In This Article
Towards the end of November, I finally succumbed to the fact that it’s no longer sockless loafers season. The only shoes that will truly keep my feet warm are boots. The trouble with boots is finding a pair that really speaks to me the same way as a playful Mary Jane flat or dapper caged sandal does. To feel confident in your boots is to find the one that represents you or adds some umph to your outfit, and isn't just worn out of necessity.
On top of the struggle of styling boots, buying boots always feels like an investment of space in your closet, and, of course, money. It feels like such a commitment because boots should really last you year after year as a cold weather footwear powerhouse, worn day after day. But! After hours and hours and many days of hunting, I think I can finally say I’ve become excited about the boots available for our winterwear. I must preface that these are mainly “fashion” boots, so most are not meant for snow per se (that’s a whole other round up!).
Some tips to start:
- When investing in a boot, go for a classic style. If you’ve seen the same style return from a brand year after year, you know they’re heritage and will stand the test of time.
- When shopping sale. know your brands: Some of my favorite high-quality boot brands are pricey but go on sale! Now is the time to get your deal.
- If you want to go designer but don’t have the budget. Consider pre-owned footwear. Peep places such as The RealReal and Vestiaire Collective. You can find some previously loved styles for good prices. Just make sure you see a photo of the soles.
- For unworn designer shoes, don’t sleep on Gilt, The Outnet, and Yoox.
To make it easy for you to shop, I’ve put together some styles and extra tips, broken down by price point so we can get excited about winter footwear together.
Under $100 doesn’t need to mean boots of low-quality materials that will only fit for a few wears. I’ve found ones I think will stand up to my daily Central Park commute test. Yoox is a wonderful place to shop for quality footwear. A lot of it is discounted or past-season styles, which works well here because ultimately, we’re trying to find boots that don't have a style expiration. I also love Garmentory, which sells cool, smaller brands that not everyone else will have. Mango and Urban Outfitters have both proven to make some of my favorite footwear that have lasted me years (like these creamy pebbled leather-effect boots from Mango and these great tall going-out boots from UO).
Under $200 is really a sweet spot for super classic ankle boots. I love & Other Stories’ options for lace-up and Chelsea boots. I also like to look at Free People, Anthropologie, and Lisa Says Gah for boots that skew a little more fashion in terms of color and stye from both in-house and outside brands. I must mention Clark's Wallabee style, which are such iconic boots that you can wear with jeans or trousers, be comfortable, and look incredibly classically cool. If you're into classic heritage brands, Ariat makes a variety of great western boots in various colors and styles under $200. Etsy is also a great option for small sellers. It’s easiest to shop if you have a specific style in mind, which is how I found a pair of Chelsea boots I love for day-to-day wear.
Under $300 opens up a world of tall boots. Camper and Vagabond are both favorite shoe brands that offer boots under $300 (some even under $200). Both make shoes that are cool, but also very walkable.
Keep an eye out for sales. I love the very useful boots from Diemme, on sale at SSENSE right now. The brand Wal & Pai—an LA-based very high-quality footwear brand—can be expensive, but many styles are currently on sale. Gilt and The Outnet are good places for designer boots at this price point.
At under $400 it gets a bit too easy to shop—the options are endless. When going for something at this investment price, I like to think about styles that are not trendy, but rather super-timeless. Think about ones you have loved for years, or that you can see yourself styling well into the future. A great example for me personally is this style from Free People I'm eyeing (in case anyone I know is reading this and wants to get them for me). I think they are the absolute perfect classic silhouette with a slight western touch that will make them still fun to style.
For some experience with quality brands: I've found that Aeydē and Wandler boots are incredibly well-made, very sleek, and timeless. Spending money on a boot means investing in the next few years, so pick a classic style you really love.