20 Stylish & Comfy Vacation Outfits  

Planning your vacation outfits can be tricky.

You want to look stylish, but you also need to be comfortable while exploring your destination.

Below, I’ve shared 20 great vacation outfit ideas that are both stylish and super comfy.  

Related: What to Wear in London: 16 Chic Outfits

20 Comfortable and Stylish Vacation Outfits

Let’s discuss the outfit that I consider ideal when you’re going on vacation.

1- Maxi Dress with Summer Sandals

A flowy maxi dress always feels right for a vacation day. It’s light and airy and keeps you cool in warm weather. Dresses with floral or bright patterns give off happy holiday vibes.  

You can wear it with flat sandals for daytime walks or upgrade to wedge sandals for a casual dinner. This is also an excellent outfit for beachside towns or tropical destinations.  

2- High-waisted shorts with a Sleeveless Blouse

This combo is perfect for sunny holidays. High-waisted shorts are comfy and flattering, while a sleeveless blouse adds a polished touch.  

For some extra fun, go for vibrant prints or pastel colors. Finish with sneakers or slip-on flats, making it ideal for sightseeing adventures.  

3- Linen Wide-Leg Trousers and a Fitted Tank Top

Linen trousers are breathable and chic, especially in hot weather. A fitted tank top balances the look without making it too casual.  

This outfit works wonderfully when you want to feel stylish yet relaxed. You could add leather slides or comfy mules to dress it up a little.  

4- Flowy Skirt with a Cropped Tee 

I love a flowy skirt because it adds movement to your outfit while keeping it breezy. Pair it with a simple cropped tee for a trendy and comfortable look.  

It’s excellent for exploring markets or museums. Add sneakers or sandals, depending on how much walking you’re doing.  

5- Romper with Flat Espadrilles

A romper makes getting dressed super easy. Choose one with an adjustable waist for the perfect fit and comfort all day long.  

Flat espadrilles combine comfort with vacation style, making this outfit ideal for casual daytime outings or boat rides.  

6- Skinny Jeans and an Oversized Button-Up Shirt

Skinny jeans might not feel like a vacation staple, but they’re great for more fabulous destinations. The oversized button-up adds a relaxed, chic touch and keeps it comfy.  

In my experience, you should roll up the shirt sleeves for a laid-back look. Ankle boots or white trainers complete this outfit perfectly.  

7- Jumpsuit with Sneakers

A jumpsuit is trendy and effortlessly stylish. Look for one with soft fabric so it’s comfortable for a long day of exploring.  

Tie a belt around your waist for some structure and pair it with sneakers for a practical but chic vibe.  

8- Denim Shorts and a Loose Graphic T-Shirt 

Denim shorts are a classic vacation piece. Add a loose graphic tee to make the outfit feel casually cool.  

This no-fuss look is perfect for walking along the beach or grabbing coffee at a local café. Throw on some flip-flops to keep it simple.  

9- Wrap the Dress with Ballet Flats

A wrap dress looks flattering on everyone and works for so many occasions. The adjustable tie lets you control how snug or loose you want it to feel.  

According to my experience, ballet flats add a touch of sophistication and are comfortable for activities that don’t involve tons of walking.  

10- Cargo Trousers and a Lightweight Hoodie

For cooler climates or active holidays, cargo trousers are both functional and stylish. A lightweight hoodie adds warmth but doesn’t feel bulky.  

Wear hiking boots or rugged sneakers, and you’re ready to explore nature trails or city parks.  

11- Midi Skirt and an Off-Shoulder Top

A midi skirt can feel dressy but still be super comfortable. Pairing it with an off-shoulder top gives a feminine, summery vibe.  

This outfit is great for evening dinners or romantic strolls. You can finish it with heeled sandals or wedges.  

12- Culottes with a Racerback Tank

Culottes are super comfy yet trendy, with their flowy silhouette that works for almost any activity. Add a racerback tank to keep the outfit casual yet polished.  

For shoes, stick to sandals or opt for stylish flats for extra versatility when roaming through cities.  

13- T-Shirt Dress with Slip-On Sneakers

A T-shirt dress is simple and fuss-free, perfect for low-key vacation days. Look for one in a soft cotton material for maximum comfort.  

I recommend you slip on sneakers that are comfy for long walks and keep this outfit sporty and fresh.  

14- Paperbag Trousers and a Fitted Top  

Paperbag trousers are perfect for vacation chic. The high waist looks stylish, and their roomy fit keeps them comfortable.  

Adding a fitted top creates balance, and low-heeled sandals elevate the look for dinners or sightseeing.  

15- Playsuit with Gladiator Sandals

Playsuits are a fun, youthful choice. They’re easy to wear and ideal for both daytime exploring and evening events.  

Gladiator sandals add extra flair, making the look more playful and dynamic.  

16- Joggers with a Relaxed Knit Sweater

For cozy, laid-back holidays, joggers are perfect. Pair them with a relaxed knit sweater for warmth and style.  

This outfit works for flights or cooler-weather vacations. Add slip-on loafers to stay stylish yet comfortable.  

17- White Blouse and High-Rise Flare Jeans

A crisp white blouse paired with high-rise flare jeans creates a timeless and elegant look. It works well for both casual and slightly dressy settings.  

You can wear heeled boots for a 70s-inspired vibe or trainers to keep it more casual.  

18- Striped Shirt with Khaki Shorts  

Striped shirts scream holiday vibes and pair effortlessly with khaki shorts. It’s a simple, classic, and relaxed look.  

I believe you should add espadrilles or canvas shoes to give the outfit a coastal touch, perfect for beachy destinations.  

19- Maxi Skirt with a Halter Top 

A maxi skirt keeps you feeling breezy and free, while a halter top adds a summery, bold vibe.  

This outfit is excellent for tropical vacations or days spent by the water. Add beaded sandals for a bohemian feel.  

20- Lounge Set with Chunky Trainers

A matching lounge set is comfy but still looks put together. Choose neutral tones for a chic yet low-key vibe.  

Chunky trainers make this outfit perfect for travel days or casual walks around your destination.  

Conclusion

There you have it: 20 amazing outfit ideas that bring together comfort and style. Don’t be afraid to mix and match these looks to suit your personality and the type of holiday you’re planning.  

With these, you’ll not only feel great but look incredible in all your travel photos, too! Which look are you trying first?