When my friend, Jacqui, asked me to write an article about what to wear on an Italian vacation…I was all in. Six couples are traveling by private bus over a 12-day period to Como, Siena, Sorrento, Capri, Positano, and the Amalfi coast.  Their one and only rule…no museums and no churches! Don’t you wish you were going, too?

So, of course, comfy clothes and shoes for the plane are a must. Athleta has fabulous travel pants that are super comfortable and don’t wrinkle.  Since planes can be chilly, wear them with a t-shirt and a long sleeve cardigan or a light weight jacket.  Jacqui chose a soft trench from Banana Republic Factory. Be sure to take a look at more jacket options from LL Bean and Tuckernuck on our Pinterest board.  

Their first three days will be spent in Como.  My advice is to make it simple and dress once for day and evening.  A pair of jeans, t-shirt, blazer and flats will do the trick. A cross-body or belt-bag is the safe way to go.  One of my favorites is a flat Hammitt cross body bag which can easily be worn under a jacket. And of course, we are sharing more bag options on our Pinterest board!

Striped pants and jeans are another versatile travel look.  Just add a shirt tied at the waist or a tee. For daytime add a denim jacket, and in the evenings, a comfy wrap from J McLaughlin.  Also think about wearing the pair of white sneakers you wore on the plane. To take your style up a tourist notch or two, add a neck scarf and a small straw clutch.


For their next excursion, our jetsetters will be traveling to Siena for four days of wine touring.  Dancing, dining, and diversions…oh my! This is where I suggest wearing a midi or maxi skirt with flats, slides, or sneakers.  It’s so easy to create multiple looks with a skirt. Repurpose one of the shirts you wore with your pants or jeans, and drape a denim jacket or blazer over your shoulders.  To add extra style, tie a knot at the hem on one side of your maxi skirt! Trust me on this one…no one will mistake you for an American tourist!

After a day trip to the Amalfi Coast, the travelers will spend the remainder of their trip in Sorrento at a hillside hotel with views of the sea.  The best way to pack for a long vacation is with a capsule wardrobe. My thought is to go with black and white or navy and white, and add a pop of color with your accessories.    Talbot’s black and white spring collection definitely adds a sophisticated flair to a capsule resort style. And for a fun daytime look, mix it up with checks and polka-dots. Add color with a pair of loafers or flats….I’m thinking red, or yellow, maybe green, or orange….you get the picture!

Hopefully, Jacqui’s trip will inspire you to start planning your next European vacay.  And be sure to message me if you need help organizing a capsule travel wardrobe!

Holley Williams is a personal stylist specializing in closet inventory, seasonal shopping, closet organization and wardrobe consultation.  Contact Holley at [email protected].  Be sure to check out Holley’s updated Pinterest board.