New England Fall Outfits



September 8, 2023

We’re going to New England for Fall ya’ll!

I just completed the final planning stages of our week long trip to New England this Fall. Flights are booked, lodging is confirmed, and one activity is reserved. Now I get to plan for the fun stuff – cute New England Fall outfits.

I love Fall fashion, but I really don’t know what to wear for Fall until I walk outside and see how cold it is. I can’t stand to be cold, so I’m planning these New England Fall outfits in hopes that I’ll be warm enough. I’m bringing backup items just in case some of this doesn’t work out. We are going in late September-Early October so I don’t think it will be too cold; it may be just perfect!

You’ll notice I reuse some of the same items. I do this to simplify my packing and keep weight down.

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mood board of cute New England fall outfits showing a long, flower print dress with brown Chelsea boots, large round sunglasses, and a brown leather purse

Love this Knox Rose dress from Target. The sleeves are billowy and the top portion has a well-hidden button for more coverage if wanted. A tie fits it in the waist, and I would say it’s true to size.

The boots are the Chocolate Knockouts from Thursday Boots. I just discovered this company and the quality, shipping, and return/exchange policy already impress me. I had to exchange mine for a bigger size and it was seamless.

The earrings are a great find on Amazon – only $14 and they’re your new classy, go with everything, dress ’em up or down earrings.

Sunglasses are Simply Vera. I love some big sunglasses and these are just that plus a fun octagon shape. They’re one of my go-to pairs.

I haven’t ordered this purse yet because I don’t know if I trust the site. However, I can’t find the same purse anywhere else. If you order it, let me know what the quality is like! Either way, I’m on the hunt for something similar.

mood board of cute New England fall outfits showing a black turtleneck with blue jeans, a black backpack purse, plaid style sunglasses, and white sneakers.

These sneakers! They are comfortable, low profile, and go with everything. Keeping them clean is hard, but that’s to be expected with white.

Turtleneck from Old Navy. I get so many great staples from Old Navy, like this turtleneck in black and gray. I wore the crap out of them when I was in Germany last Winter. It says it’s “cropped”, but I wouldn’t consider it cropped at all. That may be because I got a large too. Undershirts and turtlenecks are a great choice for cold weather. Also, New England Fall outfits should be layered because apparently the weather changes quickly and drastically some days.

My tried and true Madewell jeans. Love these because they have great stretch, but don’t become baggy after a full day. They’re soft and not too thin or too thick. I’m a 28 and I’m 5’8”, 160lbs.

Same earrings as the first outfit. I like to keep accessories minimal for trips and use a lot of basics – like these white shirts.

Jason got me a black Michael Kors backpack purse for Christmas one year and needless to say, I’m really getting his money out of it. I use it almost everyday. They don’t sell mine anymore, but this one is very similar.

The Burberry sunglasses were also a gift from Jason. Love the plaid and they’re very light.

mood board of cute New England fall outfits showing a chartreuse tank, beige cardigan, black backpack purse, black Chelsea boots, and gold dangle earrings.

Sunglasses are not sold anymore, but they are also Simply Vera. Shop a similar style here and here.

They don’t sell my black backpack purse anymore – this one is very similar.

$14 earrings that I wear ALL the time.

These boots! I bought these right before a two month trip to Europe in the dead of Winter. I ended up wearing them almost every day and I took a lot of shoes to choose from. They were perfect. I didn’t have to break them in, they have great arch support, I could wear them all day, and they’re a classic Chelsea boot style. And when I say all day, I mean all day – walking on cobblestone, in snow, in the rain, up hills, you get the idea. I guess the leather really kept my feet from getting cold too. This is the first time my toes wern’t getting numb while in Europe for the winter.

Tank – True to size, Fall color, and a satin like material. Would be cute for Spring too.

I haven’t ordered the cardigan yet, but the reviews are promising!

mood board of cute New England fall outfits showing a long burgundy coat, white undershirt, gold hoop earrings, large round sunglasses, and white sneakers.

I found a red jacket just like this one at Marshall’s last year. Here is another similar one. I love that you can dress these long coats up or down. I’m always saving photos of the gray ones too.

Tried and true Stovepipe Madewell jeans.

Puma sneakers.


Classic hoop earrings are a wardrobe staple in my opinion. They’re simple and go with everything.

Black clutch bag from Lulu’s. I don’t use this purse often, but I get a lot of compliments when I do. It’s big enough to hold the essentials including my iPhone.

mood board showing a beige sweater with black jeans, black Chelsea boots, and plaid sunglasses.

Classic hoop earrings

Burberry sunglasses – Love these because they are light and durable. I’m rough with sunglasses, so durability is a must.

My go-to cold weather boots! The belt comes off too!

They don’t sell the black Michael Kors backpack purse anymore, but this one is very similar.

The black jeans are from Old Navy. I can’t tell you how many basics I get from Old Navy. They’re great for simple tanks, bodysuits, solid color shirts, chinos, and their jeans fit me really well. These are the high-waisted Rockstar skinny jeans and I actually have them in three colors. The stretch makes them so comfortable!

I love this beige melange sweater. The mock neck keeps me warm, it’s soft, and perfectly cropped. It sits right on top the waist of my high waisted jeans. I have it in black too.

Like what you see?

Making these boards is  fun even if I don’t consider myself a very “stylish” person. However, I do like to think my style is manageable and relatable, so I’d like to know what you think of these 5 cute New England Fall outfits.

I’ll start incorporating more posts like this when I can, but in the meantime, check out these other posts:

How I Finally Got Quality Sleep

How to Spend 24 Hours in Charleston


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