Guest Post: 15 Casual Outfits Perfect for Weekend Getaways

Happy Friday and Hello, August! To kick off this month and all the travel I have planned throughout the weeks ahead, I wanted to turn ‘Coffee & Chiffon‘ over to Suzy Walsh for today’s post!

Suzy is a celebrated fashion blogger whose style insight and eye for trends has spanned over a decade. Today, she’s providing some ideas and tips for the “Weekend Warriors” like myself – who need to pack an overnight bag with enough clothes to get them through a couple days by the coast, on the lake, or visiting friends/family in the city.

Take it away, Suzy!

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Weekends promise freedom. They offer a short escape from routine, a change of pace. Be it a quick coastal drive, a city break, or a countryside stay, packing light without compromising style is essential. The challenge lies in curating outfits that feel effortless, travel well, and look even better in photographs.

Each piece listed below strikes a balance between comfort, utility, and effortless elegance.

No overthinking. No overpacking.

Just sharp weekend style, ready for wherever the road leads.

1. Linen Shirt Dress

Lightweight and breathable, the linen shirt dress transitions easily from brunch to beach. Its structure offers a tailored look, while the fabric moves with the breeze. Pair with minimal slides and a tote.

It folds flat, resists wrinkles, and feels cool in warm weather. A go-to piece when time and space are limited. Belt it for a tailored fit or wear it loose for added comfort. Easy to dress up or down.

2. Slip Dress + Denim Jacket

Elegant without effort. A neutral-toned slip dress under a well-fitted denim jacket strikes the right balance. This pairing flatters most body types and packs flat in your weekender.

The contrast of soft silk and structured denim adds visual interest. It moves easily from day to night with a quick change of accessories. Hang the dress on wooden coat hangers to preserve its shape and fabric between wears.

3. Classic White Tee + High-Waisted Jeans

Timeless and functional, this duo handles everything from road trips to rooftop drinks. Opt for straight-leg jeans and a quality tee with weight. Add a leather belt and ankle boots to sharpen the edge.

It works across seasons and settings. Layer with a blazer or wrap a sweater around your shoulders. This pairing stays relaxed but always looks intentional.

4. Knit Co-Ord Set

A matching tank and midi skirt in soft knit fabric blends polish with comfort. Ideal for city strolls or gallery visits. Style it with sneakers or delicate sandals, depending on the pace of your day.

It packs easily and resists creases, making it a practical pick for short stays. Add a lightweight jacket for cooler evenings or wear each piece separately to stretch your wardrobe further.

5. Lightweight Jumpsuit

The jumpsuit is a one-piece solution for stylish dressing. Look for one with a drawstring waist or subtle tailoring. It travels well, resists wrinkles, and moves seamlessly from day to night.

It saves space in your bag and simplifies decision-making. Add sandals and a crossbody bag for daytime, then switch to heels and earrings for dinner.

β€œI wore it twice without thinking. It made packing simple,” said Chloe Bennett, after a weekend in Santa Barbara.

6. Oversized Button-Down + Biker Shorts

Borrowed-from-the-boys meets off-duty model. This combo is functional and stylish. Tuck, tie, or let the shirt hang loose over mid-thigh shorts. Finish with chunky sneakers and sunglasses.

It works for coffee runs, boardwalk strolls, or long drives. The look feels put-together without trying too hard. Add a crossbody bag and hoops to pull it into weekend-ready territory. It does casual right.

7. Cropped Blouse + Wide-Leg Trousers

Flattering and airy, wide-leg pants paired with a cropped blouse create a sense of elongation and ease. This set plays well in countryside cafΓ©s or open-air museums. Add espadrilles for lift without strain.

The look strikes a balance between volume and proportion, making it ideal for relaxed settings with a touch of polish. A crossbody bag and sunglasses complete the outfit without crowding it.

β€œI wore this combo all afternoon in the vineyard and still felt polished at dinner,” said Erin Lopez, who recently toured the Barossa Valley.

8. Cotton Midi Dress

Structured yet casual, the cotton midi is a summer staple. It holds shape, travels well, and fits into nearly any getaway plan. Cinch with a belt or keep it minimal.

Easily from day outings to dinner plans. It stays cool, needs no fuss, and works with any shoes. Layers well with a denim jacket. And it always looks intentional without trying too hard.

9. Tank Top + Paperbag Shorts

A tank made of ribbed cotton or linen tucked into high-waisted paperbag shorts offers both structure and breathability. Ideal for humid destinations. Add strappy sandals or sleek slides.

