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?

Thanks,

Allie

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.

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.