How a celebrity stylist would pack my bag for a 5-day trip

Much to my disbelief, and sadness, summer is nearly over. But I still have one holiday to look forward to: a five-day getaway in Spain with my family in August.

I'm expecting to spend time by the pool and the beach, eat nice dinners, and generally just have a laid-back break in the sun.

The only part that I'm not looking forward to is the packing. It's just not my strong suit. So to prepare, I spoke with celebrity stylist Tara Swennen. Her job consists of working with A-list clientele and traveling with them around the world. If anyone has some lifelong tricks to make packing easier, it's someone who manages clothing for a living.

Fresh from attending the Dolce & Gabanna show in Italy, the Los Angeles-based stylist said her job makes her an expert in packing for travel.

"I'm an avid world traveler, and my job takes me to a lot of these fun and luxurious places," Swennen, 42, said. "Not only do I pack myself, but I pack my clients."

Those clients include Kristen Stewart, Matthew McConaughey, Allison Janney, and Sarah Michelle Gellar, she added.

Swennen's first tip is to take the time to pack.

"You don't want is to be in an emergency when you get there," Swennen said of possibly forgetting a necessity. "The easiest way to do it is to put everything out on your bed, so you have a good visual of what you want to take."

I'd actually done this for the upcoming trip, so the tip made me feel good. I organized each pile into types of clothes — shirts with shirts, dresses with dresses, and sports pants with sports pants — of which Swennen approved.

Something I didn't think to include, but Swennen swears by, is a luggage tracking device.

Business Insider's Kate Duffy reported that lost baggage claims have shot up 30% amid travel chaos in the summer months of 2022, compared with pre-pandemic times. Given how chaotic air travel has been, Swennen said it is especially worth investing in something like an Apple AirTag, which costs $29 for a single pack, to avoid any stress of lost baggage.

She said she always tells her clients to not pack their valuables in a suitcase that will be checked by the airline.

"Never pack your jewelry or your favorite pieces in your luggage," she said. "If you can avoid it, don't do it."

For dinners out, I plan to bring a few dresses, and Swennen had a brilliant idea: add a blazer. It will not only ward against possibly evening chill but it immediately dresses up the look.

"Bring some type of blazer, whether it's black, tan, olive, navy, just to dress something up and obviously keep you warm," she said.

Temperatures in the evening in Barcelona can be slightly cooler in August, so I definitely want to take Swennen's advice. Also, I hadn't considered that most restaurants would have air conditioning, which can make eating indoors chilly too.

Swennan approved of my shoe options: an athetic sneaker, Converse sneakers, and a pair of sandals. I momentarily felt quite confident about my packing skills.

However, since we discussed my evening attire, she recommended I bring one additional shoe: a dressier option to go with the nighttime looks.

"[Bring] a heel to pair with your dresses," Swennan said, noting in summer that a heeled sandal is the typical go-to shoe. "If you were going to a colder climate, you could do a bootie or a pump."

When asked what items of clothing she always brings with her no matter the temperature, occasion, or activity planned, Swennen said "a good amount of neutrals" and, of course, a "great blue jean."

Her reasoning is that these pieces are so versatile that they can be worn easily throughout any trip without much styling effort. You can also mix and match.

So my hesitation about bringing a pair of jeans on a trip that is largely going to involve swimming was put to bed.

Swennen also approved of my selection of simple, neutral-hued tank tops. She said packing these items leaves space to shop for more colorful pieces while on vacation.

Swennen, who has a partnership with Affirm, said she loves to populate her closet with clothes that she finds during her travels.

"I'm a stylist, so I'm a sucker for shopping," she said. "Whatever you buy has a story. It's something you can always look on when you come home: 'I remember that trip to wherever.'"

Packing the basics, such as the tank tops and cream-colored crop top, means anything new you buy will likely match.

"The whites [and] tans — you can shop for just about anything to match with them if you want to," Swennen said.

I workout pretty consistently, for my physical and mental health, so I plan to bring workout outfits. However, I don't think I'm alone when it comes to struggling to follow through on actually exercising on holiday.

Swennen told me to adding these to suitcase would help me manifest it happening, but said not to be hard on myself if it doesn't.

"Put the idea there," Swennen said. "But if you only get around to working out once, don't beat yourself over the head."

She said that workout clothing is lightweight, which means it really doesn't take up too much space to add to the bag. But she recommends to not to go overboard.

"Most people know that they'll get to it maybe a quarter of the time," she said.

For the five-day trip, I planned to bring seven pieces of underwear, four bras, and six pairs of socks. I was conscious while packing to include more underwear than I normally use, but not go overboard. I hoped Swennen would think it was reasonable.

To my surprise, she said that overpacking undergarments is one area where it is totally fine to do.

Issues with over-packing usually come from other categories, she said.

"It tends to be one extra blazer or one extra dress where you think, 'Oh, what if I add one dinner on,'" Swennen said. "Those are actually the pieces that never tend to get worn."

I've heard about folding or rolling clothes in a specific way when packing, but I've never tried it. When I pack, I usually add clothes the way they are folded in my closet. Or, I try to lay them down in the flattest way possible.

Swennen said it may be time for me to give new methods a go.

"Find bundling techniques that work for you," she said, adding that folding and rolling are her go-to ways of packing clothes into a suitcase.

"You should fold clothes and items that wrinkle, like cotton button-down shirts or linens," she said. "Rolling is another wonderful technique to save space because it maximizes the space."

She recommends packing bulkier, heavier items at the base of the suitcase and fill from there – something that I did not do when packing my suitcase.

So how about packing on the way home? Swennen says use the same methods when repacking the suitcase before your return travels, but also consider bringing small bags to separate different dirty items for the laundry at home.

And though she follows these guidelines, she admits there is the occasional trip when her suitcase is inevitably a "hot mess."

"There have been trips where at the end, I know it's all going into the laundry," Swennen said of her sometimes disorganized suitcase.

When packing for a celebrity, she can be so meticulous that she'll literally have folders and garment bags labeling different outfits for each day of the trip. )She noted she enjoys tidiness.) While self-packing a suitcase doesn't necessarily require that level of organization, it is a source of inspiration.

"The key is obviously keeping it as organized as you can throughout the trip," she said.