As an Amazon Associate, KIXSZN earns from qualifying purchases. Amazon links are affiliate links. Picks are chosen on merit. Makers that do not sell on Amazon link to their own site, with no commission.
The best monk strap for most men is the Stacy Adams Desmond. It is a cap toe single monk with a burnished leather upper and a cushioned insole in the $75 to $150 tier. If you want two buckles, buy the Florsheim Montinaro. If you want a shoe a cobbler can resole, buy the Goodyear-welted Meermin double monk.
The short version
- Best overall: Stacy Adams Desmond Cap-Toe Monk Strap, a single monk.
- Best dress double monk: Florsheim Montinaro Double Monk Strap.
- Best medallion-toe single monk: Stacy Adams Kinsley.
- Best under $75: La Milano Double Monk Strap.
- Lowest price: Bruno Marc Monk Strap, which has a synthetic leather upper.
- Best Goodyear-welted value: Meermin double monk.
- Best premium double monk: Crockett & Jones Lowndes.
- The original: John Lobb William.
The quick list
The 8 Best Monk Strap Shoes, Compared
| Pick | Straps | Best for | Sole and construction | Price tier |
|---|---|---|---|---|
| Stacy Adams Desmond Cap-Toe Monk Strap | Single | Best overall | Man-made sole, leather upper | $75 to $150 |
| Florsheim Montinaro Double Monk Strap | Double | Dress wear | Man-made sole, leather upper | $75 to $150 |
| Stacy Adams Kinsley | Single | Medallion-toe single monk | Rubber sole, leather upper | Under $75 |
| La Milano Double Monk Strap | Double | Best under $75 | Rubber sole, leather upper | Under $75 |
| Bruno Marc Monk Strap | Double | Lowest price | Rubber sole, synthetic leather upper | Under $75 |
| Meermin double monk | Double | Goodyear-welted value | Goodyear welt | $150 to $300 |
| Crockett & Jones Lowndes | Double | Premium | Goodyear welt | $500+ |
| John Lobb William | Double | The original | Goodyear welt | $500+ |
Tiers reflect typical prices. For how welted and glued shoes differ, see Goodyear welt vs Blake stitch vs cemented.
Best Monk Strap Shoes: The Picks in Detail
Best overall
1. Stacy Adams Desmond Cap-Toe Monk Strap
The Desmond is a single monk: one strap over the instep with a buckle. It has a burnished leather upper, a rounded cap toe with perforated trim, a cushioned insole, and a low stacked heel. It is the best balance here of price, real leather, comfort, and availability.
- Who it is for: a first monk strap for suits, wool trousers, and weddings.
- Fit: the listing gives no sizing note. Check the size chart and recent reviews before you order.
- Drawback: the insole is fixed, so you cannot swap in an orthotic, and the outsole is man-made, not leather.
Best dress double monk
2. Florsheim Montinaro Double Monk Strap
The Montinaro is a cap toe double monk with a leather upper, two adjustable buckles, and a stacked heel. The footbed is lightly padded and the outsole is man-made. It comes in black and saddle tan.
- Who it is for: business suits and formal events, for men who want two buckles.
- Fit: Florsheim says it fits true to size. The listing offers medium width only.
- Drawback: the lining is fabric, not leather, and there is no wide width.
Best medallion-toe single monk
3. Stacy Adams Kinsley
The Kinsley is a single monk with a smooth leather upper and a perforated medallion on the toe. It has a leather lining, a fully cushioned insole, and a rubber outsole. The perforations make it a little less formal than a plain cap toe.
- Who it is for: men who want one buckle, some decoration, and a rubber sole for wet days.
- Fit: the listing gives no sizing note. Check the size chart and recent reviews before you order.
- Drawback: the decorated toe is harder to pair with a formal suit than a plain or cap toe.
Best under $75
4. La Milano Double Monk Strap
A tapered cap toe double monk with a leather upper, a comfort insole, and a stacked heel. La Milano finishes the upper with a painted and brushed effect, so the color is uneven on purpose. It is the cheapest real leather double monk on this list.
- Who it is for: parties, weddings, and occasional office wear on a small budget.
- Fit: La Milano says it runs true to size. The toe is tapered, so check reviews if your forefoot is broad.
- Drawback: the lining is synthetic, and the brushed finish looks less formal than plain calf.
Lowest price
5. Bruno Marc Monk Strap
This is the cheapest shoe on the list. It is a cap toe double monk with a synthetic leather upper, not real leather. It has a soft latex footbed, a rubber outsole, and a stacked heel.
- Who it is for: one event, or trying the double monk style before you spend more.
- Fit: the listing gives no sizing note. Check the size chart and recent reviews before you order.
- Drawback: the synthetic leather upper. It will not soften or take polish the way real leather does.
Best Goodyear-welted value
6. Meermin double monk
Meermin is a Spanish brand that sells Goodyear-welted shoes direct at low margins. Its double monk is a cap toe in calfskin. The welt means a cobbler can replace the sole.
- Who it is for: a first good monk strap for suits and wool trousers.
- Fit: UK sizing, so most US buyers order one size down from their US dress size. Snug over the instep.
- Drawback: Meermin has a reputation for a hard break-in. Plan on several short wears first, as described in how to break in dress shoes.
