Outfit Diary: Summer Holiday on Cape Cod
8 warm-weather looks featuring my summer hero pieces
Happy August, friends! I’m back from my annual summer holiday on Cape Cod where I spent the last two weeks indulging in coastal bliss. Picture this: sunny days (don't worry, I slathered on the SPF), mouthwatering lobster rolls, locally caught oysters, and plenty of lazy beach reading. I even managed to sneak in some well-deserved naps (the post beach, pre dinner type IYKYK). It's my favorite summer escape, and every minute there felt like a slice of heaven. I’m already dreaming about next year's trip!
I plan to publish a Cape Cod (plus Nantucket) travel guide over the next few weeks, but for now, I’m highlighting the fits and looks I wore on my summer getaway. Before we dive in, let's set the stage — don't expect a minimalist packing guide here (I'm an unabashed over-packer, still working on that). Instead, I'll show you how I transformed my everyday summer MVPs into chic summer vacay looks. These outfits feature versatile pieces that shine both on vacation and in my regular life.
The Vibe
My summer vacation style? I’d describe it as coastal grandma meets surfer nephew. Think casual-but-elevated neutrals paired with relaxed silhouettes, bold pops of color, and boho-inspired accessories. It's like Something's Gotta Give had a love child with Blue Crush — polished yet laid-back, effortless but put-together, where New England prep flirts with West Coast surf vibes.
This aesthetic aligns perfectly with my everyday San Francisco style. I'm all about modern, classic, and playful looks — classic pieces with a modern twist, and I'm not shy about playing with color, trends, and fresh styling tricks.
Instead of creating a whole new vacation persona (and blowing my budget on a fantasy wardrobe), I built my vacay looks around my tried-and-true staples. If you're tempted by vacation shopping sprees, my friend
of The Found Journal published a fantastic piece on avoiding that trap — it's a game-changer!The Looks
Now, onto the fits! In no particular order, here are the outfits I wore and my thoughts behind each look.
1. Beach ensemble
This is my go-to look for beach days. Oversized linen shirts are a top summer MVP — I throw them on as cover-ups, layer them over tees and tanks, or wear them solo with trousers, shorts, or denim. This particular linen number got so much wear during my two-week trip, I lost count (pro tip: I sized up to a M for an extra slouchy vibe).
White linen pants have been my trusty travel companions for a few years now, always making the cut for warm weather getaways. At 5'3", I'm wearing these pants in the regular length and don't mind the subtle fabric puddle at my feet. But if you're 5'4" or under and prefer a perfect hem, the petite version might be your best bet.
The accessories really kick this look up a notch. Lately, I've been all about statement chokers, pearls, and eye-catching pendants. While my trusty raffia basket usually handles beach duty, this tote stole the show. It was a thoughtful gift from Paris, and it felt like the perfect refresh for my beach gear lineup.
2. Black & white with a twist
I wore this outfit for a laid-back dinner in town. It's the perfect example of how to jazz up your everyday clothes for vacation with just a few key accessories. A basic black tank* with a white eyelet maxi skirt is something I'd easily wear for a chill afternoon in the city. But here's where the magic happens — throw on some playful beaded jewelry, slip into studded sandals, grab a statement clutch, and bam! Suddenly you've got a vacation outfit that turns heads without trying too hard.
3. Brat summer
This look is my take on brat summer. The star of this outfit? My green silk shorts — a lucky score from the hand me Doen sale. I built the whole look around this gem, letting it shine. I went with my reliable black tank as a base and topped it with my favorite Donni bubble top from last summer — still loving that baroque pearl detail.
For accessories, I kept it simple — my go-to barely-there sandals, a cool east-west basket bag I found at a local shop, and a new beaded necklace from Rooni. I’m really into anklets as well — here’s the stack I wore the entire trip.
I wore my brat outfit for afternoon drinks at Chatham Bars Inn. It was fun to see how my look stood out among all the printed nap dresses, wedge espadrilles, preppy polos, and khaki shorts.
4. Clambake chic
This outfit might be my favorite from the whole trip. I wore it to our backyard clambake, which is hands-down my favorite summer tradition. I wanted to feel comfy but still fit the vibe while running around on the grass and cracking open some tasty lobster tails.
