The Steele Maiden: Classic New England style with Lands' End in Kennebunkport, Maine

I’ve been itching to go to the seaside town of Kennebunkport for ages and so when I started planning our Maine road trip – I knew it had to get it’s fair share of time to explore. The town certainly didn’t disappoint. Full of classic New England charm (don’t worry, I’ve got a big travel guide coming soon!), I went with an equally classic outfit to match.

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A thick cable knit turtleneck in nautical navy is one of the things I had been mentally picturing myself wearing on this trip for about a month. Real talk: I plan almost all of my outfits based on location ahead of trips. For instance an outfit for ‘window-shopping in Kennebunkport’ or an outfit for ‘dinner out in downtown Portland’. Since I do a good bit of research on the locations we’ll be visiting and what the weather will be like, I can usually plan in advance what will be best fit to wear. This not only greatly reduces the chance of overpacking but it also takes away any stress of getting dressed once I’m there. On a vacation, especially shorter trips, Adam and I like to get up early and hit the ground running so I don’t want to be bothered picking out outfits or worse wishing I had packed something I left behind.  It may seem overly planned, but I’ve been packing this way for years now and I’ll never go back to a randomly stuffed suitcase again.

The Steele Maiden: Classic New England style with Lands' End in Kennebunkport, Maine

But back to the sweater of my dreams. This is it. When I thought of ‘classic New England’ style I knew that Lands’ End would be a great source (I grabbed this striped knit turtleneck and quilted jacket too) because they do that perfect mix of understated stylish and dependably practical. I paired it with a pleated leaf print skirt, gold handbag and these navy oxfords that were favorites of mine since last Fall. My hair was the most unplanned part of my outfit – I originally hoped to wear it completely down but after a veryyy windy trip to Nubble Lighthouse that morning I threw it into this double braided bun and actually love how it turned out. Did I mention it’s good to leave room for spontenaity in a trip?

Lands’ End Drifter Cable Turtleneck Sweater in Navy c/o – wearing a size small | Choies Printed Skirt c/o – under $20! | Charming Charlie Wallaby Joey Bag c/o | BC Footwear Oxfords | Urban Outfitters Sunglasses | Fossil Watch c/o

The Steele Maiden: Classic New England style with Lands' End in Kennebunkport, Maine The Steele Maiden: Classic New England style with Lands' End in Kennebunkport, Maine The Steele Maiden: Classic New England style with Lands' End in Kennebunkport, Maine The Steele Maiden: Classic New England style with Lands' End in Kennebunkport, Maine The Steele Maiden: Classic New England style with Lands' End in Kennebunkport, Maine