The Maine Outfits That Got Me Excited to Dress for Fall Again

I just settled back in after several days of a family vacation through various parts of Maine and, if anyone was wondering, traveling with small children is exactly as they say: relocation, not relaxation. Jokes aside, I had a blast, and getting farther north on the East Coast made me excited for early fall weather and the possibility of wearing pants and sweatshirts again.

The rhythm of the weather is a little different up there, so I had to get used to mornings starting quite cool before giving way to strong sun (and vicious mosquitoes). Layering is key when packing for this part of the world. Since this was a family vacation with very full, active days and cozy nights in, the sartorial pressure was off, but I still managed to pull together some fun ’fits worth sharing.

Hippie-feeling graphic tees, cargo pants, sweatshirts, stripes, denim skirts, and florals were in steady rotation. A colorful crossbody, customized mini boat tote, fisherman sandals, playful Prada sandals, suede boat shoes, a classic woven rope belt, and a funky mix of jewelry held it down in the accessories department, lifting everything out of camp-counselor-after-hours territory and giving the looks a little edge.

Day 1: Remixed Stripes & Cargo Pants

For what I predicted would be a car-to-dinner day, I wanted to play with a mix of color, texture, and pattern, so I started strong with a striped tee and cargo combo. I recently started selling a secondhand edit of stripes called Stripes Newport (shameless plug), and unfortunately for everyone, this Tao by Comme des Garçons for Ikram tee never made it to the shop floor. Fortunately for me, it landed straight in my closet and has been in weekly rotation for the second half of summer.

As the philosophy of Stripes Newport goes, everyone loves and looks good in a stripe, and this top is no exception. I love the gentle ruching and sweet pastel crochet sleeves, and it usually gets me a hard-to-come-by compliment from a member of Gen Z.

I loved the idea of a texture-heavy striped tee against my go-to cargo pants from Free People (sadly, almost all sold out), my favorite suede Sperrys from their Aritzia collab (on major sale now), and my faithful Lindquist Object Faba crossbody bag.

Day 2: Colorblocking with Preppy Florals

I recently acquired this old Ralph Lauren Rugby drop-waist floral skirt in the softest cotton, with a great print and roomy pockets. The pieces from this short-lived era of Ralph were impeccable, and I wish I’d kept more of mine from college. I found this one on ThredUp and continue to keep my eyes peeled for more.

I kept the rest of the outfit pretty classic, with a little “ketchup & mustard” colorblocking: a pop of red from a simple vintage crewneck sweatshirt I’ve had forever and my yellow Lindquist Object crossbody. My favorite white socks and boat shoes were the preppy but practical anchor for a relaxing day of exploring that ended with tacos and ice cream.

Dad Vibes but Add a Fashion Sandal

For an unexpectedly rainy day that turned into a rainy dinner, I didn’t push it very far. My friend I was visiting gifted me this adorable sweatshirt from OG nature-tee purveyor Liberty Graphics, which is based in Maine. The strawberry print is a design from the ’70s and still holds up so well today.

I loved it with my go-to Levi’s “Baggy Dad” jorts to keep things comfy and casual, but I had to save the look with my white whale of secondhand fashion: a highly coveted pair of Prada sandals from 2018 that I finally tracked down in my ideal colorway. The pyramid studs and striped wraparound straps almost contradict each other, but that clash gives the whole thing a more interesting layer without much effort.

Day 4: Mixed Plaids Meets Patchwork

As you might be able to gather, I love mixed-up and reworked classics that add a playful twist to otherwise basic pieces. This double tank in two plaids from Chelsea Mak is right up my alley and was a must-pack when it came to throwing things in my weekender.

I paired it with this long denim skirt from Saint Laurent that I’ve had for close to a decade and my pink Sabah fisherman sandals for a laid-back but interesting last bit of summer. I can see myself wearing this one again in early fall, maybe with a long-sleeve tee layered under the tank and a pair of camp socks with the sandals.

The long skirt also served me well for keeping my legs covered during a sunset outdoor concert where the mosquitoes were also in attendance.

Day 5: Surfer-y Take on a T-Shirt Dress

I wanted to add some ’00s Hollister-esque elements to my retro-feeling Prada T-shirt dress, so I layered a denim mini over it with a classic rope belt, my suede boat shoes again, and a boat tote I’ve been adding flair to all summer long.

I felt like this dress didn’t get as much play as it deserved this summer, so I started thinking about creative ways to style it and landed on the micro denim skirts of my early-2000s high school days, which could practically double as belts. While this one isn’t quite as short, I borrowed the idea to add some unexpected layering to the dress.

The whole thing was breezy enough for supervising a toddler tennis lesson, then doing some local shopping and walking the dog before dinner.

Day 6: Florals for Flowerpicking? Groundbreaking.

I love collecting secondhand pieces from one specific Marc Jacobs collection full of these really gorgeous, bright florals. These red silk shorts are actually my second pair from the collection. I have them in another color, too. They didn’t take up much real estate in my bag since they fold down pretty thinly, but I’m so glad I ended up bringing them along, especially since I had no idea flower-picking at a farm was on the agenda.

I also fell in love with this graphic tee from the super-cool Drift Collective, which has a shop in Portland selling locally designed graphic tees and upcycled pieces that you can customize at their mending station. The Prada sandals might have been a weird choice for the farm, but not for pulling the outfit together.

Day 7: Cargos and ‘90s Nature Tee

As you can see, I was scraping the bottom of the weekender by the time the last outfit came around, but I actually loved where I landed. I’ve been wearing this graphic T-shirt I got my husband for our kid’s bug-themed first birthday almost a little too much this summer. It brings me right back to the “scholastic utopia” aesthetic of my childhood that I miss so much, and it’s such a fun conversation starter.

The colors of the bugs go with everything, and the proportions were perfect with baggy cargo pants. I added my pop-of-red sweatshirt around my shoulders, pink fisherman sandals, and the rope belt for some New England-coded elements.