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There are five dress shoes every man should own, and with the holiday season underway, now is the perfect time to gift the special men in your life with new pairs.
A high-quality pair of oxfords or monk straps, or a gift card to his favorite store so he can choose the style he likes best, makes for a gifts that's both thoughtful and practical.
Big names like Cole Haan and Allen Edmonds and up-and-coming companies like Wolf & Shepherdand Paul Evans make truly amazing men's dress shoes.
To better help you get your shopping done, we rounded up our favorite pairs. From loafers and oxfords to Chelsea boots and monk straps, you'll find styles that look sharp and will last for years.
Having trouble figuring out what to get someone for the holidays? Browse all of Insider Picks' 2017 holiday gift guides here.
Jack Erwin Archie Penny Loafer
Loafers are one of the most versatile dress shoe options, which makes them a great gift. He can dress them up with slacks for the office and other formal settings or down with jeans for more casual events. The Jack Erwin Archie Penny Loafer uses a smooth leather and a pointed toe for a very classic look.
Jack Erwin Archie Penny Loafer, $195
Paul Evan Martin Wholecut
If you're looking for a quality shoe that he can keep for years and years to come, the Paul Evans Martin Wholecut is the shoe you want to buy. It features a sleek one-piece design that he can wear on any professional occasion while catching the attention of others. Several colorways are available, but this classic black pair is extremely versatile.
Paul Evan Martin Wholecut, $399
Paul Evans Poitier Double Monk Strap
Monk strap shoes are a great alternative to loafers, if he's into laceless shoes. The Poitier Double Monk features the classic design in a rich oxblood color that's sure to stand out. While these probably won't be his go-to shoe, they're the perfect third or fourth option for when he wants to switch up styles.
Paul Evans Poitier Double Monk Strap, $399
Wolf & Shepherd Striker Chukka
With "dress to perform" as the brand's motto, the Wolf & Shepherd Striker Chukka does exactly that. From the outside, the rich pebble-textured leather of the Bullet colorway and a sleek sloping toe box make this pair look like a very high-quality dress shoe, while the inside boasts a memory foam-padded tongue, ankle collars, and insoles. Any man will appreciate these because they're just as comfortable as they are stylish.
Wolf & Shepherd Striker Chukka, $335
Wolf & Shepherd Blitz Chelsea Boot
The Wolf & Shepherd Blitz Chelsea boots feature a super-soft premium calfskin leather upper and memory foam insoles, which both make for extreme comfort. The elastic on the sides of the shoes allows for easy entry, and there's no need to break them in. They're taller than most other shoes in this style and have a sharp and sleek toe, which makes them really stand out. He'll be able to wear these both professionally and casually.
Wolf & Shepherd Blitz Chelsea Boot, $425
Jack Erwin Noah Quarter Brogue Oxford
At less than $200, the Jack Erwin Noah Quarter Brogue Oxford is a stylish look that won't empty your pockets. The brogue detailing is featured on the toe box and side panels, creating a timeless look he'll appreciate for years to come.
Jack Erwin Noah Quarter Brogue Oxford, $195
Vince Camuto Tallden Wingtip
The Vince Camuto Tallden features a brown leather upper with the signature cap-toe design wingtips are known for. While many dress shoes go for a premium price, this pair comes in at $129.90. They feature a design he'll love at an affordable price.
Vince Camuto Tallden Wingtip, $129.90 (Originally $195) [You save $65.10]
Allen Edmonds Verona II Italian Loafer
If his shoe selection could use some elegance, then the Allen Edmonds Verona II Italian Loafer is the perfect gift choice. Featuring a smooth Italian calfskin leather upper and a silver midfoot accent, he'll be able to wear these to the most formal of occasions.
Allen Edmonds Verona II Italian Loafer, $375
Cole Haan Cambridge Wingtip
The Cole Haan Cambridge Wingtip is made of premium leather and uses an elegant brogue pattern throughout. If classic wingtips aren't flashy enough for him, then these are the way to go.
Cole Haan Cambridge Wingtip, $159.90 (Originally $260) [You save $100.10]
Cole Haan Pinch Grand Tassel Loafer
If the classic penny loafer is a bit too boring for his liking, the Cole Haan Pince Grand Tassel Loafer is a great alternative. It features a papaya-colored leather and tassel on the forefoot.
Cole Haan Pinch Grand Tassel Loafer, $170
The Rail Hudson Wingtip
The Rail Hudson takes a classic wingtip design and wraps it in a grey suede. A contrasting brown Goodyear welt sole completes the design. If he already owns a lot of leather dress shoes, these will be a great addition to his shoe selection.
The Rail Hudson Wingtip, $99.95
Jack Erwin Ellis Chelsea Boot
A sleek pair of black Chelsea boots can complement any man's style, and the Jack Erwin Ellis is one of the best choices to do so. The shoes are handcrafted in Spain using full-grain leather and feature rubber outsoles — an attribute that makes them good for any season.
Jack Erwin Ellis Chelsea Boot, $220
Cole Haan Harrison Double Monk Strap
Cole Haan's Harrison Double Monk Strap uses a premium smooth leather upper and the brand's innovative Grand.OStechnology, a lightweight system designed for flexibility, traction, and energy return. With an undeniably classic design, these will instantly elevate any guy's professional style.
Cole Haan Harrison Double Monk Strap, $139.90 (Originally $220) [You save $80.10]
Stacy Adams Madison II Cap Toe Lace Boot
Drawing style elements from a traditional cap toe dress shoe, the Stacy Adams Madison II is a boot that can be worn formally. It features a smooth tan suede upper with brogue accents, Goodyear welt construction, and thick rubber outsoles. With these, he'll be able to maintain a professional look even if the weather is bad.
Stacy Adams Madison II Cap Toe Lace Boot, $180
Magnanni Golay Cap Toe Oxford
Made in Spain, the Magnanni Golay Cap Toe Oxford features a two-tone burnished leather upper. The use of leather extends to the inside liner and insoles. If high-quality dress shoes are his weakness, then you can win the holiday season with this pair.
Magnanni Golay Cap Toe Oxford, $435
Amir Ismael Editor, Insider Reviews Amir Ismael is an editor for Insider Reviews, Insider's e-commerce branch of the service journalism team. As a collector of sneakers and fashion, Amir is passionate about all things related to style. He's covered everything including the industry's shift to producing more sustainable clothing, the most comfortable loungewear, all of the best places to shop for affordable business casual attire, and more. He's used his expertise in footwear and the footwear industry to review all kinds of shoes from sportswear giants, well-known casual brands, and startups. Amir's coverage also includes eyewear, watches, and grooming products like electric razors and men's skincare. Since the beginning of the coronavirus pandemic, Amir has led Insider Reviews' face masks coverage with thoughtful recommendations based on CDC guidelines, expert opinions, and his own testing. During his time at Insider, Amir previously handled deals of the day coverage, and worked as a generalist writing hundreds of reviews ranging from phone cases and headphones to bed sheets and blenders, and has also covered major shopping holidays including Amazon Prime Day, Black Friday, and Cyber Monday. Before joining the Insider Reviews team in 2017, worked as a freelance writer for Complex Sneakers and Sole Collector where he contributed to daily sneaker news and release dates, feature-length articles, and interviews with artists, designers, and athletes. Amir graduated from William Paterson University in 2015 with a degree in journalism and public relations. Say hello to Amir at aismael@businessinsider.com or on Instagram @amirjismael. Learn more about how our team of experts tests and reviews products at Insider here. Learn more about how we test style and beauty products. Read more Read lessYou can purchase logo and accolade licensing to this story here.
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