What to Wear Where: Road Trip!

JULY 20, 2020

Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip
Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road TripRidgely and Hilary at Hotel Lion d’Or, Amboise, Burgundy

GUEST DIARY• BY: KAREN KLOPP AND HILARY DICK

With Europe still closed to Americans and with the covid pandemic still raging, this might just be the perfect time to pack up your kids and pets and hit the open road. Road Trip! But to make the most of it — especially in the age of Covid — you will need both a bit of planning and a healthy dose of spontaneity.


Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip
Road trip — An evocative phrase that conjures feelings of freedom and adventure.

With that in mind, Hilary and I have put together everything you will need to get yourselves freewheeling and not look back.


Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip
Spoiler alert!

We may be stating the obvious, but make sure your license, registration and insurance cards are up to date. And take your car to be serviced — check fluids, tires, etc. and clean your car out for a fresh start!

Have a spare key made to stash under your vehicle in a Keyfinder.



Then stock the car with other essentials: masks & gloves, chargers, a small cooler, reusable water bottle, container with healthy snacks, paper maps (remember those) in case you lose service, age appropriate travel games, audio, blanket and pillows, tissues, paper towels, cleaning towelettes, peppermint oil or caffeine tablets, a first aid kit. And you might want to consider lumbar support, ahem.



Then, there are certain questions to ask yourself in the planning stage. How long and how far do you want to go? How much time do you want to spend in the car?  What do you want to do along the way?   What are the desired activities — golf, ocean, tennis, hiking, fishing, exploring, none of the above?

I consulted Melissa Bradley of Indagare, our planning guru, on some of her favorite routes.  Indagare is a fantastically curated travel service.  They will not recommend a place that has not been vetted by one of their savvy band of world travelers.  Think of it as an “insider’s” guide.


Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip
Melissa Biggs Bradley with friends when the world was open.

“My particular two favorite summer road trips are coastal.  I love the California coast and have done the Big Sur route twice with my kids once from Santa Barbara up to Carmel and another time from San Fran down to Big Sur. There are wonderful hikes and beaches to stop at along the way and great places to stay with free-standing cottages like Ventana and Post Ranch Inn and Carmel Valley Ranch.   For more information, read Hotels You Can Drive To. 


Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip
Post Ranch Inn.

“I also love driving up the New England coast and taking the ferry to Martha’s Vineyard or going to Newport and up to Maine where again there are great places to stay in free-standing cabins at places like the Castle Hill Inn in Newport and Hidden Pond in Maine. One of my team just this week has been doing a trip through Utah, Idaho and Montana, which is another great road trip that I have done.”


Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip
Ocean House, Watch Hill, Rhode Island.
Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip
Castle Hill Inn in Newport.
Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip
The Beach Plum Inn on Martha’s Vineyard.

So, let’s get down to our area of expertise, What to Wear on a Road Trip? Obviously, where you will be stopping along the way will inform your road outfit.  But the first order is stylish comfort. A skirt,  just above the knee allows for good air circulation on your legs, while it prevents sticking to the seat. I find long pants and jeans to be too restrictive for long rides. Pair it with a cotton blend top — my preference is for sleeves because of the sun’s magnification through the windshield.  And while on that subject, a sun hat, sunglasses and sunscreen are absolutely essentials on the road.  I also love this Staud Tote for its structure to keep items neat and its separate small bag for keeping things organized.  The Vintage Chanel magnifying glass is on The Real Real.  Very handy for small print.



Note: When shopping skirts or dresses online, most descriptions will include the length.  Measure from your shoulder and from your waist to the number of inches that suit your style.





And never underestimate the ease of a perfect LDR, Little Road Dress.





And for shoes, something easy to slip on — sneakers are not my thing. Cork cushions your feet.


Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip
Almer 50, SALE $200

Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip
Athena, $425

And for slipper comfort, a Belgian Loafer is a great go-to for travel. They have been around for ages and the classic style holds up.


Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip

Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip

Let’s see what high style Hilary is packing for the highway.

