My Mexican tan is fading fast but memories of days and nights spent in an all-inclusive haze remain (Editor’s Note: can life be all-inclusive? A one-time fee for access to all of the great playground that is New York? Consider it a membership. I’ll work on it). To honor these memories, I thought I’d share a fun handy-dandy guide to packing for the obsessive-compulsive.

Packing is a three step process for me:

First, I type up a maniacal list of things I need to bring with me for my long weekend/week/extended stay in paradise.

Second, I spend an evening trying on outfits and revising my selections. I’ve learned from experience that just throwing cute shit into my suitcase, although a fabulous idea, simply does not work, and it’s crucial to actually create outfits rather than bring individual pieces for travel.

Third, I meticulously organize all my essentials into satchels, pouches, and other compartments and proceed to stress out about forgetting something until I get to JFK and realize that although I remembered to bring 5 pairs of shoes, I did not remember to bring undewear, and have to purchase overpriced Hanky Panky knockoffs at the duty-free. C’est la vie.

Somewhere in between steps two and  three, I decided to photo-document the process for you. My tricks for fitting a week’s worth of outfits into a carry on are simple: lots of neutrals, and lots of statement accessories.

Observe.

1. The Carry-On Tote:

[Carry-On Tote: Rebecca Minkoff, Essentials: Scarf, Fedora, Flippy Floppies, Book, 2 Magazines, iPad (I get distracted easily), makeup pouch, pouch full of essentials such as meds/bandaids/mints/stainsticks/USB drives w copies of all my documents/etc (for full pouch contents and proof of insanity, see this post), sunglasses, re-usable water bottle] 

2. The Accessories

When you don’t have much room for apparel, accessories will really make your outfits stand out and will allow you to repeat-wear items but get a totally different look.

[Bling: Various department stores, boutiques, and flea markets. I love me a good flea market bauble. Artists & Fleas in BK is the best, although I’ve recently been super into e-market Bauble Bar]

[Shoes: For a week long tropical trip, I like to go for neutral shoes for all occasions. Top Row: Black Dolce Vita Wedges, Nude Loeffler Randall Heels, Tan Dolce Vita Wedges. Bottom Row: The Gap x Keds sneaks for exploring, random Loehmann’s flip flops for the beach, MIA and Marc Jacobs flat sandals for evenings spent at the hotel bar. I usually throw in a pair of sneakers too, but this trip was full of barefoot jogs and beach yoga, giving me room to bring more shoes than I normally would]

[Purses: Bottega Veneta, Tory Burch & a Marc by Marc Jacobs iPad Case (he makes awesome ones, check em out)]

3. Everything Else 

I try to bring two or three favorite standout pieces and a ton that I can mix and match. This is easiest for tropical trips, since silk camis take up considerably less space than bulky sweaters. As a rule of thumb, I like to bring 4 of each for a week long trip: jackets/blazers, tops, skirts/shorts, bottoms, dresses–this gives me more than enough room to create outfits for day, night, and cocktail hour.

[Jackets & vests in earth-tones]

[Easy summertime dresses and rompers]

[Lightweight and breezy tops]

[Cool shorts for the pool and the bar–how fun are the watercolor ones?]

[My most resort-friendly bottoms: white jeans, boyfriend jeans, floral jeans, and a chiffon maxi skirt]

Well, that was enough to have me seriously stalking Expedia for spontaneous Memorial Day flights. St. Bart’s, anyone? For the fellow obsessive-compulsives, I hope this helped. For normal people who just throw some crap into their carry-on and go, I hope you’ll still be my friend. Au revoir!