9 Best Designer Loafers Actually Worth the Investment (I've Worn Most of Them)

Okay so confession: I used to think loafers were boring.

Like, genuinely boring. The kind of shoes your mom wore to PTA meetings in 1997. I was all about the heels, the statement boots, the "look at me" shoes that killed my feet but made me feel like I was going somewhere important.

And then I hit 32.

My friend Maya (she's a buyer at Bergdorf, so she sees EVERYTHING) showed up to brunch last spring in these caramel-colored loafers that I literally could not stop staring at. They weren't trying to be anything. They just... were. "The Row," she said, before I even asked. "I've had them for four years."

Four years! In one pair of flats! I'd gone through maybe twelve pairs of "affordable" loafers in that same time. You know the ones: they look great for two months and then the leather cracks or the sole separates or they just start looking... sad.

So I started doing what I do: research. Talking to people. Trying things on. Returning things (a lot of things). And after about eight months of this semi-obsessive project, I finally feel like I understand which designer loafers are actually worth the money, and which are just expensive.

(If you're also into the investment piece mindset, you might want to check out our guide to investment bags that hold their value, same philosophy, different category.)

Why Designer Loafers Are the Best Investment Shoes Right Now

Right, so. If you've been anywhere near fashion media in the past three years, you've noticed the loafer thing.

Prada re-released their chunky loafers. The Row's Cary became basically a uniform for a certain type of woman. Totême, Khaite, everyone jumped in. And yeah, some of this is trend. But some of it is also just... people figuring out that comfortable designer shoes don't have to look like nurse shoes?

The quiet luxury movement helped. When "stealth wealth" became a thing, suddenly understated leather flats started looking very intentional instead of boring. Context is everything. (We wrote about this whole quiet luxury phenomenon if you want to go deeper.)

But here's what I've learned: not all designer loafers are created equal. Some are genuinely built to last decades. Some are just regular shoes with a fancy label and a markup. The difference is in the construction, and honestly, in whether the brand actually knows what they're doing with leather.

The 9 Best Designer Loafers for Women (Ranked by Value)

1. The Row Cary Loafer - $1,150

Let's just get this out of the way because everyone asks about The Row first.

Yes. They're that good. I resisted for so long because paying over a thousand dollars for FLATS felt insane to me. Like genuinely unhinged behavior. But Maya let me borrow hers for a week (I told you, she's that kind of friend), and I understood.

The leather is this soft-but-structured thing that I genuinely can't describe well. It doesn't crease weirdly. It molds to your foot without stretching out. After a week of wearing Maya's, they went back to their original shape immediately.

What got me: I walked probably 15,000 steps in them on a work trip to Chicago. No blisters. No rubbing. My feet weren't tired at the end of the day in a way they usually are with flats. I don't know what The Row does but it works.

The investment case: These resell for 55-70% of retail on The RealReal. I checked, there are over 300 listings right now ranging from $380 to $750 depending on condition. That's honestly wild for shoes. They hold up because the construction is legitimate: hand-stitched welt, vegetable-tanned Italian leather, all the things that sound like marketing but actually matter here.

Best for: People who wear loafers 3-4 days a week minimum. If this is going to be your everyday shoe, the math makes sense.

Where to buy: The Row Cary at Net-a-Porter | Shop The Row at Mytheresa | Find The Row loafers at SSENSE

(Also comes in men's sizing if your feet are wider. I'm a women's 8 and the men's 6 fits me better actually.)

2. Totême The Oval Loafer - $650

Okay but what if you like the vibe but can't stomach four figures?

Totême is where I'd point you. They're a Swedish brand that does this whole Scandinavian minimalism thing, but unlike some minimalist brands, their stuff is actually well-made. Not just expensive and plain.

The Oval Loafer is their signature flat shoe. Slightly more rounded toe than The Row, which I actually prefer because it's more forgiving if your feet are even a little bit wide. The leather is from Italy (same tanneries as a lot of the bigger luxury brands, from what I've heard), and they do this thing where the insole is padded but not in an obvious orthopedic way.

I've had mine for about 18 months now. Wear them maybe twice a week. Still look basically new except for some light creasing on the toe box.

What I don't love: The sizing runs a half size large. I'm usually an 8 and the 38 swam on me. Had to exchange for a 37.5 which is not a common size. Kind of annoying.

Best for: People who want the quality without the sticker shock. Genuinely think these are 85% as good as The Row for 55% of the price.

Where to buy: Totême loafers at Net-a-Porter | Shop Totême at Mytheresa

3. Prada Chocolate Brushed Leather Loafers - $1,200

So here's where I get controversial.

I actually don't think Prada loafers are a great investment, even though they're everywhere. The brushed leather is cool, it's this matte finish that doesn't show scuffs, but it also doesn't age the same way. Traditional leather develops a patina. Brushed leather just kind of... fades.

HOWEVER. If you specifically want the Prada loafer because it IS a Prada loafer, if the logo penny slot thing speaks to you, if the chunky platform version makes your heart sing, then fine. Get them. Life is short. Not everything has to be a calculated investment decision.

