Best Boots & Dress Shoes50
1. Oak Street Bootmakers Trench Boot
#1 in Best Boots & Dress Shoes of 50 products
"Amazing, 3.5 years in and these puppies are still beautiful. Love these boots, bought them in 2016 and they are still gorgeous and comfortable. (No. 8 Chromexcel)" Read More
2. Timberland 6-Inch Premium Boots
#2 in Best Boots & Dress Shoes of 50 products
"Probably one of the best deals drop ever had. I don't think Ive ever seen timbs go for this price where I live. After 3 years the boots still wear as they're brand..." Read More
3. Massdrop x Carmina Semi-Brogue Oxford
#3 in Best Boots & Dress Shoes of 50 products
"More than satisfied with the pair I've received. I'm usually a US 8.5 - 9 when buying sneakers so that's a UK 7.5/8 but I went with UK 7.5 for this. It is ALMOST a..." Read More
4. Carlos Santos Monkstrap Shoes
#4 in Best Boots & Dress Shoes of 50 products
"Mine just came in and after a round of polishing." Read More
5. J. FitzPatrick Footwear Magnolia Captoe Oxford
#5 in Best Boots & Dress Shoes of 50 products
Inspired by English, Italian, and French footwear design, J. FitzPatrick offers integrative styles that fuse traditional shapes with modern influences and... Read More
6. Caballero Wear Chelsea Boots
#6 in Best Boots & Dress Shoes of 50 products
At Colombia’s Caballero Wear, shoes are handmade with premium leathers by talented artisans who come from shoemaking families. That’s what makes it one of the best... Read More
7. Loake 1880 Aldwych Captoe Oxford
#7 in Best Boots & Dress Shoes of 50 products
"awesome looking shoes, nice presentation when opening box. Worn twice and starting to break-in nicely. Have received compliments on them. Dark brown goes nicely with..." Read More
8. Loake 1880 Buckingham Brogue Shoes
#8 in Best Boots & Dress Shoes of 50 products
"Normally Im between a 9-9.5UK , but doing some research online, I found that the shoe tends to be .5-1 size bigger depending on the foot. I ended up buying 9UK and I..." Read More
9. Thorogood 1892 Beloit Plain-Toe Boot
#9 in Best Boots & Dress Shoes of 50 products
"bougt the brown. Similar to the picture except the leather laces are duller in Colour and the tongue of the boot is very limp ( slides off to the side and bottom of..." Read More
10. Loake 1880 Pimlico Chukka Boots
#10 in Best Boots & Dress Shoes of 50 products
Among the oldest shoemakers in England, Loake 1880 is still run today—five generations after its founding—by the Loake family. Like its founders did in the 19th... Read More
11. Loake 1880 Kempton Chukka Boots
#11 in Best Boots & Dress Shoes of 50 products
"Excellent product. Fit is as described." Read More
12. Carlos Santos Chelsea Boots
#12 in Best Boots & Dress Shoes of 50 products
"Excellent boots. They are durable and made of very nice leather. I get compliments almost every time I wear them. The sizing is normal. I wear a 12 in Nike and wear a..." Read More
13. Oak Street Bootmakers Camp Moc
#13 in Best Boots & Dress Shoes of 50 products
"Great build quality. Once the shoes broke in, they were extremely comfortable to wear. I am already planning on my next purchase." Read More
14. Thorogood 1892 Natural Chromexcel Boots
#14 in Best Boots & Dress Shoes of 50 products
"These boots are excellent! After a night of inebriated debauchery, I stress-tested both the structural integrity and the finish with some spirited downhill running on..." Read More
15. Muroexe Army Unite Sneakers
#15 in Best Boots & Dress Shoes of 50 products
"I've had these now for several months, so I feel I can report on them at last. I only use these shoes for light use; walking only. I don't run in them. Pros: They..." Read More
16. Lanona Porter Boot
#16 in Best Boots & Dress Shoes of 50 products
Made in the United States, Lanona’s Porter boots—measuring 6.5 inches tall—are built for both utility and style. And while they’re normally offered only in black with... Read More
17. Carlos Santos Captoe Oxford Shoes
#17 in Best Boots & Dress Shoes of 50 products
Born in 1942 in São João de Madeira, Portugal, Carlos Santos has grown to become one of the most respected European shoemakers out there. It’s named for its founder,... Read More
