This Is How a Professional Stylist Packs for a Wedding Weekend (and Yes, It All Fits in a Carry-On)

My summer has been bookended by my college roommates’ weddings—with lots of travel for special events in between—and I still haven’t quite figured out the best way to pack for everything. From welcome parties to post-wedding brunches, I almost feel like I need to bring my entire closet for a few days away. 

“It’s wedding season—actually, the whole year can feel like wedding season for some—and destination weddings are becoming more and more popular,” says Andy Drakeford of Andy Drakeford Style, a fashion stylist and personal shopper. 

To take the stress out of preparing for your next destination wedding or other faraway festivity, Drakeford gave us her go-to tactics to efficiently and compactly pack up your essentials.

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1. Create a Thorough Packing List

Of course, you don’t want to forget your toothbrush or a snack for a long flight, but we’re talking about the sartorial situation here. Drakeford suggests writing out a list of all the events you’re attending, the venues, and any potential weather concerns.

“Under each event, list what you’re wearing from head to toe, so you don’t forget anything,” she says. “This includes undergarments, accessories, jewelry, a hat, and for the guys, belts, socks, etc.”

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2. Lay (or Hang) It All Out

Before you head to the airport, hang or lay out each look you want to pack. Drakeford prefers to display hers on a rolling rack. 

“For the ladies, start with the wedding look,” she says. “The dress, shoes, handbag or clutch,  jewelry, and the all-important underpinnings. (And Band-Aids for your feet!) For the guys, that’s the suit or tux, shirt, tie, shoes, socks, cufflinks, and pocket square.”

After laying out your look for the main event, move on to the other parties, like welcome drinks or the rehearsal dinner. If possible, try to see if you can include the same shoes, bag, or other more versatile pieces in multiple events.

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3. Keep Calm and Carry-On

It’s tempting to take advantage of some airlines’ free checked bag policy, but it’s best to stow everything you need for the weekend in a carry-on. 

“Having lost checked bags, had one stolen, and other travel disasters, I firmly urge you to pack a carry-on,” Drakeford says. “I know… you don’t want your dress or suit to get wrinkled. Trust me, you can do this. Take advantage of all the nooks and crannies—zipper pockets, outside pockets, and negative space at the corners can all hold more than you can imagine.”

Drakeford adds that you should put clothing and shoes in a rolling carry-on suitcase and your toiletries (travel-size only!) and anything of value in the carry-on tote you’ll put under the seat.

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4. Rest Easy About Wrinkles

Perhaps the most concerning thing about packing fancy clothes in a carry-on? All those pesky wrinkles that await you upon arrival. Drakeford says there are a few tricks of the trade for a significantly smoother journey.

“To avoid wrinkles, lay plastic dry-cleaning bags between layers and use white gift tissue to stuff sleeves,” she says. “You can also order a travel-size steamer online—it’ll be a lifesaver. They’re also super easy to use and do wonders on wrinkles.”

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5. Strategize Rolling, Folding, and Stuffing

As you fill up your suitcase there are particular items you can roll, fold, or stuff. Here’s how Drakeford breaks it all down:

• Roll: “In the bottom of your suitcase, roll up anything you don’t mind getting wrinkled,” she says, recommending PJs, workout wear, swimsuits, and underwear. “For both hard cases and soft-sided luggage, make sure to fill in the ridges created by the pull up handles.” 
• Fold: Next up, you’ll want to pack each party look, leaving the most fragile or valuable pieces for last. “The fewer the folds in a garment, the better,” Drakeford says. “Can you flatten the dress in one to three folds? Can you fold the suit jacket in half and cross the sleeves over each other?”
• Stuff: Any negative space left behind is ideal for shoes. “Stuff the shoes with socks, undies, and anything else that fits to save space,” she says. “I pack them in dust bags or Ziplocs so they don’t get things dirty.”

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Lighten Your Load

Next, address the bulkier items you need to bring. If you’re packing sneakers or boots, Drakeford says to wear them on the plane to free up more room in your carry-on. 

One other tip to pare down your packing list? Leave your blow dryer at home. “Virtually every hotel has one. Can you do without yours?” she says. 

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