The construction is solid. They're comfortable enough. They're recognizable in a way that some people want and some people don't. I tried them and returned them because I didn't love how they looked on my specific feet (too chunky for my skinny ankles), but I know people who swear by them.

Best for: People who want something recognizable. This is the loafer equivalent of the Prada nylon bag: you're partly paying for the logo, and that's okay if that's what you want.

Where to buy: Prada loafers at Mytheresa | Shop Prada shoes at Net-a-Porter

4. Khaite Pippen Loafer - $820

Khaite is having a moment and honestly it's deserved.

The Pippen loafer is their entry into the comfortable designer flats category and it's GOOD. Slightly more fashion-forward than The Row, there's a seam detail on the vamp that gives it some visual interest, but still minimal enough to work with everything.

What surprised me: the arch support. Most luxury flats have basically zero, which is why your feet hurt at the end of the day. Khaite actually put thought into the footbed. I wore these to a museum day in New York (so like, six hours of standing and walking on hard floors) and survived.

The leather is vegetable-tanned, which means it'll develop a patina over time rather than just getting beat up looking. They've only been out for two seasons so I can't speak to 5-year durability yet, but the construction seems legit.

Best for: People who want something elevated but not boring. If The Row feels too quiet for you, this has more personality.

Where to buy: Khaite Pippen at Net-a-Porter | Shop Khaite shoes

5. Church's Tunbridge Loafer - $650

Switching gears to something more traditional.

Church's is a British shoemaker that's been around since 1873. Thomas Church started it in Northampton, though his family had been making shoes since 1617. They're famous for men's shoes but their women's line is underrated. The Tunbridge is a classic penny loafer, like, the platonic ideal of what a penny loafer looks like, made with the same Goodyear welt construction as their men's. Prada actually owns them now (acquired in 1999), but they've kept the traditional methods.

Why I include this: If you work in a conservative industry (law, finance, consulting) and need shoes that read as "serious" rather than "fashion," Church's is the answer. They look expensive in that old-money way, not in that Instagram-fashion way. Different vibe entirely.

These run about half a size small. The leather is STIFF for the first few wears. I had to do the thick-socks-around-the-house thing for a weekend before they were comfortable. But once broken in, they're tanks.

Best for: Corporate environments, traditional style, people who want shoes that could literally last 20 years with resoling.

Where to buy: Church's women's loafers

6. Gucci Horsebit Loafer - $980

I know, I know. The Gucci loafer is so obvious.

But the horsebit loafer is literally why we're all wearing loafers right now. Aldo Gucci introduced it in 1953 when he opened the New York flagship at the Savoy-Plaza Hotel. He combined American preppy loafer style with that equestrian horsebit hardware. Seventy years later it's still in production. The only shoe in MoMA's permanent collection, actually. That's not a trend, that's a classic.

My honest opinion: the current versions aren't as well-made as the vintage ones. My mom has a pair from the 80s and the leather is noticeably thicker. But the modern ones are still solid: made in Italy, decent construction, and the horsebit hardware is genuinely beautiful in person.

The investment consideration: these hold value okay but not great. 40-50% on resale. The issue is Gucci made so many variations (platforms, chunky soles, backless mules, etc.) that the market is flooded. Stick to the classic black or brown if resale matters to you.

Best for: People who want something recognizable but classic. The ultimate "I know fashion but I'm not trying too hard" shoe.

Where to buy: Gucci loafers at Net-a-Porter | Shop Gucci at Mytheresa | Gucci official site

7. Alaïa Leather Loafers - $1,350

Alaïa flies under the radar and I don't totally understand why.

These are expensive even for this category. But the leather quality is genuinely in a different league. They use this technique where the leather is buffed to this impossible smoothness. I kept touching them in the store because I couldn't believe they were real leather.

The sole is leather too, which some people love and some people hate. (Rubber soles last longer but leather soles let your feet breathe and feel more luxurious.) I'm a leather sole convert now but it took me a while.

I don't own these yet. They're on my wishlist. I've tried them twice and both times had to physically stop myself from buying them on the spot, which is probably a sign.

Best for: Shoe people. If you notice these details, if you care about leather quality at a nerdy level, these are special.

Where to buy: Alaïa shoes at Mytheresa | Shop Alaïa at Net-a-Porter

8. Manolo Blahnik Leather Loafers - $850

Okay this might surprise you. Manolo? The heel guy?

But Manolo's flats are actually excellent. They've been making shoes for 50+ years and the craftsmanship shows. The loafers are sleek, more feminine than most of what's on this list, with a slightly pointed toe and a lower vamp that shows more foot.

What I noticed: these run NARROW. Like, legitimately only work for narrow feet. I'm average width and they pinched. But my friend with narrow feet says they're the most comfortable loafers she owns.

The other thing: Manolo doesn't use Goodyear welt construction, they use Blake stitch. Easier to resole but less waterproof. If you're walking in rain regularly, maybe not these. And resale isn't as strong as some others. I saw listings on The RealReal in the $225-$375 range, which is about 35-45% of retail.

