I always loved wearing a pair of boat shoes, also known as top siders. There are a ton of reasons why this shoe style is perfect for warm and cool weather alike. I think they’re a cute way of wearing a casual shoe that’s not a sneaker. If you’re going for an ivy league/preppy style or don’t want to tie or mess with the tops of your shoes, then this is the shoe for you. They’re easy to slip on and off, which makes them perfect to wear while you’re traveling. I recently wore this pair on my trip to Nantucket and Newburyport and found them to be comfortable while walking around those quaint coastal towns.
What to Wear with Boat Shoes
So what are some outfit ideas you can wear with boat shoes? I love wearing boat shoes with white jeans, boyfriend jeans, corduroy pants, straight leg jeans, and shorts. I think they’re the essential shoe for anyone who loves to wear nautical looks. Boat shoes are also perfect to wear when the dress code is business casual or smart casual. Both of these dress styles are less formal than business attire, yet appropriate to wear to the office where a closed toe shoe is required. I decided to choose boat shoes as my choice of footwear while in Nantucket, because I didn’t want my foot exposed in the cool weather while walking around town.
5 Outfits With Boat Shoes
The Classic Nautical Outfit
Classic stripes are always a great choice to wear with boat shoes. I wore this stripe tee with white skinny jeans, a navy rain coat, and my boat shoes to walk around town on my first day in Nantucket. The weather was cool, so these closed toe shoes were perfect to wear. In warmer weather, you can switch out the skinny jeans for a pair of white shorts and a short sleeve stripe tee to create a similar classic nautical look.
Outfit Details:
J.Crew Perfect Rain Jacket / J.Crew Striped Tee / J.Crew White Denim Jeans / Sperry Boat Shoes / Celine Sunglasses
Boat Shoes and Boyfriend Jeans
Another reason to choose boat shoes is being able to take them off quickly while traveling. We flew into Boston from Miami and wearing these top siders made it so easy to go through security at the airport. Since boat shoes are basically made to slip on, they become very effective while traveling. I’m wearing my top siders here with this comfy Nantucket travel outfit. The boyfriend jeans, t-shirt, and Natucket sweatshirt looked great with these neutral top siders.
Outfit Details:
J.Crew Nantucket Sweatshirt / J.Crew White Scalloped Edge T-Shirt / J.Crew Boyfriend Jeans / L.L.Bean Tote / Essie Fiji Nail Polish / Celine Sunglasses / Sperry Boat Shoes
Corduroy Pants and Boat Shoes
Corduroy pants are back this season and I think they look amazing with boat shoes. I wore this nautical striped top and corduroy pants when visiting Newburyport in early September. The rubber sole on the shoes made it easy to walk on the boat deck and since it was pretty cold outside, I was happy to not have my feet exposed. This outfit was the perfect shopping day look! Plus, it makes for a comfortable travel day outfit as well, since I wore it to travel home.
Outfit Details:
J.Crew Structured Boatneck T-Shirt / J.Crew Corduroy Pants / Sperry Boat Shoes / Chanel Lipstick
Nautical Look Outfit
I love being able to mix and match my clothes to create more outfits, so in this nautical look I wore a cashmere v-neck sweater with my corduroy pants and navy raincoat. It’s a great outfit to wear while you’re traveling and shopping. I’m also carrying my must have nautical boat tote by LL. Bean.
Outfit Details:
J.Crew Perfect Rain Jacket / J.Crew Cashmere Sweater / J.Crew Corduroy Pants / Sperry Boat Shoes / Chanel Ami Lipstick / Celine Sunglasses / LL. Bean Boat Tote
Casual Shopping Day Look
In this casual shopping day look, I’m wearing these corduroy pants with my new favorite pink sweater that looks great with boat shoes. It’s also a comfy look to wear to work, church, shopping, and lunch. This look was also perfect to wear while hanging out in this houseboat in Newburyport.
Outfit Details:
J.Crew Cashmere Sweater / J.Crew Corduroy Pants / Sperry Boat Shoes / Chanel Ami Lipstick / Celine Sunglasses / LL. Bean Boat Tote
Boat Shoes For Men
I had to add boat shoes for men in this post, because this shoe style is a go-to for my husband and boys. Whenever they need to wear smart casual looks, you can believe they have a pair of top siders in brown leather on. My husband packed his canvas boat shoes for our trip to Nanucket and found them to be very comfortable while walking around the town. He prefers to wear canvas boat shoes to work as well and has them in a two colors.
Men wear boat shoes with shorts, jeans, and pants. They’re the kind of shoe that fits the bill for so many occassions. My husband and boys enjoy wearing socks with their boat shoes. They wear no show socks when they wear boat shoes with shorts and dressy socks when they wear them with pants.
Outfit Details:
Northface Insulated Jacket (similar here) / Sperry (similar)
Shop More Boat Shoes For Women
Want to see more? Read these posts I shared about Nantucket & Newburyport!
WHERE TO STAY, EAT, AND SHOP IN NANTUCKET
J.CREW DATENIGHT LOOK IN NANTUCKET
BLUE FLORAL MIDI DRESS IN NANTUCKET
DINNER IN NANTUCKET WEARING MY FAVORITE DRESS
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The Lord bless you and keep you. Numbers 6:24
All photos in this post were taken while on my trip to Nantucket and Newburyport with the NIR Team.
A big thank you to them for making posts like these possible.
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