Riding a bike over the hills of Italy (or Switzerland, France or Costa Rica, for that matter) isn’t everyone’s idea of a fun way to take in the local flavor. But for Trek bike guide Jessica Singerman — and the amateur cyclists she shepherds through vacations in the U.S., Europe and South America — it’s one of the best. “Italy and France are two of my favorites. It’s an amazing way to see the country, and the roads are perfect for biking,” she said.
But playing guide means she has to have a versatile footwear wardrobe: bike shoes for the road, comfortable and durable styles for walking, water shoes and hiking boots for the side trips that are part of some tours, and sneakers, sandals and slingbacks for life back home in Philadelphia.
Here, Singerman sounds off on the shoes she loves, what she’s looking for and when the best shoes are sometimes no shoes at all.
Name: Jessica Singerman, 28
Occupation: Travel guide and yoga teacher
Pairs owned: 53
Bike-specific pairs owned: 5
Brands: Adidas, Adrienne Vittadini, Birkenstock, Converse, Dansko, Dr. Martens, Keen, Merrell, Privo and Sidi, among others
Favorite bike shoes: “Sidi Dominator mountain bike shoes. These babies fit great and are bomb-proof. I once had to run the last 6 miles of a 70-mile off-road bike race in them — I had a bike failure — and they were even comfortable then.”
Organizational system: “The bike shoes, hiking boots and running shoes are on a little shoe rack in the living room. The dressy shoes are on a little shelf in the closet. The boots go in one corner of the closet. A random assortment are on a shoe rack in the closet, and all the rest are in a pile overflowing out of the closet. Embarrassing.”
Pair you can’t part with: “I bought a pair of Dr. Martens wingtips in college. I rarely wear them anymore, but I still think they are so cool in a somewhat hideous way.”
Favorite weekend pair: “My Keen flip-flops.”
Most recent purchase: “Montrail water booties for kayaking. They look like ninja shoes.”
Most uncomfortable pair: “A pair of Diesel runners in the wrong size. They were on sale, and I debated between a pair that was just barely too small and another that was just barely too big. I thought these would stretch. I was wrong. I still wear them even though they hurt a little — they’re worth it.”
Next purchase: “I’m looking for the perfect pair of hiking boots for my hike across Costa Rica. Since we will be going through river crossings, they have to drain well and dry quickly. That’s hard to find.”
Dream pair: “I wish they would make my Sidi Dominators in the bronze color again. When these wear out, I will be subjected to buying whatever color they make that season.”
Style you wish would come back: “I’m stumped. Everything has already made a comeback.”
Style you wish would go away: “Uggs, especially with mini skirts. This makes absolutely no sense.”
Favorite dress shoe: “Adrienne Vittadini black slingbacks I got at Goodwill or the Salvation Army — really!”
Best shoe for packing: “My Birkenstock Gizeh thongs. They can look effortlessly dressy, but are still casual. They’re comfy for walking around all day, and stains come right off them.”
Best pair for after a long ride: “None — just bare feet.”