18. Carlos Santos Captoe Derby Shoes
#18 in Best Boots & Dress Shoes of 50 products
"I received the black version of these shoes. Value for money is absolutely outstanding. I’m no stranger to men’s dress shoes and own Alden’s, Allen Edmonds, Carmina..." Read More
19. Unbranded Shearling-Lined Boots
#19 in Best Boots & Dress Shoes of 50 products
Lined with 100% sheepskin fleece—including the footbed—these Italian-made boots are the ideal wintertime companion. They feature buttero calfskin uppers and a... Read More
20. Rider Boot "Anders" Hiker Boot
#20 in Best Boots & Dress Shoes of 50 products
"Excellent pair of boots. It was my first pair of boots, and I ordered half a size small due to inexperience. However, it was comfortable, durable and stylish enough to..." Read More
21. HELM Boots Phillips 2.0 Chukka Boot
#21 in Best Boots & Dress Shoes of 50 products
"2 years later and they are still going strong. One of the best pairs of chukkas i own. The leather is tough but once it molds to your feet is comfortable. The leather..." Read More
22. Gorilla USA Hi Boots
#22 in Best Boots & Dress Shoes of 50 products
"Totally Not Needed, Totally Worth It. So I'm an art director spending 80% of my work day staring at a screen, and the other 20% at home, probably also staring at a..." Read More
23. PARC City Boot Co. Event Shoes
#23 in Best Boots & Dress Shoes of 50 products
Event season is here. Weddings, bachelor parties, graduations, summer bashes: wherever you find yourself this summer, you’ll want to look the part. Read More
24. Oak Street Bootmakers Wingtip – Massdrop Exclusive
#24 in Best Boots & Dress Shoes of 50 products
Oak Street Bootmakers was founded by George Vlagos, who fell in love with shoemaking while apprenticing at his father’s shoe repair shop. These days, George strives to... Read More
25. Massdrop x Carmina Oxford Wingtips
#25 in Best Boots & Dress Shoes of 50 products
Made in collaboration with Carmina, a fourth-generation shoemaker in Mallorca, Spain, these oxford wingtips are an exceptional value in the world of dress shoes. They... Read More
26. Thorogood 1892 Janesville Boots
#26 in Best Boots & Dress Shoes of 50 products
Inspired by the first settlers in the American Midwest, the Thorogood 1892 Janesville boots are built for a life of adventure. They feature hand-rubbed Chromexcel... Read More
27. PARC City Boot Co. Chelsey Boots
#27 in Best Boots & Dress Shoes of 50 products
Whether you’re strolling into the office or around town, PARC City Boot Co. has you covered. Read More
28. J. Fitzpatrick Tony II Oxfords
#28 in Best Boots & Dress Shoes of 50 products
The J. Fitzpatrick Tony II has all the elegance of your typical whole-cut oxford, plus an extra bit of flair in the added broguing. Read More
29. Parc City Boot Co. Roundhouse Boot
#29 in Best Boots & Dress Shoes of 50 products
"This is one heck of a boot. I get more comments (good) on these then any of my Allen Edmonds. And they are beyond comfortable. I just wished they were available in..." Read More
30. Thorogood 1892 Kenosha Boots
#30 in Best Boots & Dress Shoes of 50 products
Inspired by Kenosha, a port city in Weinbrenner Shoe Company’s native Wisconsin, these boots are rugged yet refined—and made entirely in the USA. They’re Goodyear... Read More
31. J.Fitzpatrick Madison Loafers
#31 in Best Boots & Dress Shoes of 50 products
The iconic penny loafer gets an update in the J.Fitzpatrick Madison, available in seven color options: three in calfskin and four in suede. Built on the classic round... Read More
32. PARC City Gros Morne Boot
#32 in Best Boots & Dress Shoes of 50 products
"Exceeded my expectations. Leather is not too stiff and not cheaply thin. Breaks in pretty quick. Runs just slightly large (but not more than 1/2 size)." Read More
33. Gorilla USA Chukka Boots
#33 in Best Boots & Dress Shoes of 50 products
Founded in 1906 by Massachusetts ironworkers looking for better shoes to wear on the job, Gorilla USA now makes a range of footwear—from rugged boots to more casual... Read More
