Ah… for me, there’s no vacation that I enjoy more than a cruise. Maybe its the constant attention of the staff… maybe its the fact that food is literally being thrown into my mouth 24/7… or maybe its the notion that other than remembering to wake up, go to sleep, and use the bathroom, I’ve been given a week completely devoid of responsibility.

The only responsibility that I take incredibly seriously when on a cruise is deciding what to wear. When else is it appropriate to wear a giant flower in my hair at all times? So many activities to partake in, and so many different outfits that I will need to change into for said activities.

I’ve been known to change my outfit 5 times in one day when on a cruise. Casual capris for breakfast… swimsuit-y for mid-day… a cute sundress for a shore excursion… a dressy ensemble for dinner… sweats and a tank for late night gambling and eating. When I’m on a cruise I like to think of myself as, say, the hostess of the Oscars. Damn, they change their dresses probably 10 times during a three hour show! Imagine how many wardrobe changes I’ll need for a 9 day Caribbean cruise. The possibilities are just endless.

Endless indeed, but I’ve broken it down for you into some “must have” items for a cruise (or any vacation really, but might I recommend a cruise??) Naturally, I bring at least 10 of each item (10 shirts, 10 pants, 10 skirts, etc) and I’m not admitting it, but I may have also, in the past, packed detergent so that I could do laundry and re-wear items while at sea. Hey, who knew I wanted to wear my white cotton Loft skirt on day one AND on day 7??

Below, I’m sharing with you some of my favorite photos from past cruises and vacations. I hope these, and the picks below, inspire you to do some vacation booking and then some vacation shopping! After all, July 4th is right around the corner, and we all know that’s when summer clothes go on clearance.

Aw, here we are in the Dominican Republic petting Nicolle the sea lion. She’s adorable, and so is my versatile outfit. I’ve paired a simple cotton skirt (Old navy) with a tankini top (Jcrew) The top is super appropriate to wear around the ship, and on shore, and when it was time to hop into the water and swim with the sea lions, I was ready to go.

If I’m going to be touring a sunny destination, I make sure to pack some strapless tops; No one likes ugly tan lines. Top, American Rag; Skirt, Loft.

Embrace the formal nights on board! I get sickened when I see people in plain old black pants and a blouse on formal night. You wear that to work everyday! How often do you get to wear a cocktail dress, or, even better, a gown?? Here I am in a favorite silk dress, from Marshalls.

When choosing colors, think TROPICAL. You’re going to get some color on the boat (unless you’re pallid like me) so pick something that’s going to look awesome with a tan. Here I am in a bright turquoise strapless top from Loft. I’m pretty sure someone took this top at bookclub last month, so whoever that is – you should book a cruise and wear this top while you’re there.

Love a simple black cotton dress for vacationing – you can dress it up, or dress it down, as I have here, in flipflops from Haviaianiaaiiaiiaas. I can’t spell that word, so I’m not even going to attempt it. Dress, Marshalls.

Enough about me… Lets talk about clothes that YOU want to purchase for your upcoming vacation. Remember: I firmly suggest you book a cruise, and possibly invite me.

This dress, from Loft, is not something I’d normally wear in my everyday life. Its kind of hard to justify a white dress with a bunch of flowers on the side in an office environment; on a cruise, though, this is, like, the best dress ever. Flowers = tropical. White = makes you look tanner. Pair it with some wedge sandals and you’re ready to walk around Old San Juan and do some shopping.

I may have mentioned in the past that I love the whole one shoulder look. This dress, I think, is just stunning. I’d dress it up for dinner w/the Captain by adding big gold earrings, a chunky gold bangle bracelet, and some neutral colored spikey heels. Dress, Loft.

Ahoy matey! This dress, from Gap, makes me want to push the captain out of the way and take over steering that giant wheel thing.

This is a great dress up/dress down frock from American Eagle. I’d wear it with chocolate colored strappy sandals.

Aside from the prom and your wedding, there aren’t too many opportunities where you can get away with wearing an all out ballgown and not have people looking at you sideways. I always try to go all out for at least one of the formal nights on a cruise. Bcbg makes some of the most stunning formal gowns. This one is formal, and yet appears light and airy.

