Every fall, fashion and academic calendars intersect, both turning the page from summer’s frivolousness to a fresh new season. As the fashion world gets back to business, academia heads back to the classroom. No matter how long it’s been since you sharpened those No.2 (or more apt, Apple) pencils, fall still captures the back-to-everythingness of it all.

That nostalgia is our style inspiration. A look we’re calling Ivy League Chic—where fashion meets old-school academia, timeless with a fresh twist. Boston, with its leafy streets, historic brick and air of collegiate spirit, is our Where & Wear fall edit style muse and a destination pick for fall travel.

Shop the Look

Where fashion meets old-school academia. Classic with a modern twist and an it-girl ease.

Paravel’s Valise steamer trunk-style handbag is inspired by the era of train travel, a perfect pairing for a classic look with a fresh twist. The unique top-open style means no more digging through your purse for that lip gloss. Added bonus: removable shoulder strap.


Throw on with leggings and a tee for a cozy, minimalist travel outfit or over a satin slip-dress with boots for a weekend brunch. This cashmere and wool blend cardigan is a Vince best-seller and might just be your capsule wardrobe collection’s new best friend.

VINCE $445

Platform clogs have an it-girl ease-of-style and pair with almost everything. Plus they easily maneuver over cobblestone streets and fall leaves. Pair with cozy knit socks or tights for chilly nights. Splurge on this vegan leather version from Stella McCartney you’ll wear all year-round.


Madewell’s Carlton Coat in Houndstooth nails that effortless French girl style. Understated and cozy chic from work to weekend.


Class is in session with Tommy Hilfiger’s Preppy Plaid Pants and matching blazer.


Reading small print never looked so good. Porgy Backstage readers by Caddis Eyewear with lens power from 0.0 to 3.5, in a modern silhouette and classic tortoise look.


A skinny black turtleneck is your wardrobe’s unsung hero for fall/winter style. Our fabric picks are a super-soft modal cotton or a thin merino wool. Keep the fit close to the body for a modern look.

COS $69

Is there anything Madewell’s Relaxed Blazer in Softdrape doesn’t go with? We don’t think so. Sizes petite to plus and under $200. Sign us up.


Travel & Style

Travel Inspiration

Curated Travel Itineraries

Providence, RI

Discover Providence, where old brick meets new art and sunflowers fill an old freeway. Where downtown coffee shops and vegan restaurants meet leafy college campuses and an independent spirit. And the Providence River flows through it all.


Portland, ME

Bring your appetite to Portland, Maine. This charming seaport city is best discovered through its culinary offerings. From fresh-caught lobsters to an innovative food scene worthy of cities much bigger in size, Portland is one of our top USA foodie destinations.



Settle into relaxed luxury at The Whitney Hotel in Boston’s most charming neighborhood, Beacon Hill. Where a local vibe of relaxed style prevails. Meander the charming brick side streets, manicured public gardens and independent shops and cafes. Grab a cappuccino and croissant while you soak it all in.