Best premium double monk
7. Crockett & Jones Lowndes
Crockett & Jones has made shoes in Northampton, England, since 1879. The Lowndes is its cap toe double monk, Goodyear-welted, with cleaner finishing and finer calf than the tiers below.
- Who it is for: men who wear tailoring often and will resole the shoe more than once.
- Fit: UK sizing. Get fitted at a stockist if possible.
- Drawback: price.
The original double monk
8. John Lobb William
John Lobb introduced the William in 1945, and it is the pattern most double monks copy. It has a straight cap toe and a double leather sole, which gives it a sturdier look than slimmer double monks.
- Who it is for: collectors and buyers with no budget limit.
- Fit: UK sizing. Buy in person.
- Drawback: it costs several times more than the Meermin for a similar function.
Best Double Monk Strap Shoes
Six of the eight picks are double monks. The Florsheim Montinaro is the best one in the $75 to $150 tier. Under $75, choose the La Milano for a leather upper or the Bruno Marc for the lowest price. The Meermin is the cheapest Goodyear-welted double monk here, and the Crockett & Jones Lowndes and John Lobb William sit above $500.
Best Single Monk Strap Shoes
Two picks are single monks, both from Stacy Adams. The Desmond has a cap toe and suits business wear. The Kinsley has a medallion toe and a rubber outsole, and it costs less.
If you want a Goodyear-welted single monk, look at Carmina. It makes single monks in Mallorca, Spain, at around the $500 line. Single monks are less common than doubles at every price, so expect fewer choices.
Single vs Double Monk Strap
| Single monk | Double monk | |
|---|---|---|
| Buckles | One, on a wide strap | Two, on narrower straps |
| Look | Plain, quiet | More detail, more noticeable |
| Formality | Slightly higher | Slightly lower |
| Fit adjustment | One point over the instep | Two points, a little more control |
| Availability | Limited | Wide |
| Wear it with | Suits, wool trousers | Suits, chinos, dark jeans |
Both sit between an Oxford and a loafer in formality. Both are fine with a business suit and wrong for black tie. The men's monk strap guide covers the history and outfit rules.
How to Wear Monk Straps
- With a suit: dark brown or black calf, both buckles fastened. Trousers should have little or no break so the buckles show. Brown monks are a strong match for navy, as covered in what color shoes to wear with a navy suit.
- With chinos or wool trousers: brown or burgundy calf, or brown suede. This is where monk straps look most at home.
- With jeans: suede or a rubber-soled pair, with dark, slim or straight denim.
- Socks: plain dress socks that match your trousers. The buckles are the detail, so keep the socks quiet.
What to Look For in a Monk Strap
- Buckle. Solid metal in silver, brass, or gunmetal. Match it loosely to your belt buckle and watch. See how to match a belt to shoes.
- Strap. Leather straps with several holes. Some straps hide a short elastic section behind the buckle, which makes the shoe easier to slip on.
- Toe. Cap toe is the standard for double monks. Plain toe is common on singles and looks cleaner.
- Color. Dark brown is the most flexible. Black is best for gray and charcoal suits. Burgundy works with navy and gray.
- Sole. Leather for suits. Rubber if you walk in rain.
Fit and Care
A monk strap should fit like a lace-up: firm at the heel, a thumb's width ahead of your longest toe, and buckled on a middle hole. The strap only fine-tunes the instep, so do not count on it to fix a shoe that is too long. Measure with the steps in how dress shoes should fit.
Unbuckle the straps to take the shoes off. Pulling them off buckled stretches the strap and wears the holes. Use shoe trees, condition the leather every month or two, and wipe the buckles with a dry cloth. The full routine is in how to care for leather shoes.
Frequently Asked Questions
What are the best monk strap shoes?
The Stacy Adams Desmond is the best pick for most men: a leather cap toe single monk in the $75 to $150 tier. The Florsheim Montinaro is the best dress double monk at that price, the Meermin double monk is the best Goodyear-welted value, and the John Lobb William is the original and the most expensive.
What are the best double monk strap shoes?
By budget: Bruno Marc or La Milano under $75, Florsheim Montinaro from $75 to $150, Meermin from $150 to $300, and Crockett & Jones Lowndes or John Lobb William above $500.
What are the best single monk strap shoes?
The Stacy Adams Desmond is a leather cap toe single monk in the $75 to $150 tier. The Stacy Adams Kinsley is a single monk with a medallion toe for under $75. For a Goodyear-welted single monk, look at Carmina, which makes them in Mallorca, Spain.
Is a single or double monk strap better?
Neither is better. A single monk is plainer and slightly more formal. A double monk is more popular today and shows more detail. Choose a double monk if you want the buckles to be noticed and a single if you want a quieter shoe.
Are monk straps formal enough for a suit?
Yes. A dark leather monk strap works with a business suit and sits just below an Oxford in formality. It is not correct for black tie.
How should monk strap shoes fit?
Like a lace-up dress shoe: snug heel, a thumb's width of toe room, and the strap buckled on a middle hole so you can tighten or loosen it. The buckle adjusts the instep only slightly, so the size has to be right.
Do you leave the top buckle undone on double monks?
Some men do, as a casual style touch. It is optional. For business or formal wear, fasten both buckles.
