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I just got home Saturday afternoon from a 12-day road trip my husband, daughter, our dog, and I took starting July 6th. We started from the Maryland suburbs of Washington DC and spent two nights in NYC, two nights in Salem, Massachusetts, five nights in a cabin in Vermont, and then two nights in Philadelphia before driving home.
We had a chance to do laundry once in Vermont, and while we brought our car with a rooftop box, we didn't want to overpack, be comfortable in the car, make it easy to carry luggage in and out of hotels, and pack relatively simply. That being said, I AM a fashion blogger so you know I wouldn't be happy wearing cargo shorts and a quick-dry dress over and over for almost two weeks. So below I share a glimpse into what I wore on a 12 day road trip!
What I Wore on a 12 Day Road Trip
While I will share a complete capsule wardrobe of what I took and wore during our road trip, for now a few photos of what I wore while on the road. We went to nice restaurants, walked miles seeing the sights, saw a ballet in the field of a farm in Vermont, picked wild blueberries, went swimming, got caught in a rainstorm, and did it all while maintaining my personal style and staying comfortable.
NYC: Hot Hot Hot
We stayed near Chelsea, walking to see the Empire State Building, Hudson Yards, The High Line, but also just the vibe of the city. It was incredibly hot out and we did a lot of walking (averaged 20K steps/day) and I wanted to be comfortable while still looking “me.”
For the first day, I wore a dress from the Christopher John Rogers for Target collection I featured in this blog post. With it, I wore these sneakers from HOKA which were comfy right out of the box. My bag is this one from Maxwell Scott (use ALISON10 at checkout to get 10% off) and my sunglasses are from ROKA. I'm also wearing this awesome bracelet from Chico's and old earrings from J. Crew (these are a cool alternative). Under the dress, I am wearing these cooling slipshorts in size L/XL (use WARDROBEOXYGEN15 to save 15%).
This outfit was perfect for walking around the Big Apple. The dress has pockets, and the cotton poplin kept the dress from clinging in the heat. The bag was big enough to carry most anything I needed (hand sanitizer, wallet, face mask, Tide to Go pen, hair pick, this for sunscreen touchups, bandana to wipe my face, lip balm, etc.). And by the way, this is the dog stroller we took!
The dress is no longer available but below I've gathered similar styles at a similar low price:
You may recognize this dress from this post in 2018 and this post from last month. This knit dress is a workhorse and a great choice when traveling. While I wore it with sneakers to walk to the garment district to visit Pari Passu and then wear to lunch, I have worn it with metallic sandals to nice restaurants, Birkenstocks for casual errand running, and in the fall have styled it with a denim jacket and leather flats.
I dressed it up with gold hoops from Baublebar and this sale necklace from Banana Republic. For this look I used my Girlfriend Collective belt bag as a crossbody purse.
The second day in NYC was just as hot so after lunch, we came back to the hotel to cool off and I changed into this dress from Ann Taylor. If you follow me on Instagram Stories you know I wasn't sure about keeping this dress but I am glad I did. It was great in the heat and held up beautifully even when being washed with all the things and thrown in an industrial dryer once we got to Vermont. If it's out of stock check again in a few days; it has already restocked at least once!
I kept the same earrings and necklace from earlier, and switched my essentials back to my Maxwell Scott saddle bag. This look was so comfortable, I wore it into the evening when we went to dinner in Chelsea. Do note sweat did make the straps stretch a bit causing my bra to show, but that wasn't until hours of wear and it bounced back once laundered.
Our last day in NYC, I dressed not just for sightseeing, but getting in the car and driving to our next destination. Nothing comfier for a road trip than the Universal Standard Next to Naked Bodysuit which I reviewed here and styled here.
For this day, I didn't even try to get my curls to work in the heat and the hard NYC water, and just put on a baseball cap. I wore a black bandana around my neck for style… but to also be there to mop my brow. I added the gold hoops to make it look purposeful, and the Girlfriend Collective belt bag was worn around the waist. Again the HOKA sneakers and ROKA sunglasses.
Salem, MA: Rainy and Chilly
For the drive home from the road trip, I again wore this bodysuit with a white graphic tee knotted over it.
I was terrible at taking photos while in Salem. The first night we went to dinner and I wore these white jeans with this blue linen shirt, gold metallic sandals (no longer available but these are similar), gold hoops and necklace, this scarf as a belt, and the Maxwell Scott bag.
The next day I wore this black tank with these black joggers, the gold jewelry, the Girlfriend bag as a crossbody, and the HOKA sneakers. It was a bit chilly so I added a shaker knit cardigan I have from cabi (at least a year ago, you can see it in this photo on Instagram). I added a baseball cap because it was occasional drizzles and there was no point in doing my hair. It then began to rain so I added a packable poncho I've had for over a decade (this one is similar).
