Spring is here, and I am currently writing this poolside from Turks and Caicos, so I’m fully in the spring break, summer wardrobe, warm weather mindset. I am an East Coast girl born and raised - growing up my summer vacations consisted of rowing practices and boat trips, neither of which require a very curated summer wardrobe, and if it did, the pieces were more than likely from Charlotte Russe or Abercrombie. In college I did a co-op, so I never truly had a spring break. I was either doing an internship or taking classes. And then the entry into The Real World happened, and at that point I accepted that spring break was not going to happen. But, my family does a spring break trip every year, and while it is not a gaggle of drunken girls on the beach, I much prefer a rented house in Turks and Caicos with outings and excursions to 2 am clubbing and a week of debauchery. (One of the few perks of freelance is making my own schedule - I say few with a bit of a jaded outlook because I just did taxes and submitting a W-2 for the year is a dream in comparison). Before this year, my summer wardrobe consisted of a reliable rotation of vintage graphic tees, two pairs of cover up linen pants that I’ve had since high school, a white tank and a black tank, and a tiered white maxi skirt. I purchased a vintage Betsey Johnson dress at the Manhattan Vintage Show a few years ago, and that’s about the extent of my summer dresses. And I hate shorts. There, I’ve said it. So I never really know what to wear when the weather heats up. I end up wearing the same jeans I wear during the winter, just with a strappier shoe and a shorter sleeve. I am all about layers, and jackets, and boots, but 90º+ weather makes that a bit challenging.
So, as unnecessary as it might be, I set out on a journey to curate a collection of really good summer pieces prior to my trip. As a now 27 year old I felt it was time. And while they are intended for summer, I tried to pick pieces that I can still work into my wardrobe for cooler months during spring and fall.
Look 1
Arrival day. We arrived on the island just in time to unpack and go to dinner.
Here I am, in my linen best, satin flats and all on a sandy beach and in my element. My father had serious doubts about the practicality of the shoes for such a casual occasion, but I’ve decided that I actually do not care how casual a place might be - I will simply wear the outfit I want to wear.
A better shot for the details. The pants could use a steam, which I did in fact do before departing for dinner. I don’t care what anyone says, I always pack a steamer no matter the destination. Creased clothing is up there on my list of pet peeves. The top is a thrifted linen button down I got years ago. It has become a staple in my summer wardrobe - so easy to dress up like how I styled it here, or leave untucked and open as a cover up, which I did do later in the week for a boat trip. Similar option here, here, here, and here - I especially like the last option’s skinnier white stripe. The pants were a surprising gem - my younger sister actually bought these from Hollister for the trip and I borrowed them for dinner. I’ve been seriously hunting for the perfect linen pant, and despite the back elastic, these might be the winner. You won’t even see the elastic if you wear a belt!
And wow, what a great segway to talk about the one I am wearing. I snagged this absolutely amazing vintage Calderon cream-w-gold buckle belt on eBay for a whopping $9. I’ve hunted for another to link here and can’t find anything, so here are some similar options: 1, 2 (brown, but a stunning gold buckle), 3 (kind of obsessed with this one!!), 4, and 5. And to finish it off, I added my trusty Staud Scotty bag - I don’t think they sell it anymore but here’s a link to shop it secondhand. And the shoes are Zara (linked here). I know what you’re thinking - “you hate Zara, Kendall!” Try as I may, I am not immune to their really good designs. I’ve been dying to add flats to my wardrobe and have been seriously struggling to find options I like that also are not $500+. I know I’ll also keep these for a while, or at least until they get too scuffed up to wear, so despite their origin, I am quite happy with this purchase and they will absolutely be worn all summer.
Look 2
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When I’m on vacation I try to wear as many outfits as possible interchanging the options I brought, 1. to justify my poor packing abilities, and 2. because why not, it’s fun. This was my “morning beach walk and coffee run outfit”. The swimsuit is one of my go-to Same bikinis I bought on super sale last year. Apparently I have a thing for orange as soon as the weather gets warm. The pants are a favorite thrift find - $3 at Goodwill. The top is an old Milly button down I snagged at the end of my internship there (now many, many years ago, and still a summer staple), and the shoes are the Zara flats again to tie the orange back in.
