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 wacky/super modern)
#1. The Mandatory Black Oxford
- Jack Erwin “Joe” Oxford – $195
- Massimo Matteo Oxford Cap Toe – $159
- Allen Edmonds Park Avenue – $425
There’s no getting around it; we all need a pair of formal black oxfords. Funerals, job interviews, black tie weddings, and other inevitable life events call for this shoe. Your black oxfords might be the least worn shoe in your closet, but you’ll be happy to have them on hand (and on foot) for those important occasions.
#2. The Indispensable Brown Brogue
- Allen Edmonds Strand – $425
- Cole Haan Harrison Grand Wingtip – $134.90 ($220)
- Charles Tyrwhitt Chocolate Goodyear Welted Oxford Brogue – $199
- Allen Edmonds for Brooks Brothers McAllister – $298 ($428)
- J. Crew Goodyear Welted Ludlow Wingtips – $298
Wingtip, cap-toe, long-wing, balmoral, or blucher. Brogues come in a wide variety of styles and levels of formality. Choose one that fits your weekly lifestyle best. Brown brogues can be worn with anything from a suit, to a pair of dark, well fitting denim, from khakis to flannel trousers.
#3. The Obligatory Boots
- Allen Edmonds Higgins Mill – $395
- DSW Aston Grey Chelsea Boot – $109.99
- Clarks Men’s Bushacre 2 Chukkas – $65
- J. Crew Kenton Plain-Toe Boots – $248
- Jack Erwin James Chukka – $220
- Loake 1880 Mitchum Suede Chelsea Boots – $280
- Allen Edmonds Dalton Wingtip Boot – $495
Boots are perfect for those days when the weather is rough, and lesser weaker shoes let the elements nip at your delicate, sensitive mankles. Office warriors can add a touch of rebellion to their work outfit by swapping the oxford shoes for a pair of dress boots. Life travelers can treat their ankles to a pair of suede chukkas. Londoners and Australian businessmen can wear black Chelsea Boots everywhere. Yes, everywhere.
#4. The Essential Casual Shoes
- J. Crew Goodyear Welted Ludlow Penny Loafers – $288
- H&M Premium Quality Suede Bucks – $79.99
- Jack Erwin Parker Driving Loafer – $115
- Banana Republic Dellbrook Italian Leather Loafer – $88.80 (when 40% off)
- Florsheim Bucktown Plain Ox – $114.95
These are shoes for days when we don’t want to dress to the nines. We want something informal and comfortable, and we want to look damn fine in our leisure. Now be a dear and hand me my Manhattan.
#5. The Versatile Low Top Sneakers
- adidas Stan Smith – $75
- Banana Republic Nicklas – $76.80 (when 40% off)
- Superga Cotu Classic – $62
- Sperry Top-Sider Striper LL CVO – $59.95
For when you’re at your most casual, yet not at the gym, it’s tough to beat a pair of classic low top kicks. Why low top? High tops are great and all, but they’re pretty tough to wear with shorts in the summer. Low top, canvas, suede, or leather sneakers can be worn year round with a variety of outfits. Get them in white or a neutral shade and they’ll go with everything.
A version of this post originally ran in 2016, but has since been updated with current product suggestions.
Shoes shown at the top of this post: Allen Edmonds Weybridge (discontinued), Allen Edmonds Fairfax, JC Penney Stafford Gunner Boot (discontinued), Banana Republic Loafers from a few years back, and the Superga Cotu Classic.