That evening, I wore the same outfit minus the cardigan which got drenched, and the poncho, since it stopped raining. Instead, I took a lightweight Breton sweater from Chico's (you can see it in this post; I think this is the same sweater in neutral stripes) which I wore over my shoulders until it got chilly, and then wore it half-tucked over the tank.
Vermont: Casual Vacation Mode
Once we reached Vermont, things got far more relaxed.
Wearing the Universal Standard Swim Shorts I reviewed in this post with the Lands' End Tugless Tank I reviewed in this post. Again the ROKA sunglasses and my white leather Birkenstocks. I also wore these shorts with a black tank and the Girlfriend belt bag, and wore these shorts with a white graphic tee and sneakers.
When we went to Farm to Ballet, I wore the same orange Target dress I wore on the first day of NYC. I added a turquoise bandana at the neck for style but also sweat/keep away the flies. And yes, those are Crocs! Sometimes Crocs are the perfect shoe and I packed them thinking of muddy/soft ground, canoeing, going in the river, etc. They were great for visiting a farm and easy to slip off to dance and feel the grass between my toes.
Gotta bring the glamour! When I visited Pari Passu, the founder Shanna gifted me this gorgrous dress caftan. Stay tuned, I plan on showing how to style it beyond the pool. If it wasn't so hot I would have totally worn it over my NTN bodysuit with the gold sandals and jewelry for dinner out. But here I am wearing it with this swim top and this swim bottom and again my white Birks. BTW use WARDROBE20 for 20% off full-priced items at Pari Passu! The hat is from Chico's (no longer available, this is similar), the sunglasses are ROKA.
I was also bad at capturing photos while in Vermont. This was the last night, we went for dinner at a casual restaurant that has an outdoor dining area with picnic tables, tire swings, and hula hoops. This is the blue linen shirt from Chico's I mentioned I wore in Salem, with these shorts from J. Crew. Not seen, I'm wearing this necklace from Chico's. I also wore these shorts with the previously mentioned lightweight Breton sweater.
Philadelphia: Hot and Humid
In Philadelphia, I ended up wearing the same black dress I wore visiting the Garment District in NYC. I think I also wore this in Vermont!
The last night in Philadelphia, I again wore this tank and these white jeans with my gold metallic sandals. I'm wearing the same blue Chico's necklace I wore in Vermont, and this scarf around my waist as a belt. I'm using the Girlfriend bag as a crossbody.
Clearly, not every outfit was captured, but I hope this shows how you can wear and rewear items to maximize looks without packing a lot of clothing!
A while ago you tried on the orange Christopher John Rogers for Target dress on Instagram and asked for votes and I heartlessly and foolishly voted NO. And then you put it into your grid and looked terrific and I started to regret my no vote.
But then I bought the damn dress for myself. I put it on and thought I looked ridiculous but wore it out anyway and my friends roared with approval. It was such a win.
Thank you for your great blog, your great IG feed, and for getting some of us ladies of a certain age out of our comfort zone!
Alison Gary says
Oh yay Kimberly, I am so glad you got it and it works for you! Thank you for sharing this with me, you made my day!
I love FitFlops for city walking. Very comfy and supportive if you get the back strap. I always pack athletic shoes, but sometimes a pair of sandals just makes the outfit!
Alison Gary says
Those look great!
My family did a trip to NYC two years ago this exact same week (feels like a lifetime ago) – and it was incredibly hot and humid. We did a lot of the same stuff you did in southern Manhattan, it was like deja vu seeing your photos! It is so hard staying cool and comfortable visiting the city, never mind trying to be a fashion blogger at the same time! Nicely done. Sorry Salem was so wet – I live in Boston and it’s likely going to be our rainiest July on record. Not great summer weather – but at least no flooding or wildfires). We’re (fingers crossed) traveling to Ireland at the end of August — will definitely be pulling some inspiration from your post!
I’m in Boston, too, and hasn’t this rain been insane? Even when it isn’t raining much, it’s been a very dreary month. Hope Ireland is bright and green!
This is a very helpful post as I have a week long trip coming up and I tend to overpack. Thank you for all the suggestions (plus your previous capsule post – I took pictures with my cell phone of the capsule for instant packing ideas!) It’s nice to be able to shop my closet and also add some versatile new items!
Oh how I love your travel posts! You did an impressive job with your packing. This is something I struggle with; some trips, I do better than others, but I often tend to bring a bit too much. Over the years, I’ve tried hard to start with my shoes so that I bring pairs that are comfortable & suitable for the type of trip we’ll be on. We went to Chicago in June & I brought 2 pairs of Birks & 2 pairs of tennis shoes. Although I love my Birks dearly, they are not the shoes for tons of city walking (at least not for me). The soles rubbed the bottoms of my feet terribly & made it painful to walk. Switching to tennis shoes was the way to go & I just had to treat myself to a new pair I’d been eyeing for months when we went to Nordstrom’s! 🙂 Anyway, you live in such a fantastic part of the country for traveling & I’ll look forward to more of your posts about your trip!
