Living on the East Coast, especially in a walkable city like Boston, means that your shoes are your best companion. As someone who enjoys her everyday strolls — whether it’s heading to Greystone in South End for a morning coffee or for my weekly grocery run to Trader Joe’s — I’ve learned to love shoes that can keep up with me and still look fabulous!
Fall is definitely my favorite time of year here (spring comes almost second). There’s something magical about the fresh air, the rustling of leaves and, in terms of direction, the chance to break out those cozy layers. Along with layering sweaters and scarves, it’s also time for our favorite fall footwear to say hello! Whether you’re trudging through golden leaves or speeding down cobblestone streets, the right footwear makes all the difference.
Here are five of my favorite shoe styles that are best for fall weather in Boston:
- UGGs – The Cozy Classic
UGG seems to come back on the scene every year and it’s easy to see why. My favorite ones are the Women’s Tasman Slipper. The comfort and warmth they offer, right down to the plush fur lining, makes them the ultimate cozy shoe. They’re perfect for those chilly fall walks when the air is slightly harsh, but you still want to feel like you’re walking on clouds.
- Birkenstock Boston Clogs – A comfortable staple
Birkenstock’s Boston Clogs may technically be second on my list of five, but truthfully, they’re my favorite — practically tied for the top spot! With a name like “Boston,” it almost feels like you have to wear them around the city. These shoes are ideal for long walks thanks to its supportive cork base that provides unmatched comfort, especially if you have flat feet or arch pain. Available in tons of shades, my go to is the Taupe shoe. Why are they always out of stock? Probably because they are so desirable.
- New Balance 9060 – The Sneaker Staple
New Balance has had a major comeback over the past few years and their 9060 model is one I’m excited to have back. Whether you’re hitting the gym, or running or heading to work, these shoes strike the right balance between function and fashion. Lightweight and incredibly comfortable, they pair with everything from workout gear to wide leg trousers, making them a great all-rounder for the season.
- Chelsea Boots/Knee High Boots – A versatile must-have
When it comes to styling, another staple is a pair of Chelsea or knee high boots; a staple that looks adorable when styled well. In my opinion, they look the cutest when working with mini skirts (make sure to wear your fleece stockings to stay warm!). Stick to darker tone colors, like dark chocolate, brown and burgundy. These will go with the majority of your outfits, looking sassy as well as not having to purchase that many pairs of shoes!
- Loafers – A timeless classic
Loafers are the definition of understated beauty and have become a go-to for fall with brands like Prada bringing them back into the limelight. While almost every brand now offers them, my pair has been a staple over the last few years. They add an effortless elegance to any autumn outfit, whether you combine them with cropped trousers or a classic trench coat. Plus, there’s something uniquely fulfilling about wearing them at the same time as Boston’s iconic brown and yellow leaves fall — instant autumnal vibes.
Fall in Boston isn’t just about stunning foliage and comfortable sweaters — it’s also about finding suitable footwear to take you from morning coffee runs to night strolls. The proper shoes can make all the distinction, combining consolation, style and a bit of personality. From the coziness of UGGs to the sleek sophistication of loafers, and the flexibility of boots which could pass from informal to elegant, your fall shoe lineup must be as dynamic as the metropolis itself. So, because the leaves change and the air gets crisper, step into the season with confidence and style — Boston is ready, and your footwear is prepared for the adventure!