In its many forms, for men, women and children, riding boots are a cool weather fashion essential with a lot of function that has transcended the racetracks, equestrian clubs and polo matches. Runing the gamut from the simple, straightforward design of English riding boots to playful Western cowboy styles, they ensure warmth and foot and ankle support and work for a lot of occasions. Just ask veteran fashion designer Ralph Lauren, who cultivated his decades-long following with the boots along with riding jackets and other garments.

Allan Houser Sculpture Garden. Photo: Equitrekking
Darley Newman, host of public television and Amazon Prime streaming series Travels with Darley, points out choosing the right riding gear is not just about making a fashion statement, but also about being properly equipped for family horseback riding outings as well as a variety of other outdoor activities. Other essentials, such as horse blankets, are also great for added comfort and warmth during fall and winter road trip vacations as well as a must-have for an impromptu picnic or outdoor concert.
Here are a few of her picks:
- Ariat Riding Boots: “For riding boots I love Ariat, as you can see in the photo from a recent shoot we did in Santa Fe for season seven of the show. I’ve been wearing them for years for riding on and off camera! This brand also makes a riding boot that can be used for hiking and for casual outings, which are really comfortable and cuts down on packing space. Ariat also manufactures smartly tailored equestrian jackets and pants in a range of sizes that work off the track and field for work and school.”
- Point Six Socks: “Under those boots, I’m often wearing Point Six Socks, which are as light and breathable as you need them to be and quick drying as you can see here after a morning ride at C Lazy U Ranch in Granby, Colorado. They incorporate new technology so that you’re comfortable in a variety of situations. I always take into account sock length if I’m riding, since you’ll need socks that go up to your upper shins or higher to avoid rubbing from the boots.”
- Victorinox Expandable Suitcases: “I pack all this and more for a well-stocked weekend into my Victorinox expandable suitcase, which can fit everything I need and are really light and sturdy but also look great — basically everything you need in a suitcase!”

Photo: Equitrekking
Websites like SmartPak also offer gear that goes the distance, whether you are an experienced rider, new in the saddle or simply love the clean, elegant lines of equestrian style. Some examples:
- The Piper Waterproof Rain Jacket: The jacket is designed with a flattering silhouette that will suit every figure type, and is available in a range of fun colors and printed linings that will brighten up any rainy day at the barn, on the town or at school. It features a higher zip neck for extra protection from the elements and a handy stowable hood that packs away neatly when you don’t need it.
- Piper Girls Original Breeches with Knee Patch: The popular women’s riding pant, scaled for girls and teens, is cut with a fashionable low-rise design that hits below the belly button for a modern look. They are available in a variety of fun color options so a young rider can show off her style in the riding school ring or other outdoor pursuits during the cooler months. They can be mixed and matched with casual or formal tops. Design elements like Euro seat styling and a wide, contoured waistband eliminate gapping while comfortable, four-way stretch fabric moves with you in the saddle.
Read This Next
Coping with Lost Luggage on a Family Trip
Travel Tips
Sep 4, 2026#WhereverFamily
Insta FeedDestinations / Caribbean
Sep 9, 2026The Bahamas is the Place to Be for the Ultimate Multigen Thanksgiving Experience
This Thanksgiving, family travelers should swap dishes and stress for sun and sand. The Bahamas is emerging as a multigen destination of choice thanks to short flights from the United States, making it easy for the whole family to gather and spend quality time together.
Sponsored Content
GET TO KNOW TAP FORBIZ
Unlock flexible, refined business travel with TAP Air Portugal’s program, TAP FORBIZ. Developed for small, medium and large Companies, with options for corporate events, TAP FORBIZ offers exclusive advantages adapted to each type of business.
Hotels
Sep 9, 202613 Resorts to Consider for Your Babymoon
Expecting a bundle of joy and looking for a perfect spot for a babymoon? Consider these options:
North America
Sep 9, 2026This Golfing Destination Doubles as a Great Family Vacation Spot
A golf trip may not seem like the ideal place for a family vacation — unless the whole family loves to golf. While that isn’t always the case, everyone deserves to enjoy what they love when they get to take time away from life. Luckily, there are some amazing destinations offering the best of both worlds — great family getaways along with world-class golfing.
Sponsored Content
Best of Both Worlds
Enjoy the best of both worlds when you fly with TAP Air Portugal thanks to the Portugal Stopover program. With the program, TAP passengers, whether traveling for business, leisure or both, can stop in Portugal for up to 10 days at no additional airfare on the way to their final destination. What does this mean for travelers wishing to explore by both land and sea? It means after flying to Portugal with TAP and experiencing the country in an entirely new way, travelers can then embark on scenic river and ocean cruises from Portugal’s port cities, or fly with TAP to another European destination.
Destinations / North America
Sep 8, 2026Remembering Dolly at Dollywood
Unlike many entertainment stars, Dolly Parton appealed to all age groups. Her sparkling personality and family-friendly entertainment made her a universal favorite and her theme park in Pigeon Forge, Tennessee, like Dolly herself, appeals to all ages.
ShareThis