Make sure you pack an ample amount of cute tanks. If you’re like me (aka an A-cup) you probably love shirts with built-in shelf bras. If you don’t (and this means I hate you, you large busted gal, you) then you can obviously throw a bra on under any of these tops.

I think this is just so sweet and cute, from Victorias secret. I’m probably going to order it this week, and I’ll wear it with full length tan linen pants.

Tanlines? Not in this top, also from VS.com.

This does not have a built in bra (oh well) but is still very cute and nautical. It’d look adorable with a short, white denim skirt and flipflops. Top, Old Navy.

I’ve said it before and I’ll say it again for all of my small chested friends out there. These bra camis, from Old Navy, are the BEST around. I’m actually wearing one right now as I type this. A black one. I swear. They’re comfortable, soft, wash well, and they even have enough support for a workout. And they’re not super short so that the bottom of your belly is hanging out. No one wants to see that. Whenever they’re on sale (sometimes they’re 2 for $20) I always stock up. You should too!

Sometimes it gets a little chilly when you’re inside the ship. You should definitely pack a cardigan or two to throw over your shoulders when you’re wandering the boat decks at 1am. This summery coral cardigan is from Old Navy.

I’m not a shorts girl. You’ll never find a pair of shorts anywhere in my closet, or in my blog. Shorts are the work of Satan. He wants the world to see my cellulite, and I’m just not having it.

My favorite summer alternative to shorts is the cute, casual skirt. This yellow number (and it comes in other colors) is from Old Navy, and would be perfect with a cami and flip flops for hanging around by the bar drinking something pineappley out of a coconut.

If this skirt doesn’t scream “CRUISE” then I don’t know what does. Old Navy.

Linen pants are a great cruise staple. I even walk around in linen pants and a bathing suit top, and I don’t feel ashamed. These are from VS.com.

Another linen alternative, from Joie. I feel comfortable just looking at these pants.

Cropped khakis from VS.com – I actually like her whole outfit. Unfortunately, the jacket and bag are NOT available on their homepage. Those tricksters.

You’re going on a cruise, so you’re going to have to suck it up and wear a swimsuit. I know, I hate it too. I have to tell you that if you want to buy the best quality swimsuit out there, I’ve found that Jcrew is far and away the best value for the $$. I have one Jcrew suit that I bought as a Junior in college; its still in perfect condition and doesn’t look at all worn. This halter & skirted bottom combo, from Jcrew, is lovely if you want to hide some junk in the trunk. Unfortunately my trunk is so full that I’d need several of these skirts, but its cute none the less.

If I was 40 pounds thinner, I’d absolutely sport this suit on a cruise. Its so tropical. From American Eagle Outfitters.

Another cute suit from Jcrew. This girl looks like a zombie though, doesn’t she? I’m not buying this suit specifically because I don’t enjoy the model.

When ELSE but a cruise can you get away with wearing a giant floppy hat? I LOVE this one, from Juicy Couture. I need it, and you do also.

Nothing says vacation like a pretty new espadrille. This shoe would compliment any of the pants/skirts above. Sandal; Vince Camuto, available at Piperlime.com.

This sandal, from Nine West, gets rave reviews on Zappos for being super comfortable to walk in – a must if you’re doing shore excursions.

I wouldn’t dream of going on a cruise without a pair of my beloved Havianias.

And a matching pair for Emerson.

This straw clutch, from Serpui Marie, is a great evening bag for formal nights aboard.

This metallic woven tote, from Kate Spade, is perfect for a day shopping on shore. You should fill it with diamonds bought at 40% off in St. Thomas.

I hope that you look at this tote, also from Kate Spade, and think “Heather should own that.”

Its a cruise and therefore it is ok for you to carry a bag covered with lemons. Bag, Juicy Couture.

In summary, you should go on a cruise and wear all of the aforementioned items, or else I will make you walk the plank. I really wanted to work “walk the plank” into this blog somehow because, well, I just did. Anyway, happy shopping and happy cruising.