5 Stylish Outfits for Weekend Getaways

Planning a weekend getaway? Whether you’re heading to a beach town, mountain retreat, or a spontaneous city escape, your style shouldn’t take a vacation. At Wessi, we believe every trip is an opportunity to showcase your fashion sense. That’s why we’ve curated five stylish outfit ideas to help you travel light while staying effortlessly sharp.

1. Smart Casual Combo for City Explorations

If your weekend plans involve museums, cafes, or strolling through charming streets, aim for a refined but comfortable look. Pair slim-fit chinos with a lightweight shirt in a neutral tone. Layer with a well-fitted blazer to elevate the outfit.

Wessi Tip: Choose a patterned blazer or one in a seasonal color like olive or light grey. It adds personality without overdoing it.

Complete the look: White sneakers and a leather-strapped watch.

2. Relaxed Elegance for Countryside Retreats

For rural getaways filled with nature, wineries, or peaceful cabin stays, think relaxed but tailored. Go for stretch denim jeans, a soft knit t-shirt, and a casual jacket or cardigan.

Wessi Recommends: A cotton bomber jacket or a casual textured blazer from Wessi’s weekend collection. They keep you warm in the evening breeze and stylish all day long.

Complete the look: Suede loafers or desert boots for an elevated rustic vibe.

3. Beach-Ready Yet Polished

Even if you're dressing down for the beach, you can still look polished. Swap out basic tank tops for a linen short-sleeve shirt and chino shorts. Keep the palette bright and breezy — think pastels or white with tan.

Wessi Style Tip: A half-buttoned printed linen shirt from Wessi adds a touch of coastal elegance while keeping things cool.

Complete the look: Espadrilles or leather sandals and a pair of sleek sunglasses.

4. Evening Dinner Look

Weekend getaways often include a nice dinner out. Pack one elevated outfit that transitions well from day to night. A dark pair of slim trousers, a crisp shirt, and a blazer make the perfect trio.

Why Wessi? Our collection of smart-casual blazers and tailored shirts ensures you're ready for any last-minute dinner reservation or rooftop drink.

Complete the look: Derby shoes and a pocket square if you want a bit of flair.

5. Airport-Ready and On the Go

Comfort and style can co-exist — especially on travel days. Opt for jogger-style trousers or stretch chinos, paired with a plain white tee and a lightweight jacket. Layers are your best friend on planes, trains, or long drives.

Wessi Suggests: A stylish zip-up jacket or minimalist blazer to maintain a sharp silhouette without sacrificing comfort.

Complete the look: Slip-on shoes or low-top sneakers for easy transitions through security lines and city sidewalks.

Final Tips for Packing Light and Right

• Stick to a cohesive color palette. Neutral tones like navy, beige, and olive allow for easy mixing and matching.

• Choose multi-functional pieces. A Wessi blazer, for example, can work for both a day exploring and an elegant dinner.

• Focus on fit. Regardless of how casual or formal the look is, well-fitting clothes always look better.

With the right wardrobe, every weekend getaway becomes a chance to express your personal style. At Wessi, we design menswear that balances elegance, comfort, and functionality — so you always travel in style.