Will this be the first time my husband doesn’t have to pay for overweight luggage?
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Sorry, I was busy laughing because it’s highly unlikely. I’ve never packed light a day in my life, but I do try. The problem is that the Tiffany who packs her luggage doesn’t know which Tiffany is going to get dressed in on vacation. Skinny Tiffay? Bloated Tiffany? I don’t feel comfortable in this Tiffany? I have nothing to wear Tiffany? It’s really such a mystery.
But if there is one thing I’ve learned about packing for our travels, it’s that I like to think summer’s tropical vacations are much easier to pack for than our winter-weather vacations, and it’s a lie I tell myself. Winter packing is heavy and bulky, but tropical destination packing is just me adding 100 additional outfits to my luggage because I might get hot and sweaty and want to change. You never know.
I like to be prepared. Might I be chilly in a restaurant? Will evening golf cart rides be cool? I need comfy matching sweatsuit sets to lounge, and God forbid I pack fewer than 20 bikinis. Don’t even get me started on underwear. What if my body suddenly decides I have no control over my bathroom usage abilities, and I really do need 75 pairs? YOU NEVER KNOW.
As I’m packing in advance for our trip to the DR (between panic attacks over passport-gate), I can promise I did attempt to pack lightly. Heavy, heavy emphasis on the ‘attempt’. Did I mention I am horrible at pre-planning my vacation looks? Okay, okay…all my looks are in-the-moment decisions.
The good news is that we’ve officially reached the season of life in which everyone else in our household packs for themselves, and I’m no longer spending 3 days packing luggage for all the children (and reminding Craig to pack underwear). I make them a packing list of events, reservations, and plans, and they pack accordingly. What a gift.
But this time, I’ve actually decided to spend my three days of not packing for everyone else to pack for me, and so far this is what’s in my bag (minus swimsuits because I’m actually panicking about those right now, so we’ve moved on from those for the moment). I’m linking everything – and this time, I’m all over the place in terms of high-end and inexpensive pieces, and who is proud of Tiffany (not Craig when the luggage is inevitably overweight)?
Dinner Dresses
Dinners are going to be oceanfront, gorgeous, and absolutely stunning – and these are the dresses that spoke to me. I am pairing each of these dresses with one of two pairs of nude evening shoes – my longtime favorite Stuart Weitzman wedges that I bought over a decade ago, and a pair of Stuart Weitzman high-heeled sandals (look at me only packing two pairs of evening shoes!).
For Love and Lemons lace dress
This gorgeous maxi actually made an appearance in 30A during our spring break trip, but it was cool, and I didn’t feel like it really had its moment to shine, so it’s heading to the DR to make a statement. For Love and Lemons makes some of my favorite dresses, and it’s a brand absolutely worth the price tag.
Bardot maxi dress
I could not resist the entire silhouette when it came to this dress. It’s going to dinner – and it’s going to thrive. Bardot makes some of my absolute favorite dresses, and I’ve never met one I didn’t love immediately. It’s pricey – and many Bardot pieces run a little on the small side – but it’s absolutely worth the investment.
Floral maxi dress
When I saw this in an ad, I immediately wanted it. I wasn’t convinced I’d find the quality very good, and I figured it would go right back in the returns, but I actually really, really like it…and it was only $20!
Green Knit maxi dress
This was another impulse purchase I assumed I’d return because of the quality. It’s not great, but it’s better than I thought. It’s such a flattering dress, too. I decided to keep it, and I’m excited to take it to dinner with me one evening. The best part…the price. I’ll probably only wear it once, so it was worth the buy!
WEWOREWHAT Polka Dot maxi dress
Full disclosure: I didn’t think this dress would work, but I had to try it. I was pleasantly surprised by how well it fits and how much more flattering it is on than it was on the hanger. I’m in love, and I cannot wait to wear it.
Casual Outfits
Sightseeing, brunches, and shopping can be a little warm, so I wanted comfortable, cute, fun outfits to wear that I can walk around in and hopefully not get too hot wearing. Each of these dresses will be paired with my nude Gucci sandals (and no additional casual shoes, can we please take a moment to be proud of me for that?)
Agua Bendita mini dress
I’m a sucker for Agua Bendita, and never have I purchased a piece from this brand that I am not completely in love with. This dress immediately gave me island vibes, so I knew I needed it.
AQUA lace midi dress
Easy, casual, and absolutely adorable. This is going to make a great shopping dress.
Alice and Olivia tassel dress
I am so obsessed with this dress…which actually hasn’t been delivered yet, but we aren’t going to focus on that small detail because we are putting our trust in the delivery drivers in charge of it.
Orange two-piece maxi dress
Another of the ‘I’ll probably hate it and send it back’ purchases turned me ordering it in several other colors. It’s so much better in real life than I thought it would be, and it’s under $25, so if it falls apart after one wear or one season, who cares?
Show Me Your Mumu Seashell dress
This dress is one everyone’s already seen me in, but it’s too good not to take with. I think I bought it last summer, but it might have been the summer before. I can’t remember, but that’s not the point. The point is this dress screams summer vacation, and it’s comfortable, cool, and absolutely adorable.
Bags
This is where I’m not going overboard. I’m bringing one to use at our villa pool and our beach, and one small bag I can carry both day and evening. I’m adding my luggage and my personal item as well because I do like to carry a large bag as my personal item when we fly.
Airport Handbag
I bought my Louis Vuitton Neverfull GM in 2008 to use as a diaper bag, and I used it through all four of the babies. These days, it is my go-to airport handbag because it fits so much. A blanket, my Kindle and blanket, my jewelry, and the smaller handbags I want to carry on vacation. Oh, and snacks. I can’t resist an airport snack store.
Everyday/Evening Bag
The Yves Saint Laurent Le 5 a 7 in smooth leather handbag is my current favorite (and my anniversary gift from my darling husband). It’s the perfect size for both day and night, and it goes with everything I’m packing to wear.
Pool/Beach Tote
This Prada crochet tote bag is something I’ve had my eye on for a while now, and I finally decided to make it mine. It’s perfect for my book, sunscreen, phone, and towel when we sit on the beach or if we decide to forgo our villa pool in favor of one of the resort pools.
Luggage
I will admit that we are using our very old, very worn, very sturdy DvF large luggage to check, but I decided I wanted a new carry-on bag this year. I grabbed this one during Amazon Prime Days, and I love it! It comes as a set of three pieces – and it’s perfect to fit my shoes and accessories.
And on a final note…
I didn’t link every single thing I’m packing, just the definites. I know me, and I already know I’ll add another dozen dresses. And I have to make decisions on swimsuits and cover-ups, but honestly, that’s not something I’m mentally prepared to do at the moment.
Additionally, I am not an accessories girl…I don’t really do jewelry. I like simple and classic, so I’ll wear my wedding rings, my diamond earrings, and the Tiffany’s necklace and charm bracelet that I always wear because they’re sentimental. My husband gifted me the necklace with its “A” charm when I was pregnant with Addison (and it just so happens to work for Ava, too).
The bracelet he surprised me with in 2012 when we took a trip to Las Vegas. He bought it for me with the Tiffany & Co. heart charm, and he’s added charms to it every time we visit the flagship store in NYC, as well as a “C” charm when the twins were born. Both pieces are so special to me, so I tend to wear those and nothing else.
I’ll also probably do another post with the other random items I’m bringing, such as my skincare and makeup and other tropical vacation necessities.
Tiffany Raiford 