From Oxfords to Sneakers: The 5 Styles of Shoes Every Guy Needs

Pick one pair of shoes from the following categories and your footwear needs will be covered for the majority of life’s adventures. These are the essential shoes that every stylish guy needs to manage weddings, job interviews, work, travel, dates, and the like. They’re the foundation on which you can build onwards and upwards from. Each pair of shoes on this list meets the following criteria:

• Covers multiple, common situations
• Affordable options are easy to find
• They lean more traditional (nothing too bizarre/super modern)

 

#1. The Mandatory Black Oxford

• J.Crew Ludlow Cap Toe Leather Oxfords – $248 (shown above, review here)
• Allen Edmonds Dainite Rubber Studded Sole Fifth Avenue Cap-toe Oxfords – $265.30 ($425)
• Allen Edmonds Park Ave. – $425 (AE offers 15% off full MSRP for Students, Active Military, and Veterans.)
  
• Grant Stone Cap Toe Oxfords – $340
• Spier & Mackay Blake Stitched Cap Toe Balmorals – $178
• Cole Haan Hawthorne – $97.49 w/ SUNKISSED (weird code, but it works. Expires 8/11)

There’s no getting around it; you need a pair of formal black dress shoes in your closet for those important events in life – professional job interviews, elegant weddings, somber funerals, etc. They might be the least worn pair of shoes in your closet, but when the time comes and you need them, you’ll be glad you have some good ones. A more conservative option is warranted here, so avoid excessively busy details like broguing.

 

#2. The Indispensable Brown Dress Shoes

• Allen Edmonds Fifth Avenue Cap-toe Oxfords – $244.30 ($425) (shown above)
• Spier & Mackay Blake Stitched Balmoral Cap Toe Oxfords – $178
• Grant Stone Longwing Bluchers – $380
• Allen Edmonds Strand – $395
• Charles Tyrwhitt Leather Oxford Brogue Shoes – $207.20 w/ CRISP ($259)
• Brooks Brothers Full Grain Bluchers – $124.99 ($248)
• Nordstrom Elliot Derby Lace Ups – $99.95

Brogues or a style that’s more simple. That’s up to you. For most, brown oxfords or derbys are the most versatile set of footwear in their arsenal. These can be paired well with just about everything from traditional business suiting, all the way down to weekend wear like sport shirts and denim. There are a lot of options when it comes to specific styling and details. Choosing a particular style that fits your aesthetic and dress code can go a long way:

• Generally, the more broguing one of these has the more casual it’ll lean.
• Oxfords (aka balmorals) with their sleeker, closed lacing setup lean more formal. Derbys (aka bluchers) with their open lacing usually aren’t as formal.
• Here’s an Oxford vs Derby side by side to help tell the difference.
• Remember that darker brown leans more formal and lighter shades could be more eye-catching.
• Don’t forget to match your belt, too!

 

#3. The Obligatory Boots

• Grant Stone Diesel Boots – $395 (shown above, review here)
• J. Crew Kenton Chelsea Boots – $209.50 ($298)
• Alden 403 Indy Boots – $680 review here
• J. Crew Goodyear Welted Kenton Pacer Boots – $298 often but not always on sale
• Rhodes Portland Boots – $250
• Rhodes Tyler Chukka Boots – $175 review here
• Thursday Boots Scout Chukkas – $149
• Bespoke Post Line of Trade Lug sole Chelseas – $49 for members – $70

Everyone knows that one friend who wears shorts in the dead of winter and refuses to put on pants. That’s many of us, only with boots. There are just so many styles. A lot of us wear boots 90% of the time because they’re the perfect choice for a super versatile style. For office workers who prefer a smart casual vibe, trade in your Oxfords and bluchers for some boots and pair those with a sport shirt (Oxford, Flannel, Polo, etc.) and flat front khaki chinos or denim. If you’re a frequent traveler, invest in some slip-on Chelsea boots, chukkas, or Jodhpurs.

 

#4. The Essential Casual Shoes
(of which there are many varieties)

• Made in the USA Rancourt Read Boat Shoes – $288
• J. Crew MacAlister Desert Boots – $109.50 ($158)
• Made in Italy Astorflex Fastflex Suede Loafers – $168 ($225)
• Brooks Brothers Hampton Suede Slip-Ons – $149.99 ($298)
• G.H. Bass Hampton Boat Shoes – $69.97 ($128)
• Clarks Bushacre 3 – $89.99 (review here)
• J. Crew Camp Mocs – $129.50 ($188)
• Rothy’s The Driving Loafer – $189

For those casual Fridays and other days where you’re taking it easy but still want to look put together, opt for a more relaxed and comfortable pair of penny loafers, boat mocs, drivers, venetian slip-on loafers, or desert boots. There are many different styles that fall into this category, and factors like where you live, lifestyle, and personal taste will all influence what you chose. For example, a pair of boat shoes might work great for coastal regions, but they won’t be as versatile for those scrambling around the rugged terrain of the Desert South West. Yet all of them are going to showcase an “elevated casual” style that’s a step or two above a pair of athletic sneakers.

 

#5. The Versatile Low Top Sneakers

• adidas Stan Smith Lux – $145 (review here)
• Nike Killshot 2 – $90
• Nike Air Force 1 ’07 – $74.97 w/ FALL25 ($125)
• Vans Premium Authentic 44 Suede Sneakers – $85 (review here)
• Rothy’s RS01 Sneaker – $179 review here

It’s tough to beat a classic pair of low top sneakers. Why low top? They’re easier to wear year round. While high tops are classics, too, they’re a bit harder to wear with shorts in the Summer. Opt for low top sneakers in canvas, suede, leather, or a tech knit fabric in a neutral and versatile color like white or grey. This way, they’ll match a wide variety of outfits regardless of the season.

 

BONUS: The Foul Weather Boots

• L.L. Bean Boots w/ Gore-Tex and Thinsulate – $229
• L.L. Bean 8″ Boots – $149 review here
• Hunter Original Short Insulated Boots – $102.57 ($180)
• Bogs Rancher – $95
• Huckberry All-Weather Duckboots – $75 FINAL ($188)

With climate change in play, mother nature is throwing a lot of wild weather scenarios our way, and a good pair of foul weather boots will help keep the heavy rainfall, puddles of muck, and the cold, fluffy white stuff away from our feet. They’re also a lifesaver when your dang dog decides to have a digging competition in the mud.

About the Author: Adam Terry is a thirtysomething salesman in the heating and manufacturing industry. He enjoys bourbon, boots, sneakers, denim, and working on his dad bod father figure.