I Moved to a "Smaller City," and I See Everyone Wear These 7 Simple Items

Fun fact, everyone—I moved to Boston this year. That’s right, I went from New York to Los Angeles to lovely Beantown. For reference, I’m here because my fiancé took a new job opportunity. I’ll be honest, as a fashion person, I was a bit skeptical about moving to a "smaller city.” (Although, I know, Boston is still larger than most.) I spent my entire 20s and early 30s feeling inspired by the style and design of that big-city life. So it was a major change. But I have to say, while Boston isn’t necessarily a "fashion capital” like NYC or L.A., it does have its own stylish sensibilities thanks to its eclectic mix of people and style types.

On that note, the people of Boston really do step out in a range of forward and unique outfits. But what I’ve noticed, in particular, is that those that walk down Newbury Street and the like seem to have gotten the memo on "Beantown staples.” Yes, the people of my new city all seem to own the same mix of simple items. I’m talking those basic must-haves that more or less act as the foundation of a cool outfit. To give you a more in-depth rundown, I rounded up seven of the key staples in question for you below. And naturally, I also shopped out my favorite silhouettes for each if you want to upgrade your offering and get on that Bostonian level.

1. Denim Jackets

Perhaps it’s due to the current transitional temps, but the jean jacket seems to be the topper of choice amongst Boston women. Rightfully so. It’s easy, practical, and can basically be worn with any type of outfit—whether that’s with a tee-and-jeans situation on the weekend or with a turtleneck and midi skirt for a casual office setting.

2. Crewneck Sweaters

The simple knit I spy anytime I prance down the street is almost always a solid-colored crewneck sweater. Often, it's fisherman-inspired or cable-knit. The outfit formula? Said sweater with skinnies and booties.

3. Practical Black Booties

When it comes to the main boot style, standard black booties are where it’s at. Given the walking nature of the city, streamlined silhouettes featuring more practical, chunkier heels are more popular than stiletto iterations.

4. Cropped Skinny Jeans

The jean silhouette du jour among those in Beantown? Ding, ding, ding—it’s all about skinny jeans. While I really do see a range of jeans, it's the timeless skinnies that take the cake. Also, please note the specific cut that seems to be all the rage is a pair that's slightly cropped for a very right-now feeling.

5. Oversize Totes

Given the fact that many people in Boston commute on a regular basis, I spot oversize totes as the bag choice on the train, bus, and on the streets. But I'm not talking flashy styles; it's really the more basic, simple bags (you know, black or brown leather) that are swung over the shoulders of most people I see.

6. Maxi Dresses

If Boston women are opting for a dress (especially as the temperatures start dipping), it's almost always a maxi dress that hits right above the ankle. It's really no surprise it's a front-runner given its one-and-done situation. Let's face it: City women are busy, so a statement maxi you can throw on with booties and head out the door is naturally going to be a winner.

7. Striped Tees

For layering purposes, Bostonians fully lean into the striped tee look. I legit spot some sort of white-, blue-, and red-striped T-shirt on a regular basis under denim jackets, cardigans, and so on. Hey, you can't beat the classic look.

Next, check out the items every NYC girl is wearing right now.

Opening Image: Getty Images

Bobby Schuessler
Market Director

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent over seven years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retialers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises. He has also worked across a variety of other media brands and fashion retailers like Refinery29, PureWow, Men's Health, and Gilt covering commerce, trend reporting, women's and men's fashion, home, and lifestyle.