The Fall Boot Guide

Every October, I find myself giving into those crisp fall days and slipping into a pair of boots out of my closet. Let’s face it, those warm summer days are far behind us, and a selection of excellent fall footwear is essential, especially in NYC. Since I start wearing boots later in the fall and through the winter months, versatility in style, color, and boot height is key. I usually gravitate towards classic, simple silhouettes in shades of grey, beige, white, black, or brown. I want the style of boot to transcend from year to year and be staples in my wardrobe that I know I can count on. I’ve found that a great pair of high-quality boots always proves to be worth the investment season after season since they tend to stay looking fresh and hold up best long-term. To get myself into the spirit of the cold weather seasons, I always get excited about adding a new boot style into my wardrobe. I’m already excited to pair some of my long-time favorites, like my IRO and Stuart Weitzman boots, but the new season has me longing for a refresh. Today I’m sharing my Fall Boot Guide to hopefully spark some ideas on your next fall purchase and give my top tips for styling different boot silhouettes. Also, I may or may not have already splurged on some of the styles I am sharing today because some of them are just too good to pass up!

Styling boots usually start with what I’m wearing. For jeans and pants, I usually prefer short booties with a medium-size heel. If you know me, you’ll know I like to play on my height, so I am not afraid of a pretty substantial heel on my booties. I love the way a short bootie looks with a relaxed fitting jean, and how the jean hemline sits a little bit below the top of the boot. It gives that effortless feel as you’ve just put together this great ensemble in under five minutes. I even love booties with skinny jeans, especially black jeans, for an entirely different look and an elongated leg.

Simple is best when pairing pants and booties, and I like to stick to similar colors to create a monochromatic look and an overall elegant feel to your outfit. I recently purchased these gorgeous brown Club Monaco boots, and can’t wait to style them this season. They’re such a classic style, extremely comfortable, and also come in white and black leather. Club Monaco and Ralph Lauren are usually the first places I shop when on the hunt for new fall footwear. Last year I purchased these classic and subtle cowboy boots, that have carried over to this season beautifully.

When I want to style a boot with a skirt or dress, I prefer a chunky heeled knee-high boot. I find myself reaching for knee-high or over-the-knee boots most often when I’m wearing these styles. Regardless of the skirt length, tall boots are a perfect extra layer for those chilly days and extends the wear life of your skirt and dresses into the winter season. I prefer a block heel because it lends itself to being much more comfortable and versatile, as opposed to a stiletto. I love this suede style, as this shape pairs beautifully with fall dresses and skirts – both mini and maxi. It just depends on your preference and what look you want to achieve. 

I hope that this helped spark an interest to update your fall footwear and give you an idea of what you need in your boot arsenal. I have curated a selection of styles to choose from, ranging in colors, styles, and prices! Happy boot shopping!