The 8 Things You Should Always Pack for Vacation (and One to Leave at Home)

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If you’re anything like me, the act of packing for a trip consists of putting every relevant outfit you own into a huge bag, zipping it all up and going on your merry way. My traveling ethos is “anything can happen” and when it comes to my packing skills—it shows.

At this point in my life though, it’s not that I don’t know better (I’ve been on enough trips where I in fact, did not need my rainbow sequined heels) it’s just a matter of actually doing better. So, in an effort to change my ways (I am a fashion editor after all), I’ve spent some time thinking about what one actually needs to enjoy a well-deserved trip.

Here, the items that you simply can’t leave without…and one that’ll always take up unnecessary space. Now, let’s hope I can heed my own advice!

Heels are Back, Baby! Here are 20 That You Can Actually Walk In

things to pack for vacation reformation

1. Pack: Something Sleek For A Nice Dinner

No matter what type of trip you’re taking, having a super chic dress (or two) that makes you feel sexy will always leave you prepped—whether that’s for a night on the town with the girls or an intimate candlelit dinner in the yard while your children sleep inside. A slinky LBD or satin option will take up almost no space and get the job done.

Shop similar styles: Reformation ($218), Revolve ($198), Shopbop ($295)

things to pack for vacation hm

2. Pack: Layers For Chilly Nights

This applies to summer beach trips and winter ski trips alike. Layer, layer, layer! I like thin, insulating materials like cashmere and cotton which pack light, but can go on top of each other for max warmth. Whether it’s a knit cardigan or a light denim jacket, you’ll be glad you were ready for that random cold front or frigid plane air.

Shop similar styles: H&M ($70), ASOS ($51), GAP ($36)

things to pack for vacation calvin klein

3. Pack: Extra Underwear For…whatever Comes Up

My mother always told me to pack double the amount of underwear I thought I needed, and I’ve been doing so my whole life without question. We won’t go too far into detail, but there’s really no scenario where this isn’t a helpful tip.

Shop similar styles: Verishop ($35), Everlane ($18), Macy’s ($27)

things to pack for vacation jcrew

4. Pack: A Multi-purpose Hat

A hat is not only an Insta-worthy accessory, it also protects you from passing rain showers, the sweltering sun and even bad hair days that threaten to cast a dark cloud over your trip. Bottom line, you need a hat. Shoot for a wide-brimmed gem or a cute bucket hat that’ll tick every box.

Shop similar styles: J. Crew ($80), Urban Outfitters ($44), Saks Fifth Avenue ($60)

things to pack for vacation anthropologie

5. Pack: Walking Shoes For Fun Excursions

There’s nothing worse than foot pain when you’re just trying to live your best life. Don’t be that friend or family member that has to take a break because you’ve got blisters. Instead, go for simple white sneakers or durable hiking sandals, and be sure to practice wearing them before you leave town…not for the first time as you’re striding onto the airplane.

Shop similar styles: Anthropologie ($40), ASOS ($80), Nordstrom ($50-$80)

things to pack for vacation shopbop

6. Pack: Comfortable But Sexy Footwear

On the other hand, a comfy but sexy shoe is a must to go with that sleek dress you’re got in your suitcase. Shoot for a block heel or platform, both will give you the appeal you’re looking for without compromising the integrity of your arches.

Shop similar styles: Shopbop ($398), Reformation ($198), & Other Stories ($129)

things to pack for vacation and other stories
& Other Stories

7. Pack: An Effortless Dress

What’s better than a dress that you can throw on without thinking twice? Being on vacation and throwing on said dress. I’m talking about a piece that doesn’t need to be ironed, is no-fuss and preferably, has pockets. Opt for a simple cotton number that’ll pack small and won’t need ironing.

Shop similar styles: & Other Stories ($59), Mango ($60), H&M ($40)

things to pack for vacation madewell

8. Pack: A Cute, Compact Bag

In the spirit of packing light, leave your oversized “everything I own is in here” tote home and reach for a simple crossbody bag that won’t weigh you down and will help you feel extra secure while you move about unfamiliar territory. Bonus points if you stuff a fanny pack inside, for the days you want to go totally hands-free.

Shop similar styles: Madewell ($158), & Other Stories ($59), Nordstrom ($118)

Skip: Heels

We know, you thought those stilettos were going to be the main event on at least one night out. And there you were…shuffling about in your Birkenstocks. High heels are barely making the cut in our day-to-day lives, so who wants to deal with them on vacation? Skip this step and pack an extra pair of undies instead. Mom will be so proud.

purewow author

Senior Editor

From 2021-2021 Dominique Hobdy held the role of Senior Editor covering all things fashion, trends, sales and more.