My Vacation Outfit Planning and Packing Tips

Every year around the middle of May, also known as now, I start to plan my summer. Counting Memorial Day and Labor Day, there are exactly fifteen weekends. I have three weddings, and what with birthday parties and housewarmings, six of my weekends are already accounted for — that means I better make the most of the other nine weekends.

While I don’t know exactly what I’ll be doing, I do know that I’ll be spending as little time as possible in San Francisco. Yes, I love living here, but I love warm weather (and everything that goes along with it, from swimming to grilling to sitting on a deck and drinking sangria) more than the fog and cold that is typical to SF during the summer. I would much rather spend my weekends lying by a lake or hanging on a beach than freezing in SF.

Since I can sometimes find a ride to the cabin in Arnold at the last minute, I keep my suitcase close, my travel makeup bag packed, and my closet ready. I’ve got packing down to a science. It’s the perfectionist Virgo in me that’s addicted to being an organized planner!

When I’m traveling for an occasion, like the aforementioned wedding, I, brace yourself this is totally crazy, make an outfit plan where I have every look decided before I arrive at the destination. I’d hate to miss half of the rehearsal dinner because I was in my hotel room trying to figure out what to wear! I also keep a packing list handy, so I never forget to pack random items like the camera cord or an extra eye mask. I’m currently working on making downloadable PDF’s of my outfit plan and packing list, but until they’re ready, I thought I would share my tips for packing. Here’s how I do it.

• Start by picking out the most important outfit. This will dictate the look and color scheme of the rest of your wardrobe for the trip. If you’re traveling for a wedding, the dress/shoes/handbag/jewelry you plan on wearing to the wedding is the most important outfit. If you’re traveling for fun, pick one event, a Saturday night on the town, an afternoon sailboating, an art gallery opening, and make this outfit the most important outfit.

• Pick the second most important outfit next and go on from there. Normally, I plan night outfits first, as nights are usually filled with events. For example, if attending the Food & Wine Classic in Aspen in June, I would need three night outfits: one look for the Thursday opening party, one look for Friday’s fancy dinner, and one look for Saturday’s Best New Chefs walk around tasting. Since all events are equally important, I would simply start with a favorite dress or top and decide which night it would be most appropriate for. Then, for the rest of the nights, I would pick different styles of clothing, alternating between dresses, pants, and skirts (I like variety!), but in the same color scheme. So this means that if I wear a maxi dress during the day, on Saturday night, I’ll wear either pants or a skirt.

• If the most important outfit involves gold jewelry and handbag, and black shoes and jacket, try to reuse these items in the next couple of outfits. Black and gold should be the running theme of the weekend. If the most important outfit involves navy and khaki, then choose clothing that matches this color scheme.

• You can always jazz up a tired color palate with a fun-printed scarf, fabulous floral top, or neon clutch. Be creative with the accessories!

• Select items, especially shoes, handbags, belts, jewelery, and jackets, that can be worn multiple times over the weekend.

• Pack as few shoes as possible. This is a hard one, believe me, but I try not to bring more than four pairs of shoes. Two heels and two flats.

• Think about the activities you will be doing. Sight seeing? You’ll need comfortable and flat walking shoes. Spending several days at the pool? You’ll need multiple bikinis and cover-ups, and maybe even a towel.

• When traveling by plane, always put a pair of socks in your carry-on and always bring a warm scarf that can double as a blanket with you to your seat. Checking your luggage? Always carry on your most important outfit and an extra look or two; this ensures that you won’t be devastated if the airline misplaces your suitcase.

• Once I’ve picked out all my outfits, I throw in one random, but matching dress, pair of pants, and party top, just in case the weather or events change at the last minute.

• Speaking of weather, check your destination’s climate and be sure to pack accordingly.

• Lay all of the clothes out in neat piles (party tops, dresses, pants, day tops, sweaters, under garments, etc.) on your bed before you place them in the suitcase.

• Leave a space in the suitcase for toiletries and makeup. These items are easy to forget and often times, can take up a lot of space.

• Turn delicate items, like silk dresses and knit tops, inside out so they don’t get snagged on a zipper, buckle, or shoe.

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