As Allie: Two Week Business Trip Without Checking Luggage

I need help putting together a travel wardrobe for the following trip this August that will all fit in a carry-on and I sure hope you can help me. I'm dealing with 2 very different climates and both business and leisure situations:

1. Fly to Honolulu where I'm speaking at a national convention for my professional association. I would typically wear a suit for the presentation, but I'm guessing everyone will be more casual given the location.
2. Two days sightseeing in Honolulu.
3. Fly to Maui where we're spending three days at a beach resort for some R&R.
4. Fly to San Francisco where I'm speaking at a different national convention. This one is usually pretty straight laced and formal, but I'm loathed to bring a suit just for a two-hour presentation. I'll also be attending a cocktail reception and going to dinner at a few dressy places.
5. Two days sightseeing in San Francisco then fly back home.

I checked out the weather in San Francisco for August, and days are in the low 70s and evenings in the 50s with a relatively low chance for precipitation, and most precipitation will just be a light drizzle. Honolulu and Maui will be high 80s during the day and high 70s at night with a very low chance of any sort of precipitation. Considering the suggestions I have in my two-week vacation in one carry-on bag post, I created this capsule wardrobe:
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It’s easiest to pack if you stick with a single color story. I decided to choose cool tones and neutrals for this collection. As with my two-week vacation wardrobe post, I stuck to fabrics that are versatile, washable and wrinkle-resistant – ponte knit, silk, crepe and traditional jersey.
While I understand your desire to not pack a suit, a ponte suit in deep black free of decoration can look professional and sleek while being able to survive a long trip, and is also easy to mix and match. For the convention in Hawaii, you can wear the black ponte blazer with the blue dress and black pumps for a more relaxed look; for the San Francisco convention wear the black ponte blazer and trousers with the pumps and the blue silk shell.
For sightseeing and R&R in Hawaii, I gave you a variety of pieces that can mix and match. I created this capsule assuming you have access to laundry services at the hotels so pieces can be cleaned and re-worn in different manners, or can be spot cleaned in a pinch in your hotel bathroom sink. Both pairs of shorts are a bit longer to make them comfortable for long walks, hikes, bike rides, and other activities. The black shorts can even be worn with one of the silky tops for a more casual dinner or a night at a bar. Choosing a beach coverup that can double as a dress extends your wardrobe. I only have one pair of casual shoes for Hawaii in the mix; if you have room you may want to throw in a pair of flip flops for the beach and pool.

1. Coverup dress and sandals
2. Striped tee, black shorts, sandals
3. Printed tank, denim shorts, sandals
4. Teal tee, denim shorts, sandals
5. Printed tank, black shorts, sandals
6. White jeans, printed tank, sandals
7. White jeans, striped tee, sandals

For sightseeing in San Francisco, you can wear a lot of the same things for Hawaii, but add the cardigan or the white jeans for a bit more warmth. I put in a pair of Tieks flats in a soft gold – they take up no space in a bag, are very comfortable, and will keep your feet warmer than in sandals when in California. 

1. Printed tank, black cardigan, black shorts, sandals
2. Striped tee, white jeans, black blazer, ballet flats
3. Blue dress, black cardigan, ballet flats
4. Teal tee, white jeans, ballet flats

For both locations, I made the sightseeing and R&R clothes pretty classic and veering on conservative since you will likely be spending that time with coworkers and doing a bit of casual networking.
For dinners out and social occasions, you have a pretty good variety, from white jeans and a silky blouse with sandals, to a crepe jersey cocktail dress with a sparkly statement necklace. Having two small polished bags on hand (a dressier clutch and a leather crossbody in black) helps up the dressiness factor with most of your wardrobe. A pashmina can be worn with a simple tee shirt, jeans, and flats for a day look, can be your plane blanket, and can also be your shawl for the cocktail affair. I specifically chose gray which can better dress up than a bold color.

1. Blue silk shell, white jeans, ballet flats
2. Blue dress, black sandals
3. Blue silk shell, black pants, statement necklace, pumps
4. Printed camisole, white jeansblack sandals
5. Black crepe dress, black pumps
6. Blue dress, statement necklace, black pumps
7. Striped tee, black blazer, white jeans, black pumps
8. Black pantsuit (jacket buttoned), statement necklace, black pumps

Speaking of bags, consider a packable tote or mesh market bag, which can double as a beach bag or for shopping. It takes up little space and is quick drying. Choose a dark color or a color that complements your bathing suit for a more purposeful and cohesive look.
One of the best ways to save space for a trip is to simplify your beauty routine. Since you have situations where you need to make a professional impression, you may want to make a very specific choice regarding your hair. When I used to travel on business, I would pack a bottle of styling lotion to make air-dry waves for casual times, but pack a mini flat iron to make my hair sleek and straight for presentations. This way I didn’t have to pack my entire bathroom to get a specific look. It also is worth it to get a cut and color touch-up before your trip so you don’t have to work so hard on a polished style. As I mention in the two-week vacation capsule wardrobe post, rely on your hotel for some toiletries and amenities – call ahead to see if you’ll have a dryer, razor, shower gel, etc.
Wear the biggest and heaviest things on the plane flights. Don’t have one of the small purses as your “personal bag” for the flight, make it as large as possible while still being acceptable to the airline. Pack your purses with your underpinnings to help them keep their shape and maximize space in your bag. Choose a soft bag which can expand nicely and also smush well into an overhead compartment. Buy sunscreen and such when at your destination and leave the bottle when you head home.

Have you had to pack for a similar type of trip? Any suggestions or tips on how to pack for such an occasion?

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