Vacation Style

Day Time

For day time sight-seeing, I tend to stick to jean shorts with a tee or tank, or a light sun dress, paired with comfortable walking shoes (I’m a walker when I’m not at home). I’m generally not a sneakers girl (unless it’s raining or there is uneven terrain involved) so my walking shoes are usually Birkenstocks. Jeans shorts are a staple in any wardrobe and they are great for vacations. They can be matched with almost anything in terms of colour or print so get a little crazy with tops here! Plus they are generally inexpensive. I recommend a few pairs in varying shades of denim. If I’m doing a beach or pool day, of course, daywear would include a swimsuit, flip flops and a wide brim straw hat.

My daytime purse is usually a small cross body bag, but recently I purchased a hip pack (aka fanny pack) which is a great alternative and keeps the weight off my back and shoulders. Try to keep it small so you don’t end up totting too much around. My must-haves include a small wallet for some cash, ID and credit card; sunglasses; iPhone & portable charger; chapstick or lipgloss; mini sunscreen (safety first!); map. I am not a fan of backpacks except perhaps as a carryon bag – way too easy to over pack. Then you start brining a sweater, an umbrella, water bottle… Instead I tie a sweater or light rain jacket around my waist or slung over my purse and buy water as I go along. Plus I think of backpacks as something used by a child (but that’s just me).

Night Time

For evenings out, I like to dress up a little. Certainly more casual than I dress at home (including lighter makeup and jewelry) but still a change from my day wear. I stick to my tried and true looks as much as possible so I’m not fussing about it if I’m having one of those days. One or two maxi dresses, cropped white jeans, black stretchy pencil skirt, 4 or 5 dressier tank tops (including strapless bra), wide leg silky or linen pants… enough to be able to mix & match a little and get multiple wears out of an item.

For shoes, I pack dressier flats, of which I have a few neutral-tone colours. I used to bring heels or wedges but I found that I never wore them. They were just coming along for the ride! I mean, seriously, I don’t know how these European women walk on cobble stone in stilettos! Practice I suppose… And for an evening bag, I use a clutch or small fancier cross body bag, which still fits the items listed above (minus sunglasses). For this, I recommend a neutral colour: black, cream/beige, or tan so that it coordinates with as much as possible.

Packing for Day

2-4 pairs shorts or cropped pants (denim/cotton)

1 per day tanks/tees (cotton) (or sundresses)

1 or 2 sun dresses (or more if preferred)

3-4 swim suits for a week 

1-2 wraps/cover ups/tunics for the beach or pool

Shoes – Birkenstocks, sneakers, flip flops (beach)

1 small cross body bag or hip pack

Packing for Night

1 or 2 dresses (maxi or other)

1-2 pairs of jeans (cropped/ankle, white or blue)

4-5 dressier tank tops (for a two-week vacation)

1 pencil skirt (black, or other neutral)

1 silky or linen wide leg pants (full length)

3-4 pairs of dressier flat sandals

1 clutch or small dressy cross body purse


The Extras

Above talks about basic wardrobe selections when jet setting. But what about the extras?

Dustbags – for packing shoes

Laundry bag – for separating dirty clothes

Zipper bags – for all kinds of things

Bras – 3-4 styles/colours (incl strapless as applicable)

Underwear – min 1 per day + some extras just in case

Light sweater, neutral colour (not a hoody) (tip: wear on the plane)

Light rain jacket (just in case)

Wide brim sunhat or light neutral toned baseball cap

Foldable beach bag (tip: can double as carryon bag)

Jewelry – a few costume pieces that complement as many of the above wardrobe selections as possible (but not the items that are really expensive or near and dear to your heart, lest they are lost or stolen)

I won’t get into toiletries. To each their own. I will however strongly encourage you to minimize and downsize as much as possible.