Stay Stylish On Vacation


We love vacation, but who wants to look like a tourist? Do you really want to be the one walking around Times Square in baggy sweats and a tee-shirt with your hometown college football team mascot? Vacation is more than just a time to sightsee – it’s an opportunity to wear something you wouldn’t normally wear back home. It’s a chance to dress up for a Broadway show, to wear something flashy to a trendy club, and your opportunity to really go all-out in combining comfort with fashion.

Our favorite personal stylist, Devoreaux Walton from The Modern Lady, agrees that vacations “are a way to shake up life and escape from the regular day-to-day.” Devoreaux tells us “ When on vacation, I suggest packing one outfit for day and one outfit for night. Each outfit can be casual or dressy, based on your trip’s itinerary. T-shirts, chinos, skirts, cotton dresses, shirt dresses and dark wash denim jeans are all great options for sight-seeing and exploring a new town. Lounge and athletic attire is best to save for participating in a sport or outdoor activity. I recommend always packing at least one item of outerwear, for example a sweater or jacket, even in the summer months, because of possible cooler evenings, mornings and air conditioned environments.”

Tonia Ryan, celebrity stylist from, has some first-rate advice, and you don’t even need to be a celebrity. According to Tonia, your vacation wardrobe really depends on what you want to do on vacation: “Some clients simply want to go on vacation and relax. They don’t want to have to think about what to wear and that is where I come in. Even if you want to be comfortable, I can still make you look fashionable with minimal effort.”

That still means avoiding the sweatpants and Fightin’ Irish tee-shirt, which will tell all the hucksters in Times Square that yes, you are a tourist. Tonia’s advice on casual ranges from a cool bodysuit with baggy boyfriend-cut jeans, or a long, flowy maxi-dress with a matching cardigan.

Going to a Broadway show? Fashion on opening night ranges from high formal to street chic, but everyone has a style they want to show off when they’re going to see “Phantom.” Tonia says “This is where you finally get the chance to dress up and show off, so go for it! Wear a bold gown or the elegant dress you have always wanted to wear.”

The ladies over at Tobi tell me that “When packing for vacation, it’s no secret everyone wants to go beyond the typical ‘tourist attire.’ If you dare to differ it’s essential to pack unique pieces that capture your individuality.”

Tobi has a useful set of “do and don’t” guidelines:


  • Bring an all-purpose LBD. Dress it down for a casual day, or play it up with some statement jewelry for a night on Broadway. 
  • Pack a day-to-night bag. Space in your luggage is limited, so get yourself something that can do both. Pro-tip: a black studded bag will add interest and texture to take your look from day-to-night. 
  • Layer your look. Stick to simple colors and patterns that layer easily. Choose thin knits to lighten your suitcase load. For warmer weather and activities, pair your look down. When it gets cooler, mix in a blazer, some tights or a coat. 


  • Overdress. You want to be comfortable since you’ll be exploring your vacation destination, so you need to make sure your pick is easy to move in. 
  • Be afraid to wear something twice. The pieces you choose to pack will be doing double-duty. Swap in understated or dressier blouses to change up the look of your core outfit.

We’re especially loving Tobi’s “Another Dimension” black shift dress.

Amanda Hudes, whose event planning company Smiling Through Chaos helps women look and feel their best, has a standard go-to package to suit every travel occasion. Amanda shared her travel list with The Vivant:

  • always a bathing suit
  • one or two lightweight dresses with one cardigan and one jacket to go with
  • one pair of cropped or frayed jeans and one pair of lightweight or slim fit pants with a few different tops of various lengths and sleeve types to go with 
  • practical shoes for walking, one pair of heels, and a sandal of some sort for walking around in the hotel room (ooh those gross floors!) and outside if it’s beautiful weather
  • one or two cute hats to “make” the outfit
  • at least two statement necklaces to add that “vroom” to a basic pairing

Knowing what to wear on vacation may be important, but of equal importance is having something stylish and practical to store it all. The Birdie Gym Bag from Jemma Bag, designed by Joanna Lau, is a chic looking travel bag with a ventilated compartment for stowing shoes, and interior pockets for daily essentials, including a laptop and water bottle. It also comes with an additional cosmetic case and laundry bag!

And while you’re at it, every traveler needs to be prepared for poor weather, but there is the ever-present challenge of trying to fit rain gear into your already-crowded suitcase, so you will want to find a good packable rain jacket which is easy to fold, yet eminently stylish at the same time. 

We’re also loving Hark+Hammer, which blends classic minimalism with edgy silk prints. Their kimono top is perfect for layering with other prints, over an LBD or black pants or leggings. The printed silk charmeuse design has an open front, making it perfect for layering, and the loose fit is emphasized by wide cropped sleeves.

One of our favorite New York City travel and fashion blogs is Sher She Goes, and Sher always has some great ideas for fashion and travel. She says her two must-haves for travel are maxi-dresses and joggers. Sher tells The Vivant that “For stylish travel, I love bringing a comfortable, versatile maxi dress. Because of the longer length, maxi dresses instantly make your outfit look more formal and as a bonus, they’re perfect for conservative countries or entering religious monuments or temples. I look for colorful maxi dresses that are form fitting in the torso with a loose skirt, so they’re stylish but still quite comfortable to walk and wear all day.” For when comfort is a priority, Sher says, “For the airport, I prefer to stay comfortable while still looking put together and highly recommend jogger pants. They’re usually made of comfortable “sweats” like material but the tapered legs and high waisted nature of joggers make them look much more classy. Add a simple t shirt and a leather jacket and you’re ready to tackle the security line in style!”