Look 3
This was fancy dinner night. And I really just wanted an excuse to wear this outfit. I’ve been hunting for a maxi linen skirt for a few weeks and really tried to hunt down a good vintage option, but I came up empty. Usually I’d wait a bit longer, but I had a vacation vision. I found this Urban Outfitters style and I’m so glad I bought it. It’s surprisingly comfortable and easy to wear, and it can be easily made more casual with a tee or sweater. I also love this Banana Republic option and this Reformation version if you’re looking for dressier options. The vest is Aritzia, linked here, and I found this style on their site that I think I might like even more. The belt is vintage and I just purchased it from Seven Wonders - I think I need to stop myself on my belt journey. The flats are Zara again (I promise these are the only two pieces I’ve bought from them in months!) and again, they’re shockingly comfortable and will probably be my most-worn shoe this summer. And to tie the black accessories together, I threw on my trusty vintage Fendi baguette - with a scarf tied around to make it feel less winter-y.
Look 4
The white linen pants return - I cannot escape them. Another morning look - this time a dip in the pool instead of the beach, and another coffee run. And of course a bit of shopping, although the options were limited, which was probably for the best. Anyone else get into a vacation mindset and forget about all things budget? This is a pretty basic outfit, I admit that. But I’ve been wanting to do some hair scarves and this silk bandana print felt like a good way to make the look feel a bit more intentional. The suit is Aerie that I bought last year and it is so comfortable. I am a huge fan of their suits if you are looking for something simple and pretty inexpensive. And I am obsessed with this bag. A really good Goodwill purchase - A vintage 1970s looped leather tote for $9. It’s interwoven leather and surprisingly holds a lot - I used it for the boat and it easily held a beach towel. Linked similar here, here, and here.
Look 5
Another “overdressed” look according to my family, but a good one according to me. The top and pants are both old Buffalo Exchange finds. Wearing so many neutrals made it pretty easy to mix and match the few accessories I did bring. The pants are a really nice olive/brown color, and I love that they can lean either way depending on what I wear it with.
Look 6
I’ve written about my search for this top previously, and I’m so glad I hunted it down. I love the Doen cami, but the black sold out before I even figured out the brand. So I spent a bit of time on my favorite secondhand sites and snagged this Banana Republic version. The skirt is another vintage find from Unearth Vintage and I like that the flowy viscose lends itself to feeling casual despite the maxi length. And would you look at that! The same accessories are back.
Look 6
This outfit is probably the least exciting of them all. The pleated linen pants, Zara via Buffalo Exchange, a ribbed white tank, and some sort of jacket. This jacket is one the pieces I am most excited to style in the upcoming months, and this outfit does not truly do it justice. It’s a vintage denim jacket, but without the typical denim jacket cut. It’s a navy, almost conductor stripe, with navy satin collar and cuffs. It just feels nautical to me. And was a windy evening and we were having dinner by the beach and I was feeling nautical, so it fit the bill. But I think what it truly deserves is a wide leg matching white denim and maybe even a heel. I finished it off with my trusty Birkenstocks - not the most glamorous outfit, but a comfy one for a casual evening.
And a few more honorable mentions…
The headscarf styling is back! This is my mom’s vintage silk - remember when I said I wanted her vintage Hermes stash? She turned that request down, but let me sift through her other options and this one is long and skinny, making it perfect for a headband.
If there is one thing about me, it is that I am a sucker for a matching PJ set. Most of mine are jersey and flannel and not optimal for summer weather. I was helping my sister shop for a Christmas top months ago, and we found our way to the J Crew sale section. This set is exactly what I never knew I needed. I love green, I love a stripe, I love a boxer waistband detail, and I love a set. And the sale on top of the sale was the icing on the cake. Lightweight cotton isn’t your usual December purchase, but I knew I would get a ton of wear out of these once warmer weather came around.
And finally, the airport fit. I hate even the thought of possibly being cold on airplanes, so I layered on multiple options for if I felt even a hint of AC. The linen pants are back, as are the flats. And the shirt, you ask? I found it at Buffalo Exchange and thought it was vintage Planet Pizza. Once I got home, I realized it is in fact Pizza Planet, and the tag inside says Toy Story. But honestly I kind of love it and that will not stop me from wearing it.
I’m not sure why, but vacation dressing always feels special to me. Packing forces me to be intentional in the pieces I bring, although I am a self-admitted overpacker despite this. If you get a checked bag, why not use it? But I still cannot bring my entire wardrobe with me. I fall into a daily outfit routine, so vacation is a good way to reset and inspire outfits that I actually put effort into. I bought a few new pieces, but I also love wearing pieces I already have instead of buying an entire new wardrobe. This forces me to get creative. So take a second next time you go on vacation to take stock of what you already have instead of going to your favorite site’s “Resort Edit”. This ended up being way longer than I thought it would be - thanks for coming on this fun little beach jaunt with me!
I may have just ordered the hollister pants because of this post.
OK, these vacation looks are so cool. Especially love the first outfit with the linen pants and top and orange shoes!