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Personal Shopper: Travel Wardrobe & Versatile Wedding Guest Dress

Bee Writes: Firstly, I love your site what a find it was i managed to populate my Christmas wish list entirely from items i found on it. I have a challenge for you, i am currently based in Australia but am packing up shop for 6 months and heading around the world in a post MBA celebration. My challenge for you is two fold:

a) I'm discarding all my crappy nasty clothes and was hoping you could maybe point me in the right direction for the minimal essential items that will get me through summer in South america, USA, and Canada and winter in Europe whilst only weighing in at 20 kg's.

b) This trip of seeming extravagance has been launched by three can't miss weddings my brother's in Boston in September, and my two best friends, one in July in Portugal (Hot) and one in November in England (Cold). I need an outfit i can wear to all three. I would normally pick three separate outfits but weight restrictions won't allow it.

Bee it sounds like you've got one hell of an adventure coming up! We've got a game plan for your globe trotting. Get basics in cotton and knit that will wear nicely and wash like a dream (also will de-wrinkle a few minutes after putting them on). Throw in a few tops and bottoms that are a bit dressier and/or sexier so you can get sassy when necessary. For most of the clothing I stuck to the Gap family of merchants (Gap, Old Navy, Banana Republic, Athleta, and Piperlime). I know you're in Australia and this will save you like a gagillion dollars in shipping.

There aren't any "winter" items in the selection. Our advice on that front is to buy as you go. Taking up precious space with items you won't need for a long time isn't worth the hassle. You'll be in Boston in the fall - plan it so you have some time to shop while you're there. You'll find all the cold weather stuff you could want, if you need to make room, ship some of the summer stuff back to a friend at home. Trust me, it's a world easier than lugging around pounds of clothing you won't need for three months.

Tops: Old Navy has great basics that run between $8 and $20. Their 3/4 Boat Neck Tee (1, $14) is a particular favorite). Find a few styles you like and buy 1 or two in your favorite colors. The Open-Front Jersey Cardigan (2, $17) is lightweight, but will be perfect for chilly nights and will go with everything. Toss in a couple of fun prints like the slub knit top (3, $19).

Bottoms: Gap Long and Lean Jeans (4, $69) in a dark wash will serve you for chillier days and nights when you want to up the hotness points. The Bodega Skirt (5, $24) is light and comfortable and will pair perfectly with pretty much any top (I'd buy two in different colors - a neutral and a fun color). The Silence and Noise Zipper Mini Skirt (6, $38) is another versatile day-to-night item. Roll-up Shorts (7, $39) and Skimmers (8, $39) offer you some options for those stick-hot days in Portugal.

Casual Dresses: Again, some options for dressing up, but still casual enough you can wear them during the day. The Old Navy Cross Front Jersey Dress (9, $19) is cute and airy. The Santorini Dress (10, $98) is a little fancier, but just as comfortable.

Shoes: We've only picked out two, one is a slip on sneaker Lacoste Marthe Sneaker (11, $54) and the other is a pewter flat Naturalizer Mystic Flat (12, $69) that you could both wear out and about and to a nice dinner.

Wedding Guest Dress: We picked out two dresses, both in silk, which will need a bit of a ironing out after your travels, but both frocks are super light and are perfect for pretty much any wedding. The first is the Confetti Dress from Boden (13, $218) and the second comes from Banana Republic's Monogram Collection (14, $126). For your cold weather wedding match whatever dress you choose with a pashmina and hose.

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