New Englander’s Guide to Fall Shoes

September 21st, 2018
Location  •   New England

The perfect shoes for fall in New England



Autumn is officially here and while I’m not quite ready to pull out my wool jackets, I am ready to clear out my closet of tattered shoes and invest in some new fall shoes. Nothing pulls together an ensemble like a classic pair of boots, loafers or mules. Below you’ll get to see a sneak peek of shoe styles I’m embracing this season, specific shoes I’ve owned and loved, and new pairs I’m planning to invest in soon. 

Worth The Investment: 


  • The Riding Boots: Finding the perfect pair of riding boots can seem like an art at times, with so many different colors, heights, calf widths, and designs. Overall, it’s important to hunt around and splurge on the ideal pair to wear for years to come; a good pair of riding boots should last you at least five years come rain or shine.
  • The Suede Flats: Brown Suede flats will never go out of style and are a closet staple for any New Englander. Whether you’re pairing them with a dress or a pair of blue jeans, investing in a comfortable pair is the key to enjoying your autumn adventures. I purchased this exact pair years ago in nude, and am excited to finally have the brown suede style in my closet. While these shoes are definitely an investment, trust me when I say you pay for what you get!

Wardrobe Checklist:

  •    The Rain Boot: New England weather can be unpredictable especially during this time of year, so I carry along my favorite pair of rain boots with me no matter where I go. I’ve had this pair, for several years now, and highly recommend them. Style these shoes over skinny jeans or with kneehigh socks and a corduroy skirt
  • The Tassel Mules: I received these shoes in the mail about a month ago, and already know they’ll be my most worn shoe this season. They are the ideal fall transitional shoe and you can see how I styled them in this post, and many more posts to come.
  • The Little Black Bootie: I’ve repurchased these booties five years in a row now. I wore these shoes every day on my college campus because nothing is more classic than the little black bootie. Pair these shoes with black jeans to elongate your legs and give yourself a fashion-forward look. 
  • The Classic Loafers: These are the quintessential New England fall shoe. I had these shoes on my wish list for three years straight and I’m finally pulling the trigger. I’m sure you’ll see me styling them soon.
  • The Bean Boot: Need I say more, these shoes are New England’s ideal transitional wear as we head into the cooler temperatures of fall and eventually winter. Style these shoes with blue jeans and campfire socks to pull together your ensemble. 
  • The Leopard Heel: Leopard is my favorite fall print, and looks so elegant in this block heel design. Whether you’re styling these shoes for work with wide-legged cropped trousers or jeans for a night out, these shoes are versatile and easy to maneuver in! 

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4 thoughts on “New Englander’s Guide to Fall Shoes

  1. Eli Krans

    This is my first visit and your site is awesome.
    Rain boots are a bit plain, but I guess that’ what brings a cozy feel as well as look. The Cassidy mules are an excellent choice.
    Keep shining you two!

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