I went to Boston this past weekend with Garrett for the Head of the Charles. I love Boston, and I love the Head of the Charles. It’s one of the best regattas in the United States. It’s great for spectators (unlike every other regatta) and feels like a party all weekend long.
This particular weekend was a nightmare weather-wise but still a lot of fun. Saturday it rained pretty much the entire day, even worsening to a downpour in the afternoon. Luckily we stayed at the Lenox Hotel and had access to their tent right by the Eliot Bridge. Their bottomless hot cider and hot chocolates were necessary to keep warm!
On Sunday, wind replaced the rain. We watched the races for the morning and then went back to check out of the hotel and start exploring some of the city. The wind made for a bitterly cold day, but we relished the bright sunshine! I go to Boston almost every year, and October is my favorite month to visit!
After the race, we went to Beacon Hill for brunch. I went to Tatte for brunch with my childhood friend on Saturday, and the line was long, but Sunday it was even longer. This was a common theme. So many people had told us about restaurants that had long lines, and some didn’t take reservations. I didn’t know what we’d be doing so I didn’t make reservations. We ended up waiting about 45 minutes for a table and walked around Beacon Hill while we waited for them to call us!
I only brought two pairs of shoes with me because I didn’t have too much room. I was planning on wearing my ballet flats with this outfit, but the wind was way too cold, so I wore my Hunter Boots again.
What should I have worn? Bean boots.
50% of Boston was wearing a Barbour coat and Bean Boots. No exaggeration here. One in two people were wearing the Barbour + Bean Boot look.
Beacon Hill is so charming. As much as I love Georgetown, I think Beacon Hill might be even cuter. The townhouses are always decorated to a tee, especially in the fall! 
This street was completely glowing with the yellow trees. After brunch, we did a self-guided walking tour to historical sites. (Side note: but I did the “Freedom Trail” tour in high school and it’s worth spending the time! It covers it all!)
Anyway, we went to the Paul Revere House, the Old State House, Faneuil Hall… and shopping on Newbury Street, ha. 
Boston, I love you.
Barbour Beadnell // Cableknit Sweater // Ruffled Shirt // Jeans // Hunter Boots
Going to Boston for Head of the Charles is on my travel to-do list! I love how classic your outfit looks and I hope you all had a wonderful time!
Lauren,
http://www.atouchofsoutherngrace.com
This outfit is so cute! Even though it’s not the typical brunch outfit it absolutely works for a chilly fall day in Boston! 😍
Perfect look for fall! Isn’t Boston so charming? Wish you guys had better weather on Saturday but looks like Sunday was beautiful!
xo elle // https://splashofpreppy.com
Gorgeous pictures! I live so close by but have actually never been to Boston in the fall. Thank goodness the sun came out so you could take these. I’ll have to do the Freedom Trail when I go.
What GORGEOUS photos of you! I love that area of Boston. It’s such a historical, preppy, colonial getaway. I am wearing Bean boots in Alexandria on my page today, because ’tis the season!
xoxo,
Classic Catherine
Loving this outfit! This is almost exactly what I wore (but with bean boots) while exploring the coast in New Haven, CT this past weekend 🙂 Barbour and boots are a perfect combination for those chilly and windy fall days!
-Taylor (www.livingtaylored.com)
I love your style so much! I’m a southern belle through and through and we LOVE prep! Anyways, what do you wear under your jeans / any pants really when it’s cold out? I always struggle with having enough layers on top, but freezing on bottom since I only have one layer between my legs and the wind.
I don’t wear anything– if it’s that cold, I’ll wear tall boots (extra layer to my knees) and then a long parka (extra layer to/past my knees). I actually find that it’s more important to keep my extremities warm, which means wearing: great mittens/gloves, a hat, and warm socks with the right boots. And then wearing a great coat that keeps your chest (heart) warm!
Such a simple and classic outfit! I’m the nut that said hi to you on Sunday morning in like, hour two of my nine hour volunteer shift (windburn city…literally). HOCR weekend is usually cold/windy/rainy sadly. Both years I rowed in it there was a shortened course! It was lovely meeting you and I hope the weather is better next year for you and Garrett to come back!
Your photos of Boston are making me so homesick! I love Boston in the fall- it’s absolutely picture perfect! Unfortunately, I never have the chance to come home from university in the fall, so it’s something I truly miss.
PLEASE make a post about best coats to have for winter time. I’m new to the north and don’t even know where to start for warm coats!
Great idea!!
I’m reading this post while sitting in my grad school office in downtown Boston. I’m currently wearing red hunter tour boots, dark jeans, and my sage Barbour Beadnell is draped over the back of my chair (detachable hood included). You really did nail the preppy Bostonian outfit! (The Bean Boots stayed home today because the forecast is calling for 1 inch of rain later, otherwise they would be my footwear of choice!)
Ah! Love it 😊
It was so great to see you again and meet Garrett! Sorry for getting you all soggy from my raincoat hug but glad you were eventually able to escape the rain!
Lizzy
Perfect fall outfit!
http://thegirlfromconnecticut.com/
This is the perfect fall outfit! I love it.
Love this look! I just bought those boots!
Perfect fall outfit combination! I even wear that combo in the South!! Also, those pictures with the yellow leaves glowing are amazing 🙂
XO Lauren
http://www.loveandlauren.com
Carly, what color is your Barbour jacket? I can’t tell if it’s navy or black 🙂
Navy!
Such beautiful photos and what a backdrop! I’ve always said Boston is my fave city in the whole world (big Red Sox fan! ) xx Rox-Anne, Celebratingthislife.ca
Boston is in my bucket list. I’d love to visit it next time I’m in the US.
That’s so wonderful that you had such a great time in Boston. Actually, I live in the Boston area so when I saw the title for this post I may have screamed a little.😊 You should definitely do a meet and greet in Boston!
Loved this post! Such a cute outfit too! I love Boston!! I went for the first time with my mom a couple years ago and can’t wait to go again!
xoxo,
Abigail
http://www.belleofthebrier.com/
Absolutely LOVE Boston. Up there with my top 5 places I’ve ever been. (The Freedom Trail is definitely a must, at least once!) But I’ve only ever been in the summer – I can’t imagine how gorgeous it must have been in person in the fall! <3
This outfit is so cute, Carly! Love it!
xoxo,
Katie
chicincarolina.blogspot.com