7 Best Loafers That Have Been a Staple in My Wardrobe for Decades

Updated on 27 Sep at 10:10 am

In elementary school, my uniform required black dress shoes. I was allowed to pick the pair so I went with a pair of Dr. Martens loafers. I have been wearing the style for nearly three decades since.

Actually, if you look through my shoe closet, you will notice that 90 percent of them are loafers. (The other 10 percent are Mary Janes.) Though they are a timeless style they’re especially in vogue right now—in fact, I would call them fall’s ‘It’ shoe. As a self-proclaimed expert in this field, I’ve rounded up some of my comfy tried-and-true picks, pairs on my wishlist, and more trending styles.

J.Crew Winona Lug-Sole Penny Loafers

J.Crew

I’ve been eyeing these loafers for a while, and their time may have finally come thanks to a 50 percent discount. These are a classic pair of penny loafers but with a subtle twist—ruching along the upper seams. The sole is thick without being too chunky which makes the shoes “very comfortable,” per one shopper. J.Crew Winona Lug-Sole Penny Loafers are available in three colors: black, silver, and brown (not on sale); women’s sizes range from 5 to 12.

Dr. Martens Unisex Penny Loafer

Amazon

I have had some iteration of this Dr. Marten loafer since elementary school. If you haven’t tried a pair from the iconic brand before, here’s everything you need to know—they can be a little tough to break in (but are super comfortable after that), they are sturdy as all hell, and they will last you years. I have flat feet and yet I can walk miles and miles in these without any aches. The Dr. Martens Unisex Penny Loafer is available in women’s sizes 5 through 13.

Steve Madden Radcliff Loafer

DSW

I love a tassel loafer, and this has been my most-worn shoe in the last month. It’s a classic loafer elevated by gold hardware. I have a heavy gait (and the aforementioned flat feet) so I’m surprised at how comfortable they are despite the thin sole. The leather was a little stiff at first but it took one wear to break in with no other side effects like blisters or toe cramps. The Steve Madden Radcliff Loafer is 25 percent off at DSW with the code GETCOZY and available in women’s sizes 6 through 10.