“My family took road trips when my sister and I were little. To see the U.S., our parents combined driving and flying for what they called a ‘learn ya durn ya trip’. Without cell phones or devices we had to find other ways to entertain ourselves. We did a lot of reading and listening to our  ‘walkmen”… not paying much attention to mom pointing out the sights or in Europe when she read to us from the travel guides.

But I have to think some of it sunk in. One of our favorite things to do was to play with our Flip Paddle sign. We would hold it up to cars and trucks going by saying … Hi or You’re Cute or … and wait for the reaction which led to gales of laughter from the back seat.”

When I take a road trip, unlike Karen, I like to wear pants. White jeans can easily be dressed up when you pull off the road. And I always wear a collared shirt so the seat belt doesn’t rub. Sneakers are easy and comfy but a pair of high heels are always in my bag to chic up my look because you never know who you will run into. I also love to pack fun statement jewelry. So while I keep it simple during the day … I can quickly jazz it up at night.


Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip
Tops: J.Crew Flutter-Sleeve Top, $148 / Glamourpuss Beachcomber Shirt, $150 / J.Crew Western Chambray Shirt, SALE $70. Bottom: AG Jeans, $188. Accessories: J.Crew Drop Earrings, $57 / J.Crew Cabana Oversized Sunglasses, SALE $58 / J.Crew Bembien Sofia Bag, $220 / Coroon Folding Nylon Duffer, $165. Shoes: Loeffler Randall Penny Bow Sandal, $395 / Cariuma Canvas Sneaker, $79

Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip
Arriving at the divine Mansion on Turtle Creek.

A few years ago, I drove my daughter down to Dallas to start school.  Off we went with a car packed to the gills and high hopes for a few days of bonding.  As an early riser, the plan was for me to drive first for about 6 hours while Kell slept and then switch spots.  It didn’t really go as planned as my sleeping beauty snoozed most of the way across America. I didn’t really mind for that was the summer of a David McCullough Audible marathon and he was the perfect companion for my solitary drive.

Our first stop was the historic Homestead Resort in Hot Spring, Virginia.


Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip

Next, and high on my bucket list, was the Peabody Hotel in Memphis just in time for the 5 p.m. Duck Parade. It was packed!


Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip

We would have loved to stay a few days to listen to music and get out on the river,  but onward to Arkansas and my first (and only) speeding ticket.


Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip

Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip

Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip

Third night: Mansion on Turtle Creek, Dallas, Texas.


Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip

So, how to pass the time movin’ down the highway? Traveling with children can be a series of “When are we going to get there?”  To avoid tedium, set a schedule each day of what you are doing when. Create blocks of time for computer & phones, non tech game play, movies, conversations, lunch, nap time, etc.  Also designate pit stops for stretching and exercise.  Some days you will want to stop and see points of interest along your route. We found a great selection of games for children of all ages on Amazon.


Karen Klopp, Hilary Dick, New York Social Diary, What to Wear Road Trip
National Geographic Road Trip Atlas, $14 / Travel Bingo Set, $8 / Road Trip Kit, $24 / Our Moments Provoking Conversation Starter, $18 / Kids Travel Journal, $31 / Adult On Board Game For Grown ups, $9 / Cat’s Cradle Book Kit, $9 / Brain Games Mini, $9 / License Plate Game, $6 / License Plate Travel Sticker Book, $9 / Brain Quest, $8

And just to get you in the mood, or entertainment while on in the car, we have compiled a list of our top road movies —

Family Flicks:
The Muppet Movie 
Mr. Bean’s Holiday  Rated G
Green Book Rated PG 13
Chitty Chitty Bang Bang 

Great  Classics:
Two for the Road 
It Happened One Night 
Grapes of Wrath

Cult Classics:
Easy Rider 
Bonnie & Clyde
Road Warrior 
The Cannonball Run 
On the Road (Jack Kerouac)

With Humor:
Little Miss Sunshine 
Bucket List 
National Lampoon Vacation Rated R


Wherever you choose to roam in this summer of great uncertainty and unease, please be kind and be safe. 

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