Buying shoes online has never been easy, but thanks to our associate fashion editor Sierra Mayhew, now it is. She zips around the stores of New York City trying on all the trending shoes to report on the comfort, fit, and style so you never have to make a return again.
Anyone who knows me knows that I love a good pair of shoes. I am at a point where I have so many that they line the walls of my apartment. While I’m on the hunt for a new storage solution to keep tabs on my addiction, of course, I’m still shoe shopping.
As a New Yorker, there’s nothing more important to me in a new pair of shoes than comfort. I love wearing heels but I also love walking home so you bet I’m picky when it comes to which style I’ll buy. I recently updated my shoe collection with a few new styles to determine what might be the most comfortable to wear this winter. I’m at a point where I know what to look for when buying shoes so it was surprisingly difficult to narrow this down, but behold the 7 styles that made the cut.
There isn’t an item that’s more difficult to shop for than a heeled mule. It’s a challenge to determine their comfort level simply by looking at a photo online. The brand Larroudé is dedicated to making shoes as comfortable as possible so I always trust anything I buy from them.
Were they comfortable? For a pair of heels that come along with nearly 4 inches of height, most definitely. I wouldn’t wear them to run a ton of errands around the city, but dancing all night is totally doable. How was sizing? 100% true to size.
I get compliments every time I wear my long denim skirt.
If you don’t have a blazer like this already, run don’t walk.
I wore this yesterday and was so cozy.
Stretch boots are having a major comeback and I’m here for it. They’re the kind of boots that hug you in tight and make your legs look insanely long. Most styles I’ve seen are ankle length so this knee-high pair is different and cool.
Were they comfortable? I often feel friction when I try a style like this but the suede is buttery-soft so I faced no problems when I wore them out for a day of shopping. How was sizing? I usually have to go up a half size in European shoes but I stuck with my traditional 39 and it was a great fit.
The leather jacket that I won’t shut up about.
I’ll take as many baby tees as I can get.
This skirt is so fun.
Something about this color looks so good against denim.
Not that long ago, I had a pair of brown croc boots that I was obsessed with. I wore them on repeat to the point that they totally broke and were unsalvageable. I pleaded with my cobbler but it was a lost cause. Finding these boots from By Far was the best thing ever. They’re much higher quality than my original pair and I already know that they go with everything.
Were they comfortable? Absolutely, I could wear them all day. How was sizing? We love a true-to-size moment.
This coat looks so luxe with jeans.
Layering a jacket under my coat is one of my favorite things to do.
Can never have too many cardigans.
Who says you can only wear boots in the winter? I still love wearing my heels on frigid days with a good pair of tights or socks. Since my entire body was as covered as possible, wearing a feminine pair of heels like this brought my look together.
Were they comfortable? Yes and this is why I love platforms. How was sizing? Another win for true to size.
I’d buy this in every color if I had room in my closet to do so.
You deserve to have a pop of color in your closet.
I just lost my earmuffs so these are coming home with me.
If you’re really serious about comfort, you already have a pair of lug-sole boots in your closet. They’re the most comfortable shoe any woman could ever own. Sometimes, they feel extremely casual but something about this all-white pair is just so elevated to me. They were designed by Rosie Huntington-Whiteley so that’s probably why.
Were they comfortable? I’d walk a marathon in them. How was sizing? True to size is really coming to play today.
Layers on layers please.
This is truly the piece you can wear year-round.
Everyone always asks me where I got this.
I legit walked for miles the first time wearing these and it felt like walking on a cloud. All of my coworkers have raved about Vagabond and when I finally tried them myself for the first time, I immediately understood. We’re seeing puffy footwear from Prada and Loewe so you bet I’m wearing it now.
Were they comfortable? The most comfortable shoes in this roundup by far. How was sizing? This never happens but it seems that everything is true to size today.
My first leather coat and I still wear it on repeat.
I love the utility look.
People always are asking about my Linda Farrow’s.
Just when I’d thought I’d seen it all, I found a pair of boots that come with a built-in anklet. I’m not over my obsession with heavy chains so I fell in love with these boots immediately. Plus, I love the slouch.
Were they comfortable? They’re the most comfortable heeled boots I own at the moment. How was sizing? This never happens but it seems that everything is true to size today.
Leather weather.
A black scarf purchase has never disappointed.
Wearing knit maxi dresses feels like walking around in a blanket.
Up Next: We’re Fashion Editors—These Are the Most Comfortable Heeled Boots We Own
