Pinterest-Perfect Summer Vacation Looks for the Beach, the Boardwalk & Beyond

By Princewill Hillary

Planning a summer vacation gets me thinking about two things: where I’m going and what I’m wearing.

Whether I’m island-hopping in Greece, wandering through coastal towns, or relaxing on a cruise, I want my suitcase packed with outfits that photograph well and feel effortless.

The right pieces make every moment easier. Here’s what every summer travel bag needs. Here’s what I bring every time.

Linen Button-Up That Smells Like Sunscreen

Linen Button-Up That Smells Like Sunscreen

An oversized linen shirt works over a swimsuit at the beach, tucked into denim shorts for lunch, or worn open with a crop top and loose pants. The fabric breathes in humidity and actually looks better wrinkled.

This piece has proven itself in Positano and Miami and fits anywhere the sun shines. Pack one in a neutral tone like white, sand, or pale blue for maximum versatility.

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Oversized Straw Hat with Main Character Energy

Oversized Straw Hat with Main Character Energy

A wide-brimmed straw hat transforms a basic outfit into something memorable. Pair it with long skirts, swimsuits, sandals, whatever the day calls for.

It protects the face during midday heat and creates a strong silhouette in photos. This hat has traveled to Santorini and Hawaii and remains the one item nearly every seasoned traveler packs for vacation.

Seafoam Sarong for Barefoot Ice Cream Runs

Seafoam Sarong for Barefoot Ice Cream Runs

A lightweight sarong deserves a spot in every beach bag. Seafoam green is a color that feels right near water, but any soft shade works.

Wrap it around the waist or drape it over the shoulders when extra coverage is needed, walking into a café, sandy feet and all. It takes up almost no space in a suitcase but adds polish to any beach look.

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Retro Sunglasses for Polaroid-Worthy Moments

Retro Sunglasses for Polaroid-Worthy Moments

Never underestimate good sunglasses. Look for cat-eye frames, tinted lenses, or chunky vintage shapes. They instantly upgrade simple outfits and work whether the style leans relaxed and bohemian or sleek and minimal.

Retro sunglasses pull a look together and create the feeling of being the subject of a film, which is especially helpful in Europe.

Woven Beach Tote That Holds Secrets and Snacks

Woven Beach Tote That Holds Secrets and Snacks

Those photos of stylish women carrying oversized woven totes with windblown hair capture exactly the right energy. A quality tote fits a book, snacks, sunscreen, sunglasses, and a spare outfit.

It completes every vacation look, from tropical destinations to quieter coastal escapes. A good tote makes everything feel more intentional and thought-out.

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Coastal Grandma Cardigan for Windy Sunset Walks

Coastal Grandma Cardigan for Windy Sunset Walks

A soft cream cardigan with relaxed coastal vibes belongs in every suitcase year-round. When the breeze picks up after sunset, throw it over a sundress or wrap it around the shoulders.

It works for nicer dinners and gives off that breezy European elegance. Think Hamptons but less formal, more approachable, and warm.

Saltwater-Stiffened Denim Shorts with Frayed Edges

Saltwater-Stiffened Denim Shorts with Frayed Edges

The same denim shorts can last for years. Every beach trip fades them a little more, and the saltwater softens the fabric into something perfectly broken in.

Wear them with bikini tops, oversized shirts, or a bright crop top. They’re simple, versatile, and never look out of place, no matter where the trip leads.

Beaded Friendship Bracelets Made by the Bonfire

Beaded Friendship Bracelets Made by the Bonfire

Stack colorful beaded bracelets for a small pop of personality. Whether handmade or picked up at a market, they add a playful touch without overwhelming an outfit.

They recall summer camp but feel grown up when styled right. They work best with beach looks that lean casual and lived in, bringing just enough color to matter.

Rope Sandals That Belong in a Beachcore Moodboard

Rope Sandals That Belong in a Beachcore Moodboard

Rope sandals belong on every Mediterranean itinerary. They’re quirky but practical, the kind of shoe that deserves a spot on any beach mood board. Wear them with linen skirts, breezy pants, or long sundresses.

They’re comfortable enough for exploring cobblestone streets and stylish enough to count as a real fashion choice.

Mood Ring That Changes with the Tide

Mood Ring That Changes with the Tide

Rope sandals belong on every Mediterranean itinerary. They’re quirky but practical, the kind of shoe that deserves a spot on any beach mood board.

Wear them with linen skirts, breezy pants, or long sundresses. They’re comfortable enough for exploring cobblestone streets and stylish enough to count as a real fashion choice.

Platform Espadrilles for That Boardwalk Glow-Up

Platform Espadrilles for That Boardwalk Glow-Up

When a little height is needed without discomfort, reach for espadrilles. The platform lifts without sacrificing comfort, and the woven sole still feels casual and appropriate for beach settings.

Pair them with sundresses, linen jumpsuits, or jeans for dinner near the water. They’re the easiest way to look polished without trying too hard or overdoing it.