Crisp lines at the waist elevate the casual tone. The pairing feels relaxed yet intentional, making it easy to move in and flattering from every angle. Wear it for market strolls or cafΓ© stops.

Packs light and works without a second thought.

10. Lightweight Blazer + Tailored Shorts

Upgrade the weekend look with a soft blazer layered over a camisole and tailored shorts. It reads polished but remains relaxed, perfect for winery visits or rooftop brunches.

The contrast between structure and ease keeps the outfit balanced. Add loafers or low block heels for a clean finish. Works well from midday plans to evening reservations.

11. Long Sleeve Romper

A romper with long sleeves provides coverage while keeping you cool. Choose neutral tones for versatility. Pair with low-top sneakers or ankle boots depending on the terrain.

Soft fabrics and clean lines create balance between comfort and structure. Easy to slip on, it simplifies mornings and keeps your look cohesive. Add a belt bag or sunglasses and head out.

12. Maxi Skirt + Fitted Tee

The soft drape of a maxi skirt anchors the slim silhouette of a fitted tee. This combination offers movement and ease. It works for travel days or evening walks.

Comfort meets quiet polish in this pairing. Add a crossbody bag and slip-ons for long hours on the go. Simple, unfussy, and always photo-ready.

β€œI wore this on the train and straight to dinner. It felt like a uniform, but in the best way,” said Leila Monroe, after a weekend in Lisbon.

13. Hoodie + Leggings (Upgraded Version)

Think clean lines and raised materials. A neutral-toned hoodie with black or navy leggings delivers comfort without looking sloppy. Add gold hoops or a sleek crossbody to upgrade.

This look handles long drives, airport waits, and quick stops with equal ease. Soft layers offer warmth without bulk, and polished accessories keep it pulled together.

14. Knit Polo + Linen Pants

A knit polo adds subtle sophistication, while linen pants maintain a relaxed feel. This pairing travels well and works for coastal towns or al fresco dining.

The textures strike a balance between polish and ease without feeling overdone. Soft structure keeps the look fresh from morning to evening. Ideal for warm breezes and unhurried plans.

β€œI wore this to a vineyard lunch and felt perfectly dressed all day,” said Elena Marks, after a weekend along the Amalfi Coast.

15. Cropped Jacket + Midi Slip Skirt

A cropped utility or bomber jacket layered over a midi slip skirt adds structure to fluidity. It’s a modern blend that handles shifts in weather and occasion.

The jacket adds edge while the skirt keeps things soft. Together, they create a balance that is bright enough for dinner and casual enough for daytime. Add boots or sneakers depending on the plan.

It works in transit, in town or anywhere in between.

β€œI flew in wearing it and went straight to dinner,” said Nina Clarke after a weekend in Austin.

Wrap Things Up!

Weekend getaways are too short for bad outfits. These options pack easily, mix and match well, and help you feel pulled together with minimal effort. Each outfit leans on timeless shapes, thoughtful materials, and simple enhancements. Chosen with intention, casual dressing has impact. It becomes an integral part of the destination.

Style becomes memory what you wear shapes how you feel in the moment and how you will remember it later.

[ Author – Suzy Walsh is a renowned fashion expert and blogger who has contributed to several fashion websites and blogs as a guest author. With her vast knowledge and experience in the fashion industry, she has become an authority on fashion trends and sustainable fashion. ]

IMAGE CREDITS: jesskeys.com,Β brightontheday.com,Β brooklynblonde.com,Β sowears.net,Β naturallife.com,Β tobebright.com,Β alexandralapp.com,Β waywardblog.com,Β busbeestyle.com,Β mckenziegillespie.com,Β laurenschwaiger.com,Β themotherchic.com,Β tiaperciballi.com,Β memorandum.com, andΒ cherylshops.net

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I want to again thank Suzy for such a great guide! So many of these outfits are perfect for these last weeks of Summer and as we slowly but surely begin to transition into Fall-wear again. I’m looking forward to packing some of these essentials and combinations when I head to the Cape and Newport for a couple of weekends away this month!

Here’s wishing you all a beautiful beginning to your August and a fabulous (and fashionable!) weekend ahead!

xo

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Hi! I'm Ashley. I'm a legal specialist, a blogger and a radio personality with a makeup and shoe addiction based out of Boston and the Pioneer Valley. These are my (mis)adventures.

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