Packing for a trip to New England is always a fun challenge. The region’s fickle climate, with intense winters and sudden seasonal shifts, requires thoughtful planning to ensure you’re prepared for anything.
Especially when you’re packing for four days and limited to bringing only a backpack.
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An early May flight from the Concord airport (about twenty minutes from Charlotte) to New Haven brought with it a 40-degree shift in temperature, almost like flipping back pages of the calendar and depositing us in the early days of spring.
The cooler weather was a relief, but the spring showers? Not so much. Thankfully a decade of travel has brought with it plenty of experience in packing for all climates.
As I usually do after returning from a trip, I like to open up my bags and share a peek inside, some real-life outfit photos from the trip, and some insights into packing for that particular destination. I think each city has its own unique personality, and it’s fun to explore it through the lens of fashion.
So, let’s open up my suitcase – err, backpack – and take a look inside:
NEW HAVEN PACKING LIST
Barring my airplane outfit (friendly reminder: always wear your bulkiest items on the plane!), can you believe that all of this fits in my backpack, plus a few other essentials like toiletries, socks, and underwear?
A backpack that packs like a suitcase, coupled with compression packing cubes, works wonders for maximizing the space in a personal item. Combine that with a hardworking wardrobe of mix-and-match pieces, and you’ll never have to pay another airline’s baggage fee again.
If it’s your first time exploring a travel capsule wardrobe, I think it’s helpful to organize everything by category. Here’s a breakdown of why I selected each garment, shoe, and accessory:
Tops
Initially, I pulled a knit white button-down to add a little versatility (adjusting a button or two is an easy way to take a classic piece from day to night), but I quickly realized it would mean that I would need to bring a second bra along, too. Instead, I grabbed my trusty lightweight cashmere sweater and a chic striped long-sleeve tee, layering a super soft short-sleeve tee underneath.
This turned out to be an excellent decision – it was 90°F when we left Charlotte and I was grateful to be comfortable both at my departure point and my destination.
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Bottoms + Outerwear
I very nearly packed one pair of jeans, but with three full days of eating planned in New Haven, decided it would be wise to pack a second pair. With a high stretch content, Universal Standard’s denim (reviewed here) has been my go-to for travel lately.
Choosing outerwear for spring in New Haven was trickier – chilly nights called for something warmer than a light jacket, but not as heavy as a wool coat. My leather jacket is just the ticket for those days in the 50s and 60s, and it fits nicely under my lightweight raincoat.
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Shoes + Accessories
I did some sleuthing before visiting New Haven to learn a little more about local style – did it trend preppy? Casual? Elaborate?
I came up empty-handed and decided to play it safe with my accessories. My rich, brown-toned glove flats and bag added some warmth to my dark color palette, and a pair of well-worn sneakers wouldn’t be too precious in the rain. And I popped in a fun pair of sunnies, just for good measure.
NEW HAVEN OUTFITS
Thursday
I was so glad to have tucked away my cashmere sweater while waiting to board the Avelo plane outside in the 90°F heat, and also so grateful to have it and my leather jacket handy onboard the freezing aircraft. I thought I’d keep them both on while heading for a late-night slice after we landed in New Haven, but it was warmer than I expected. I’m kind of glad – this all-black travel outfit feels like a classic Alyssa look.
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Friday
Does it get any easier than this? Light blue denim, a black tee, a leather jacket, and white sneakers is such a throwback look that finally feels fresh to me again thanks to the speed of the current trend cycle. This look was effortless for tons of walking (and tons of pizza!).
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Saturday
The sun finally emerged, so I started the day in flats before acknowledging that was the wrong call. My feet were swollen from miles of walking, and I could feel the warmth of blisters forming across the top of my foot. After a few hours, we slipped back to the Airbnb where I could switch back into my sneakers. Oh, what a relief.
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Sunday
Our final day in New Haven was dreary, with rain clouds moving in and making the city cold, wet, and windy. My solution to dressing for the weather was a bit unconventional: layering my leather jacket under my rain jacket. It kept the leather dry and protected while keeping me warm. Though it wasn’t my favorite look of the weekend, it was perfectly functional.
*this item is no longer available and a similar is linked
ZIPPING IT UP: FINAL THOUGHTS ON PACKING FOR NEW HAVEN
New Haven style feels quite youthful, thanks in part, I’m sure, to the student population. The looks ranged from colorful and stylish to 90s/00s inspired (think tiny tops and baggy jeans, particularly for going out at night) to “I overslept and almost missed my final” leggings and ratty tee combos.
The takeaway? You can get away with wearing pretty much whatever you want. New Haven skews overwhelmingly casual; unless you’re headed to dine at an upscale restaurant with a dress code, you can get away with comfy jeans and sneakers while visiting the city (which is great, because it practically begs you to explore on foot!).
Heading to New Haven in the Winter? Check out my Winter Packing Lists for Boston, New York City, or Providence for some cooler inspiration
As for this particular packing list, the only thing I would have done differently is leave my flats at home and stay in my sneakers the whole time. Other than that little switch, this felt like a winner. I was physically comfortable in my clothing the entire time, moving easily and never feeling too hot or cold, and also felt fully at home in my outfit choices. While standing out can be a wonderful thing, I prefer to blend in with my destination so I can navigate it with ease.
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Questions for you
Do you tend to reach for more colorful or subdued clothes when traveling?
Where to next? You may also enjoy:
- The Perfect Weekend Getaway Guide to New Haven, Connecticut
- Slice of Heaven: Exploring 6 Can’t-Miss Pizza Joints in New Haven, Connecticut
- Instagram Stories Highlight: New Haven
- Reviewed in this post: Denim from Universal Standard, Able Maha Leather Jacket, Quince Cashmere Sweater
- Traveling Light: A Winter Packing List for Providence, Rhode Island
- Traveling Light: A Winter Packing List for Boston, Massachusetts (in a backpack!)
- Traveling Light: A Backpack Packing List for Philadelphia, Pennsylvania
- Traveling Light: New York City Winter Packing List
- Traveling Light: Albany, New York Packing List
- Avelo Airlines Review
- All Personal Item Packing Lists
- All Travel Guides by Destination
- Checking In: Hotel Reviews
- Shop My Closet
- Exclusive Promo Codes + Discounts