Beachy Button Pins for Your Thrifted Canvas Tote

Beachy Button Pins for Your Thrifted Canvas Tote

Personalize a canvas tote with enamel pins, especially ones with beach themes or summer sayings. They start conversations and turn a plain bag into something that tells a story.

Collect them at markets while traveling for an evolving collection. Each one marks a place visited, a moment remembered, a trip completed.

Scalloped Swimsuit That Screams Soft Girl Summer

A scalloped-edge swimsuit serves as the foundation for every trip. It’s sweet and flirty, but still functional enough for actual swimming and wave-chasing. Layer it under a gauzy shirt or pair it with linen pants for a resort look.

Whether headed to Hawaii or lounging poolside, a swimsuit like this earns its spot in the suitcase every single time.

Shell Anklet with Subtle Summer Camp Nostalgia

A shell anklet is a small detail that adds character to any beach outfit. Wear it barefoot in the sand or with rope sandals and a loose dress. It’s subtle but brings back memories of carefree summers and simpler times.

It’s the kind of accessory that makes a look feel authentic instead of staged or overly planned.

Breezy Eyelet Dress for Golden Hour Gelato

Golden hour calls for a soft eyelet dress in white or pastel. It’s feminine, breathable, and perfect for impromptu gelato runs or seaside dinners.

Pack one for every beach vacation or European boardwalk trip without question. It’s timeless and pairs beautifully with a straw bag, minimal makeup, and nothing more.

Citrus-Colored Crop Top for That Y2K Energy

A bright crop top in orange, lemon, or lime brings immediate energy. Those shades make a tan look deeper and bring life to the whole outfit.

Wear it with high-waisted shorts or over a bikini for beach days. It’s a punchy addition that makes everything feel more summer and infinitely more photogenic.

Crochet Cover-Up That Says “I Made This”

There’s something special about a crochet piece that looks handmade. A vintage cover-up from a flea market adds texture and charm to every vacation outfit.

Whether somewhere tropical or just wanting that handcrafted feel, crochet works universally. Look for pieces with interesting patterns or unique stitching that stand out from mass-produced alternatives.

Rattan Crossbody Bag for Flea Market Treasure Hunts

A small rattan crossbody is lightweight and unmistakably beachy. It works with Greek island looks and bohemian vacation outfits alike without forcing either direction.

It fits a phone, lip balm, sunglasses, and a few euros for market finds. It’s the kind of accessory that elevates a simple look and feels like part of the story, especially with sundresses and sandals.

Cloud-Soft Bucket Hat for Hair Wash Day Skips

A bucket hat saves the day when hair won’t cooperate. It’s soft, collapsible, and adds a casual, trendy feel to any combination.

Wear it with a swimsuit and cover-up or with wide-leg pants for something more polished. It’s attractive enough to show up in every photo without taking over the frame or stealing focus.

Striped Button Dress That Belongs in a Wes Anderson Film

A pastel-striped button-up dress with old-school charm creates instant film-quality aesthetics. Wear it with sneakers and a scarf in the hair, or swap in espadrilles for evenings.

It’s polished but playful, balancing both moods without feeling forced. Perfect for wandering old towns with something cold in hand and nowhere urgent to be.

Sunset-Hued Kimono for Late-Night Fire Pit Vibes

A lightweight kimono in burnt orange or dusty pink serves as the ideal layering piece for nighttime. Whether sitting by a fire, lounging on a balcony, or heading to dinner, it wraps up the look with ease.

It’s breezy enough for warm nights and adds a touch of flow to every outfit it touches. Choose a fabric that drapes well and doesn’t wrinkle easily when packed in a suitcase.

Tie-Dye Tee Straight Out of a Camp Core Aesthetic

This shirt brings instant nostalgia for friendship bracelets and canoe races. Pack one every summer because it adds a relaxed vibe that’s hard to replicate otherwise.

Knot it at the waist, layer it over a slip dress, or pair it with denim for a throwback moment. It’s youthful energy styled for adults who remember those summers fondly.

Nautical Knit Tank You’d Wear on a Sailboat Date

Navy and white stripes, gold buttons, crisp fabric. A nautical tank brings understated elegance to cruise outfits and beach town walks.

Wear it with tailored shorts or linen trousers for maximum versatility. It works from morning to night and never feels overdone or trying too hard to impress.

Star-Shaped Sunnies That Channel Tween-Summer Nostalgia

Star-shaped sunglasses are admittedly kitschy, and that’s exactly the point. They recall summers filled with popsicles, sleepovers, and all the joy that came with them.

Wear them without apology, especially when channeling playful energy matters more than being taken seriously. Sometimes the best vacation style is the kind that doesn’t take itself seriously at all.

Author: Princewill Hillary

Expertise: Camping, Cars, Football, Chess, Running, Hiking

Hillary is a travel and automotive journalist. With a background in covering the global EV market, he brings a unique perspective to road-tripping, helping readers understand how new car tech can spice up their next camping escape. When he isn't analyzing the latest vehicle trends or planning his next hike, you can find him running, playing chess, or watching Liverpool lose yet another game.