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

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

Consider a stay at The Whitney, a hotel gem in Boston’s historic Beacon Hill neighborhood. When you’re ready to change out of their plush robes (with matching ones for the kiddos), cozy up for a cappuccino at nearby Tatte Bakery in a sleek merino wool turtleneck or cozy, cropped cashmere sweater. Pair with slouchy but oh-so-stylish plaid trousers and tortoise-rimmed glasses. For chic footwear that can navigate historic cobblestone streets, give the sneakers a reprieve and consider a modern platform clog. This season’s clogs are understated with a touch of model off-duty style, yet still versatile and comfortable. Whatever your style inspiration, fall is a time for fresh starts. Make it your best back-to-youness yet.

  • What to Pack: Skinny black turtleneck you’ll wear with everything

  • What to Pack: Chic clogs (packing tip: wear them on the plane with cozy socks for minimalist packing)

  • Stay: The Whitney Hotel with bespoke luxury and a prime address on Charles Street in Boston’s darling Beacon Hill neighborhood

  • Eat: Take a short stroll down Charles Street to the coveted Tatte Bakery. Savor a cappuccino while you soak in their gorgeous decor.

Fall Fashion Edit: What to Pack

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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.

Stella Mc Cartney Elyse Clogs

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.