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How to Pack For Your Summer Getaway

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Still thinking about what to pack for BlogHer? In the comments on this post, Sassymonkey articulated what I'm sure is a common worry:

We're going to be gone for a whole week because we're heading to Chicago early to play tourist. That's a lot of clothes to pack when you are playing tourist vs not playing tourist. I'm not a good packer. I once, as a child, went away for the weekend and was not informed we'd be going to a wedding and ended up wearing the world's worst outfit ever. I'm still scarred. So I overpack. Always. And yet always forget something rather vital in addition to packing a whole lot of clothes I never wear. Sigh.

You really can pack for more than two days without needing a steamer trunk; it just takes planning. Oh don't roll your eyes at me -- it's not that hard. So whether you're Chicago-bound this summer, or heading somewhere else for a week or so, let's talk about how to decide what you'll take.

Start by making a list of everything you're planning to do on your trip. If you will be combining general touristy things with a wedding or conference or reunion, then include all that. Don't be daunted if you find that your list covers a lot of different kinds of events -- you don't want to get to your destination and realize that you're spending a week at the beach without a single swimsuit.

For example.

Once you've listed what you're doing, think about what you're going to wear. Three rules to follow when you get to this point:

Plan to be comfortable. If you know it will be hot at your destination, don't plan to wear pants for sightseeing, no matter how much you want to look like all those photos of Jackie Kennedy; pack shorts or skirts or little dresses.

Plan to be yourself. If you're not someone who ever wears a dress for day, then don't feel like you need to start now. If you love your shorts, pack them. By the same token, don't take a suitcase full of brand new clothes -- fill in blanks or replace what's not working, but for the most part, stick with pieces that are tried and true.

Plan to get dressed up at least once. It's not hard to pack a really beautiful embellished tee or a simple skirt or something that is a little more dressy than your touristy shorts and polo combination. This is a vacation, after all! Go ahead and celebrate.

What else?

Mix and match. Pack pieces that will work in more than one way: a pretty skirt that you can dress down with Keds and a tee for sightseeing, or dress up with a bright tank and some embellished sandals for night.

Layer, layer, layer. Virginia De Bolt has this very very smart suggestion: 

A sweater or a light jacket is a must for the folks like me who are in that stage of life where the blood moves awfully slow. Jeans, capris, really it's all okay, but have something with long sleeves for the air conditioning.

A cardigan or light jacket or pashmina scarf are all perfect options for layering.

Accessorize! Even if you're a jeans-and-tee girl, a really beautiful necklace or a cool pair of earrings can give your outfit a super cool edge.

Finally, the good stuff: Five things I am absolutely packing for BlogHer (and really, these are the five things I pack for pretty much every trip, with the exception of the beach, where I pack only swimsuits and pajamas -- seriously).

1. Cardigan.

2. Pashmina.

3. Pencil skirt.

4. Laptop-sized tote.

5. Pretty flats.

Want a more detailed list? Christie has a great one.

What five things do you always pack? What five things do you always regret not bringing? And next week: Organizing nitty gritty, or how to actually choose your outfits. (Can you tell that I have A System for packing? Because I totally do. 

Susan Wagner writes about style at The Working Closet and about chic suburban living at Friday Playdate. She can pack for a week in less than 20 minutes, but only because she spends weeks obsessing about it beforehand.

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KatieBeez 5 pts

I always pack my swim suit.  Summer or winter. Rain or shine.

Small black flip flops that take up hardly any space.  They are easy to put on to go for breakfast before you really awake or to go just down the hall, to the pool, to the hot tub, to the beach... 

Favorite jeans. 

Camis in white/light, brown and black.  

2 dress up outfits and whatever shoes are needed for them.

kayobe 5 pts

It's more than 5 but I tend to think of packing in units of functionality. The more flexibility and mix and match the better. Layers are key.

1. bathing suit, flip flops, coverup-dress, hat... in the off chance the hotel has a pool or jacuzzi or just a sunny spot to lay in the sun. All 4 items fit in the outside pocket of my suitcase so they're not taking up valuable inside space.

2. lounge pants, t-shirt, hoodie... it's so nice to be comfortable after a long day, they're suitable for running out for the paper and coffee and they can act as pj's too.

3. neutral pants, pashmina and cardigans...  mixing and matching will give you multiple outfit choices. Dressy jeans, black pants, beige cargo pants or shorts mixed with a black pashmina or cardigan and/or white cardigan. Color can from your tops and jewlery.

4. a dress... made of some material that can be rolled up into a ball and still look good!  Can be dressed up or down and paired with pashmina or cardigans and jewelry.

5.  comfy shoes... I'm a crocs gal. I have so many styles. Dressy flip flops work well too and don't take up much space.

6. backpack and clutch... backpack for day time by the pool or sightseeing and neutral clutch for evenings out.

sassymonkey 6 pts moderator

As much as I overall suck at packing the one thing that I always pack now is Soak soap ( http://www.soakwash.com/ ). A lingerie store in Toronto got me on to it. I use it for all my hand-washables at home but took it with me when I travelled to Europe. I can wash tanks and camis in the sink and throw them over the shower rod to dry. In europe we used it to wash socks, underwear and sweaters.

Somehow I have everything on your list. W00t! (Ok, almost flats, they have 1/4-inch heel.)

Sassymonkey ( http://sassymonkey.ca/ ) and Sassymonkey Reads ( http://sassymonkeyreads.ca/ ).