I love a boot as much as anyone, but loafers may be the hardest-working shoes in my fall closet. They make jeans look a little more polished, keep trousers from feeling too office-y, and give you another option when ballet flats feel too delicate and sneakers feel too casual.
I bought a brown horsebit pair for fall this year, and they’re exactly the kind of shoe I had in mind when I started thinking about this list: polished enough to finish an outfit, but easy enough to wear with jeans on a normal day. You definitely don’t need six pairs of loafers. The trick is finding the one that works with the clothes you actually wear. These are the styles to consider first.
For fall, I went with the Ann Taylor Weekend Horsebit Leather Loafer in saddle brown.
I wanted something classic, but not so traditional that it felt overly preppy. The horsebit gives it just enough detail, while the shape still feels clean and understated. What really sold me was the color. Saddle brown works with so much of what I already reach for in fall — denim, cream, camel, burgundy, navy — and it feels a little softer than black.
I’d wear these with straight-leg jeans and a sweater, cropped trousers and a button-down, or a midi skirt with a simple knit. They’re the kind of shoe that doesn’t need to be the focus of the outfit, but somehow makes everything else look more finished.
If you want a loafer that really looks like a loafer, this is the one. The G.H. Bass Whitney Weejuns has that traditional penny-loafer shape that feels timeless and slightly preppy without being precious. It’s the kind of shoe that works especially well if your closet leans toward button-downs, sweaters, denim, and simple trousers. I’d go with black if you want maximum versatility, but brown or a deep wine shade feels especially good for fall. This is also the pair I’d choose if you like shoes that get better once they’re a little broken in rather than looking brand-new forever.
If you like the look of a classic horsebit loafer but don’t want to spend a lot, the Quince Italian Leather Horsebit Loafer is a good place to start. It has the same polished hardware detail as more expensive versions, but the overall shape is simple enough to work with a lot of different outfits.
I especially like the softer brown shades for fall. They pair easily with denim, cream, camel, olive, navy, and burgundy, and they feel a little warmer than basic black. This is the pair I’d consider if you’re still figuring out how often you’ll actually reach for loafers and don’t want to make a big investment yet.
If the traditional penny loafer feels a little too buttoned-up for you, the Vagabond Alex Loafer has a bit more edge. The shape is more substantial, which makes it a good match for wider jeans and relaxed trousers. It still feels classic, but not delicate. This is also where the proportion of your pants matters. A chunkier loafer can hold its own under a fuller straight leg or slightly cropped wide-leg jean in a way a very slim loafer sometimes can’t. Pair it with relaxed denim, a simple knit, and a jacket, and you’re done.
If you already know loafers are something you wear constantly, this is where I’d consider spending more. The Everlane Made in Italy Loafer has a clean, understated shape that feels more like a long-term wardrobe shoe than a trend purchase.
I like this one with trousers especially. The structure makes a simple tee, sweater, or button-down look more intentional without pushing the outfit into full workwear. This is the pair I’d buy because I knew I was going to reach for it over and over, not because I needed another variation on the same shoe.
If you already own a black leather loafer, I wouldn’t rush out and buy another pair just because fall is here. That’s where suede gets interesting. The Sam Edelman Loraine Soft Loafer gives the classic silhouette a softer, more relaxed feel, especially in a fall shade like olive or brown.
I’d wear it with cream denim, dark jeans, camel trousers, or a midi skirt. Suede adds texture without making the outfit feel busy, and those deeper fall colors can function almost like neutrals. It’s a nice way to add something different without moving too far away from a shape you already know works.
I’d start with either a brown horsebit loafer or a classic penny loafer. Black will always be useful, but brown feels especially easy in fall. It works with denim and all the warmer neutrals that tend to show up this time of year, and it can make an outfit feel a little softer.
Whichever style you choose, pay attention to what you usually wear on the bottom. A slimmer loafer looks especially good with straight-leg and ankle-length jeans. A more substantial loafer can handle a wider leg or relaxed trouser without disappearing underneath it. You don’t need a whole loafer wardrobe. You just need one pair that makes the clothes you already own easier to wear.