Wear: Trip To Italy

If you prefer pants, try skinny, stretchy styles in light colors and fabrics (no heavy denim; you’ll turn into a sweat puddle on those lovely aforementioned cobblestones), and add pops of color with your shoes and sunglasses.

And if you’re into dresses (how adorable are those?!), go for slightly more tailored styles, or add a belt to a loose shift) to pull the look together.

2-3 light, summery dresses

1 pair comfortable, lightweight stretch jeans (capri or ankle-length)

2 pairs shorts

5-6 tanks and tees in neutral colors

1 nice outfit to wear out at night if you end up somewhere fancy

1-2 lightweight sweaters

1 shawl (for covering up at night and in certain tourist spots where you may not be permitted to show your arms)

2 pairs flat sandals (1 sturdy-ish, 1 fancier)

1 pair heels (for aforementioned fancy night out)

1 bathing suit

Minimal accessories (because you’ll probably pick up some scarves/jewelry/belts/bags on your travels)

1 roomy bag for day

1 clutch for evening

Product info after the jump.

Miso print dress
25 –

MES DEMOISELLES cotton slip dress
$365 –

Vila Clothes red striped dress
30 –

ASOS flat shoes
$61 –

H&M flat shoes
25 –

Satchel handbag
$48 –

Nine west watch
$39 –

Mango aviator sunglasses
15 –

ASOS retro shades
$21 –

Brown sunglasses
10 –

Tie top
$52 –

Reiss scoop neck tank
49 –

Scoop neck tank
18 CAD –

Theyskens’ theory mid rise jeans
$84 –

White jeans
$80 –

K. Jacques flat sandals
$245 –

H&M flat shoes
7.99 –

Tom ford sunglasses
390 CAD –

L.G.R leopard print sunglasses
259 –
  • Tesia

    As an American who’s been living in Europe for the past ten years, I was so happy to see the clothes that you recommened for visiting Italy! I’ve seen waaaay too many poorly dressed American tourists on this continent (not to say that Europeans always dress perfectly…) and can only second your opinion of what to wear and what to avoid. Just one thing to add: avoid most backpacks and fanny packs – they scream tourist and make pickpocketing just that much easier. For anybody looking for more inspriation on how stylish Italian women (and men) dress, the blogs “The Sartorialist” and “All The Pretty Birds” have a lot of photgraphes from the streets of Florece, Milan, Rome, etc. I hope everybody enjoys their vacation on this side of the Atlantic! 😉

  • Francine

    Your mother = hottie.

  • Adeline

    That last image  brought back memories! I once visited a Florence church with my parents, only to have one of the assistants literally run after me with one of those plastic things.. (was wearing a tank top and had absolutely no idea one isn’t supposed to show bare shoulders in a church)

    And these are great choices! To the reader, bear in mind that Italy is hot (!) so def bring loose items, light fabrics but also things to protect from the sun if needed.

  • Allison Leweke

    This is perfect! Thanks so much, Jordan!


    • jordanreid

      my pleasure! enjoy your trip 🙂

  • Lauren

    Hi Jordan,

    I’m so frustrated by all the super-short dresses that seem to be in style this season. I love the look of the Miso print dress, but when you look at it on the model it’s a good 8 inches above her knee. I can’t be the only person who would feel uncomfortable in that – god, could you imagine bending to pick something up!?

    Anyway, do you have any recommendations of brands or styles of dresses for people who’d prefer at the knee or slightly above length. Whether you’re over a certain height, age or weight, it’s really hard to feel comfortable in a dress that’s just too darn short. Would love to hear your thoughts! Thanks!!

  • JM

    One thing I would recommend: leave your American sunscreens (and face wash, lotions, etc.) home! Europe has stricter guidelines in place banning harmful chemicals in their beauty products. They also have some beautiful sunscreens with safer chemicals that cannot be found in the states. Even ‘imported” brands such as La Roche-Posay use different compounds, adhering to stricter EU guidelines. One of my favorite parts about living in Europe is having access to safer products. Do yourself and your health a favor and stock up while you are there!

    • jordanreid

      great advice!

  • Renato Cuomo

    good! Fabulous post… regards from Italy!! //