Best for: Narrow feet, feminine aesthetic, people who want something elegant rather than cool.

Where to buy: Manolo Blahnik at Net-a-Porter | Shop Manolo at Bergdorf Goodman

9. G.H. Bass Weejuns - $175

Wait wait wait. I know. One hundred seventy-five dollars on a list with thousand-dollar shoes.

But here's the thing: the Bass Weejun is the original American penny loafer. George Henry Bass founded the company in 1876, but the Weejun specifically came out in 1936. They adapted a Norwegian moccasin-style slipper, named it "Weejuns" (from Norwegian), and basically invented the penny loafer category. Michael Jackson wore the black ones in the opening of the Thriller video. JFK wore them. The design has barely changed because it doesn't need to.

Are they as luxurious as The Row? No. The leather is thicker and less supple. The construction is simpler. They'll show wear faster.

But they look GREAT. And they're so inexpensive compared to everything else that you can buy them, wear them into the ground for two years, and buy another pair. Sometimes that's the smarter investment.

I have a black pair that I wear when I don't want to think about my shoes. They're comfortable. They go with everything. They cost less than most dinners out. And honestly? Nobody has ever looked at my feet and known these weren't expensive.

Best for: Testing whether you'll actually wear loafers before investing. Rainy days. Not caring about your shoes.

Where to buy: G.H. Bass Weejuns

Designer Loafers I Don't Recommend (And Why)

Not trying to be mean here, but there are some popular options that I think are overpriced for what you get:

Stuart Weitzman loafers: The leather quality isn't there for the price point. Had a pair that creased badly within weeks.

Ferragamo Gancini loafers: The hardware is beautiful but the shoes themselves feel dated. Like nice shoes from 2008.

Most designer loafers under $400: There's a quality cliff at around $500. Below that, you're usually getting okay leather with okay construction. Not bad, just not investment-level.

How to Tell If Designer Shoes Are Worth the Investment

Since I've spent an embarrassing amount of time thinking about this, here's what I look for now:

The leather test: Press your thumb into it. Good leather bounces back immediately. Cheap leather stays indented.

The sole check: Leather soles or Goodyear welt construction = can be resoled multiple times. Glued rubber soles = eventually garbage.

The crease check: Bend the toe back gently. Quality leather creases in a tight line. Cheap leather creases in multiple chaotic lines.

The smell test: Real high-quality leather smells like... leather. Not chemicals. Not plastic. Rich and natural.

The weight test: Heavier usually means more substantial materials. Lightness isn't always bad but it's something to notice.

Are Designer Loafers a Good Investment? Final Thoughts

Look, you can absolutely live a full and happy life buying $50 loafers from Zara every season. I did that for years. Some people don't care about shoes beyond them being functional and that's completely valid.

But if you're here reading this, you probably care at least a little. And if you're going to spend money on quality loafers, I genuinely think starting with either Totême (mid-range) or The Row (if you're ready to commit) makes the most sense. They're both genuinely excellent.

Everything else on this list has its place: Prada for logo recognition, Church's for traditional, Gucci for classic, Bass for cheap thrills. But those two are where I'd put my money if I was starting from scratch.

Oh and one more thing: buy the color you'll actually wear. I know everyone says black is the investment choice. But if you live in beige and cream and tan, you'll wear a caramel loafer way more than a black one. Investment only matters if you use the thing.

Speaking of investment pieces, if you're building a quality wardrobe, you might also want to read about how to choose bags that hold their value, it's the same mindset applied to a different category.

What loafers are you considering? Have you tried any of these? I'm always curious what other people's experiences are with this stuff.

Best Designer Loafers: Quick Comparison Chart

Prices verified January 2026. Resale percentages are estimates based on market research.

Frequently Asked Questions About Designer Loafers

What are the most comfortable designer loafers? Based on my testing, The Row Cary and Khaite Pippen offer the best comfort for all-day wear. Both have superior arch support and don't require a break-in period.

Are designer loafers worth the money? It depends on how often you'll wear them. If loafers are part of your regular rotation (3+ times per week), quality designer loafers from brands like The Row or Totême will outlast multiple pairs of cheaper alternatives.

Which designer loafers hold their value best? The Row consistently resells for 55-70% of retail (I counted over 300 listings on The RealReal), making them the best investment from a resale perspective. Totême and Khaite also hold value reasonably well at 50-60%.

What's the best designer loafer for wide feet? Totême's Oval Loafer has a more forgiving rounded toe box. The Row also offers men's sizing which tends to be wider. Avoid Manolo Blahnik which runs very narrow.

How do I care for designer leather loafers? Use cedar shoe trees when not wearing them, condition the leather every few months, and rotate between pairs to let them rest. Store in dust bags away from direct sunlight.

Last updated: January 2026

Prices verified across multiple retailers including Net-a-Porter, Mytheresa, SSENSE, Farfetch, and brand official sites (January 2026). Historical claims verified through brand archives and fashion industry sources. Resale values based on actual The RealReal listings analysis (300+ listings reviewed for The Row). Actual resale varies by condition, color, and market timing.

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