Yes, I packed like I was moving down there.
Let’s just start by saying that I might have packed a bit much, and did I really need 30 dresses? No, I didn’t, but a girl can never be too prepared. Did I wear it all? No. Did I still feel like I had nothing to wear? No, but I did feel like I had too many options on occasion, which may have overwhelmed me. I do this to myself; I’m perfectly aware of my flaws.
In the spirit of transparency (and because I love a vacation wardrobe recap for inspiration), here is everything I wore for a week in the Dominican Republic. And yes, everything is linked right here in my ShopMy because I am nothing if not completely committed to monetizing my overpacking skills.
Daytime Looks: Swimsuits & Coverups that became my entire personality
In the spirit of honesty, I lived in swimsuits and coverups because we had a private chef, a beautiful villa, and no need to get dressed during the day. In fact, I only actually got dressed in real clothes during the day once during our week down there because my husband and I decided to book a spa date for ourselves.
The real MVP of the week was my swimwear because I received so many compliments. And believe me when I tell you I did not spend much on that. Bikini tops from Target, bottoms from Victoria’s Secret, most of my cover-ups from Shein (and one fun Lilly Pulitzer because who doesn’t love color?). But in true Tiffany fashion, I accessorized with more high-end items to make it a little bit more me. I paired every swim look with my favorite Gucci sandals and my new Prada raffia tote bag (which was actually the perfect size for my accessories and everyone’s sunscreen and goggles).
Lesson Learned – Did I need to pack 14 bikinis? No, but I wasn’t re-wearing any of them because that’s not my vibe.
Evening Looks: Dresses, Dresses, and more Dresses
I was really proud of myself every evening because I did keep it simple. Actually, I think I always keep it pretty simple because I’m more of a classic items kind of girl, but you know what I mean. I had five great dinner looks for going out and one more casual look the evening our private chef made an al fresco dinner for us to enjoy by the pool in our villa. All of my looks were simple – the dresses spoke for themselves.
Out of my six dinner looks, three were designer looks from For Love and Lemons, Agua Bendita, and Bardot. The others were all straight from Shein, and I could not believe how much I liked them. They were all under $20, and all received just as many compliments as my designer looks. Once again, I paired them with my favorite Gucci sandals (though I did once wear a pair of Stuart Weitzman wedges) and my favorite YSL handbag, and my everyday jewelry.
What I didn’t wear
I did go a little overboard at Bloomingdale’s before we left, and I ended up not wearing a single dress I bought there. Worry not – I will wear them eventually. But I didn’t wear anything that was too heavy, and those materials were just heavier than I was comfortable wearing in the sweltering Dominican heat (which actually makes our Florida heat feel bearable).
I also did not even once wear sneakers or any of my workout clothes, and I didn’t wear the heels I packed.
My advice
Pick a color palette and stick to it. For me, it was neutrals such as whites and creams along with a lot of orange (and one very fun green dress). This helped me narrow down my packing to one bag to carry in the evenings, as well as narrowing down the number of shoes I brought (that I didn’t even wear).
And the question everyone’s been asking…
Tiffany, was your luggage overweight?
NO! For the first time in my entire life, my luggage was not overweight! It was 50 pounds exactly. That’s like…one out of 300 flights, but it’s a start. Now, we did fly American, and they are gracious enough to give everyone a free carry-on, so I did pack a full checked bag, added some of my stuff to my husband’s checked luggage, and spread the rest of my stuff out in my carry-on and my very large personal item handbag, but who’s counting?
Final thoughts
This trip was a great example of classic Tiffany packing. A mixture of high-end items (when in doubt, buy high-end shoes and accessories) and more affordable pieces that have the it factor. And, as always, when choosing affordable items, be sure you’re looking at material, weight, fit, and feel, because that’s what matters. A cheap dress that looks cheap never sells, but a cheap dress that fits, holds its form, and looks good is always a good choice. Just like a $400 dress that’s ill-fitting can look cheap and tacky, fit is everything. And you know my motto…if it fits in your luggage, bring it.
Tiffany Raiford 