Alison Gary says
Thanks Lee! And yes, I almost brought two pair of Birks but then remembered they’re not good for city walking. I got blisters one day from my sneakers and socks not aligning and my only backup shoe to wear walking around was my flat gold sandals which have no cushioning or support. It made me think I need some good walking sandals that don’t look too athletic/hiker. But it made me grateful for really comfy sneakers!
Glad to see my comment made it here! Good shoes for city walking are so important!
Ann Marie says
I definitely recommend midform tevas. I live in NYC and bought the midform tevas in fawn and they are very comfortable. I run errands in them. The midform gives more arch support and the fawn color blends in with my skin tone more so they are not so obvious. They are great when it is really hot out and I can’t bear to put on leather sneakers. If summer wasn’t so short and if I didn’t need more arch support to walk around NYC, I would buy the regular tevas in all different colors. I love them.
I also bought the Clarks Un Rio sneaker in white (really a light grey). They are perforated and come in wide sizes (I have a wide foot). They were comfortable out of the box and I wear those when walking around NYC too.
Also, if you want a more affordable athletic sneaker that comes in wide, I got the Nike Revolution 5 in wide. It has a nice wide toe box.
Alison Gary says
I love Tevas, but their toe strap is in the wrong place on me and my pinky toe escapes. I keep trying, hoping I’ll find a style that will work but no luck. They are really perfect.
I have a pair of Ecco neutral flats that are great for walking, but they’re looking a bit dingy. Of course, they don’t make anything like that currently! But if you see them on a discount site (I got these from Zulily really inexpensively), I recommend them.
I’m just back from a six day art camp. I knew we’d have heat up into the high 90s with cold nights and early mornings.I packed plenty of tops and both long and cropped pants and good walking shoes. With that heat, I didn’t figure I could re-wear any top without laundry. Didn’t realize we had laundry facilities till after we arrived.
Weather is certainly a factor when packing
Alison Gary says
it really is! And yes to laundry, if we didn’t know we’d be able to do at least one load once we hit Vermont I would have had to pack much more because anything worn in NYC couldn’t be worn a second time, and a lot from Salem also got sweaty and even muddy from all the rain!
Linda B says
Thanks for sharing your travel wardrobe and ensembles. I find packing for travel to be very stressful sometimes! Most of the time, if I am honest. My dear husband does not really get why I don’t want to pack super-light, like he does. And sometimes, a minimal wardrobe is more practical anyway. We are currently away from home for a long time, and I am missing so many of my sundresses! We have a three week trip planned to Japan in March (if the pandemic is not crazy)–I will need to figure out a stylish, minimal wardrobe for that. Sometimes I think it is easier to do that for winter than summer, though the clothes are bulkier!
Alison Gary says
I packed and repacked so many times for this trip. Some items I wish I brought, some items I never used. It’s always a gamble but yeah, my husband is like two pairs of shorts, one pair of pants, two pairs of shoes and done!
Susan Gawrys says
Loved all your looks, especially the white jeans with the belted scarf. Going to try to recreate that!
I’m interested to learn which items you wish you had brought as stated above. Always a learning experience.
Alison Gary says
I’ll put together a capsule wardrobe and will share what I wish I had and what I shouldn’t have brought. Thing is, I didn’t know exactly what the trip would be like so I ended up bringing more activewear than I used. I wish I brought some sort of windbreaker/rain-resistant jacket that can pack down. The poncho was great but for the days that were just a hint drizzly that would have been great. I was thinking I would regret not bringing my hiking boots or a second pair of sneakers but that all worked out. I was super glad I brought my Crocs instead of any other waterproof shoe or sandal. I loved my blue linen shirt so much I wish I brought a second similar shirt (denim, white, even a pattern in linen/voile/chambray). I could have used a second pair of long pants that were lightweight – like Tencel, linen, even some activewear ripstop sort of fabric I could throw on with a tank and sneakers to do things like build a fire, pick berries, help our cousins with chores around the property.
Susan Gawrys says
Thank you for this thoughtful and very detailed response!
I am about to buy the Thigh Society cooling slipshorts that you recommend, as I recently spent a day NYC wearing Jockey Skimmies and found them unbearable due to the humidity. What length do you wear? Curious as we are the same height.
I’ve been enjoying your travels from afar via Instagram! It looks like you had a wonderful time.
Alison Gary says
I have the 7″ they can be adjusted; I never pull them taught long but still they’re virtually invisible and comfortable underneath.