There is nothing quite like the rush of packing a suitcase, printing your boarding pass, and heading out for a summer getaway. Whether you’re managing airport logistics with kids, taking a long-awaited office break, or jetting off to a coastal resort, looking put-together while traveling is easier than you think.
You can absolutely stay comfortable through a long flight, road trip, or sightseeing tour while still looking effortlessly classy. Here are three fool-proof, timeless outfit formulas that will take you from the terminal to a resort dinner with total ease.
The plane: Elevated comfort
The secret to terminal style is breathable fabrics, relaxed silhouettes, and strategic layers. Airplanes are notoriously unpredictable temperature-wise, so a great "third piece" is essential.
The bottoms: Swap the fleece joggers for a pair of wide-leg linen or lightweight cotton trousers with a comfortable elastic waistband. Alternatively, a pair of relaxed, wide-leg denim with some stretch, or a ribbed sweater knit midi skirt works beautifully.
The tops: Pair your bottoms with a short-sleeve knit sweater-tee or mock-neck tank, a classic button-down shirt, or comfy blouse.
The miracle layer: Finish the look with a structured denim jacket, an oversized linen blazer, or a lightweight knit cardigan draped over your shoulders. It keeps you warm against the airplane AC and adds instant structure.
Footwear: Classic white leather sneakers, supportive loafers, or closed-toe ballet flats keep your feet happy during long walks to the gate while looking polished.
The sightseeing day: Effortless movement
Exploring a new town, checking out local shops, or walking along the shoreline requires a look that allows for maximum movement without sacrificing a clean, classic aesthetic. Again, think breathable and functional.
The one-and-done options: A classic, button-down shirtdress in cotton, poplin, or linen is a fantastic option. A cotton midi or maxi dress (pastels, florals, or eyelet), a knit romper, or a breezy linen jumpsuit offers that same effortless, pulled-together feel. If you want a touch more structure, try adding a raffia or leather belt.
The separates mix: If you prefer separates, pair a flowy midi skirt (A-line or slip style) with a simple tucked-in knit tee. Style high-waisted linen or tailored cotton shorts or gauze pants with a crisp, rolled-sleeve poplin button-down or light sweater for a casual look.
The accessories: Protect yourself from the sun with a classic straw fedora or a pair of vintage-inspired sunglasses like cat-eye or aviator styles. A leather crossbody bag or a lightweight straw tote keeps your hands free for taking photos or holding a gelato.
Footwear: Opt for supportive walking sandals with secure straps (leather, espadrilles), stylish slip-on canvas shoes, or your most comfortable loafers or flats.
The dinner: Classic elegance
Vacation dinners are the perfect time to lean into a slightly more romantic, timeless aesthetic, perhaps with a touch of Old Hollywood resort style.
The dress options: Choose a high-neck, boat-neck, or wrap midi or maxi dress in a breathable cotton poplin, satin, or linen. Solid jewel tones, crisp white or neutrals, or subtle, classic patterns like stripes or delicate florals work beautifully.
The separates alternative: Style a pair of elegant wide-leg cream trousers with a sleeveless knit halter top or a silk blouse. A monochromatic look – like a matching linen top and pant set – instantly looks expensive and chic.
The accessories: Tie a vintage silk scarf around your neck, into your ponytail, or onto the handle of your handbag for an instant injection of classic charm. Simple jewelry like pearls or delicate gold, and a padded headband or sparkly hair clip add instant elegance.
Footwear: A low, block-heeled leather sandal, a sophisticated espadrille wedge, or a polished flat slide offers the perfect touch of elegance while remaining practical for walking along cobblestone streets or boardwalks.
The ultimate versatility blueprint
If you want to pack light but have endless outfit options, stick to this fool-proof blueprint for maximum mix-and-match potential:
The colors and prints: Build your base with white, cream, navy, olive, or tan, then toss in soft summer pastels like powder blue, sage green, lavender, or blush pink. Add texture with classic floral prints, delicate toile, or timeless stripes.
The only three shoes you need: Pack one pair of classic white sneakers or slip ons for transit, supportive leather walking sandals for daytime exploring, and a metallic slide or sophisticated espadrille wedge for dinner.
The capsule mindset
Vacation fashion should be fun, simple, and beautifully you. By packing a few smart formulas that make you feel confident and comfortable, you can spend less time staring into your suitcase and more time making memories. Here’s to traveling in style!