I didn't want to look too on the nose for a New England clambake, so I went for a laid-back coastal look with a touch of tomboy. Rocking my trusty striped tee, flowy cotton skirt, and a few pops of red, I felt like I could win gold in lobster cracking!
5. (Red) pants party
Red strikes again! Donni came through with the perfect timing, sending me their effortless linen pants* just in time for my getaway. I've been a longtime fan of Donni's pants, and this breezy linen version hit all the right notes. Let's just say my love affair with their bottoms is still going strong. The linen Simple Pants boast the same comfy elastic waistband and relaxed fit as their silky version. The fabric feels soft yet substantial, and while the 30-inch inseam runs a bit long on my 5'3" frame, I'm actually digging the slouchy hem vibe. I went with my usual size (S) for that true relaxed feel, but sizing down is an option if you're after a more tailored look.
Since these pants were the star of the show, I kept the rest of the outfit low-key. I paired them with a sweet eyelet top (matching the skirt I wore with the black tank), leather flip-flops, and my new basket bag.
These pants even made the cut for my flight back to SF. I styled them with an oversized tee, cozy cardigan, and fisherman sandals*. It's official — they're joining my airport pants hall of fame alongside my other Donni favorites.
6. Coastal happy hour
I’m calling this look "Cape Cod chic". It's got that easy-breezy New England summer vibe — you know, with the gingham dress, comfy cardigan, and cute basket bag. The red carnelian necklace adds a splash of surfer nephew vibes. It's one of those outfits where I feel put together but not like I’m trying too hard.
I wore this for a fun afternoon at Chatham Bars Inn. We had some snacks and drinks, and I ended up plopping down on the grass to listen to the band. There I was, Aperol spritz in hand, just soaking up the summer day. It was perfect — comfy enough to sit in the grass but still nice enough for a fancy spot like that. Just my kind of easy summer style.
7. Nantucket best
This was my Nantucket day trip look. It was an extremely hot and sticky day, so I needed something easy and comfy that wouldn't show sweat after hours of exploring the island. This dress has been my spring and summer MVP — it’s proven to be an incredibly versatile piece, so packing it was a no-brainer.
My new basket bag has been the real star of this trip. The east-west style feels modern along with an ideal size that's neither too big nor too small for everyday wear, and it goes with pretty much any outfit. This probably won't be the last time you'll see me with this bag.
These fisherman sandals* are my new go-to’s for walking around — they're just as comfy as sneakers. I've been wearing them on all my recent trips, so I knew they'd be perfect for a day of wandering Nantucket.
I'm a big fan of throwing on a baseball cap* instead of a sun hat with feminine dresses. It keeps things casual and less "look at me, I'm on vacation." Plus, you should know by now — I had to add a pop of red!
8. Cape Cod fancy
Ok, so this was probably the "fanciest" I got on this trip. We had a special dinner at one of the restaurants in the Wequasset resort — it was a belated birthday celebration for my partner, with his parents joining us. Fancy, but still Cape Cod, you know?
The weather threw us a curveball that day — chilly and rainy. I’m glad I tossed this shirt in my suitcase at the last minute. It was the perfect layer to throw over this silk maxi dress — it also added a laid-back vibe to my look. The dress is an old Toteme number (here’s a nice alt) that I scored on major sale last summer and she's been a real keeper.
Now, let me tell you — I have a strict "no heels" policy for summer Cape trips. They just don’t vibe with the casual, low key feel of Cape Cod. I went with these studded sandals — comfy yet adds an interesting twist for a nice dinner. I threw in a fun clutch to jazz it up a bit, but kept it pretty chill overall.
There’s always that tricky balance of dressing up for a nice restaurant but still feeling like you're on a laid-back summer vacation. I think this outfit nailed it — polished enough for a fancy resort dinner, but still totally Cape Cod casual. Plus, I didn't freeze in the unexpected chill, so that's a win in my book!
What’s your favorite look from my Cape Cod trip? I’d love to know in the comments!
Until next time,
Angela
*Items marked* were generously gifted by brand partners. This post also includes some affiliate links. I may earn a small commission if you make a purchase through one of the links above - at no extra cost to you. As always, I only include links for products I own and love or would buy for myself.
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Love it all. Chatham Bars Inn is a long time client of mine— so special up there and your looks are 💯✨
Such a fun trip!! 🦞🌊 I’m here for the brat summer look!