34. Danner Caprine Low-Top Sneakers
#34 in Best Boots & Dress Shoes of 50 products
"Danner quality. I’ve had these for 6+ months. Look good for work and for casual use. Comfortable for long walks. As expected quality shoes from Danner." Read More
35. Chevalier Captoe Chromexcel Boot
#35 in Best Boots & Dress Shoes of 50 products
Among the most requested drops in the Men's Style Community, Chevalier's captoe boots are back. Made with a Blake Rapid construction, which allows the boots to be... Read More
36. Thorogood 1892 Mondovi Boots
#36 in Best Boots & Dress Shoes of 50 products
"Excellent boot for the price...." Read More
37. Hanwag Tashi Boot
#37 in Best Boots & Dress Shoes of 50 products
Designed for both city sidewalks and mountain trails, the Tashi boot by Munich-based Hanwag features a hydrophobic upper made of black yak leather, which is sourced... Read More
38. J. FitzPatrick Wedgwood Boots
#38 in Best Boots & Dress Shoes of 50 products
The footwear of choice during Britain’s Victorian and Edwardian eras, the balmoral boot is making a comeback—and bringing a touch of that top-hat-and-coattails flair... Read More
39. Buday Captoe Oxfords
#39 in Best Boots & Dress Shoes of 50 products
The term “hand-welting” is quickly fading from the shoemaker’s lexicon. But there’s no replacing the human touch. Read More
40. Rider Boot Co. Dundalk Reverso Leather Boots
#40 in Best Boots & Dress Shoes of 50 products
The Rider Boot Co. Reverso combines the ruggedness of American workwear with a sleek European shape. Read More
41. Thorogood 1892 Dodgeville Unlined Boot
#41 in Best Boots & Dress Shoes of 50 products
Inspired by the tough-as-nails miners in Weinbrenner Shoe Company’s native Wisconsin, the Thorogood 1892 Dodgeville unlined boots are well suited for any occasion that... Read More
42. Rider Boot Co. Dundalk Boots
#42 in Best Boots & Dress Shoes of 50 products
The flagship shoe of Rider Boot Co., the Dundalk combines the ruggedness of American workwear with a sleek European shape. Like all versions of the Dundalk, each of... Read More
43. PARC City Boot Co. Sable Island Winter Boots
#43 in Best Boots & Dress Shoes of 50 products
"They fit well, are comfortable and look great. Time will tell how they hold up. But so far I’m very happy with the purchase." Read More
44. Nico Nerini Wingtip Shoes
#44 in Best Boots & Dress Shoes of 50 products
"Love them. They are a bit on the stiff side, and will require quite a bit of break-in. However, they fit very well and are comfortable. They look great!" Read More
45. HELM Boots Benson Derby Shoe
#45 in Best Boots & Dress Shoes of 50 products
The first shoe release from Austin, Texas–based HELM, the Benson derby boot transitions from dressy to casual occasions like a champ. It features a rich, lustrous... Read More
46. Oak Street Captoe Boot – Massdrop Exclusive
#46 in Best Boots & Dress Shoes of 50 products
Oak Street Bootmakers was founded by George Vlagos, who fell in love with shoemaking while apprenticing at his father’s shoe repair shop. These days, George strives to... Read More
47. Hanwag Kofel Mid Boot
#47 in Best Boots & Dress Shoes of 50 products
Since 1921, Hanwag has crafted top-quality outdoor footwear from its headquarters near Munich, Germany—and the new Kofel Mid shows this heritage in every sturdy,... Read More
48. Loake 1880 Chatsworth Chelsea Boots
#48 in Best Boots & Dress Shoes of 50 products
"Ordered the black leather option. Love the boots they're absolutely fantastic boots. Quality of the leather is great, the sole is this and comfy (as comfy as they can..." Read More
49. Founders Footwear Captoe Oxford
#49 in Best Boots & Dress Shoes of 50 products
Working with a century-old factory in Naples, Italy, Founders Footwear makes luxury footwear with uncompromising quality. These are the captoe oxfords that founders... Read More
50. Rider Boot Co. Reverse Kudu Chelsea Boots
#50 in Best Boots & Dress Shoes of 50 products
Based on Rider Boot Co.’s classic Chelsea silhouette, these boots stand out for their leather: reverse kudu from England’s Charles F. Stead, one of the most respected... Read More
