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
- Banana Republic Italian Leather Cap-Toe Oxford – $95ish
- Allen Edmonds Park Avenue – $395
- Allen Edmonds Carlyle Oxford – $395
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 – $395
- Charles Tyrwhitt Brown Goodyear Welted Oxford – $199
- Johnston & Murphy Conard Cap Toe Oxford – $169
- Suitsupply Brown Cap Toe Oxfords – $299
- Grant Stone LWB Crimson Chromexcel – $350
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. Darker brown will be more versatile, yet lighter brown will be more eye-catching (as shown above with the walnut Allen Edmonds Strand).
#3. The Obligatory Boots
- Allen Edmonds Higgins Mill – $395
- Huckberry Rhodes Dean Boot – $220
- Banana Republic Norman – $90ish
- Clarks Men’s Bushacre 2 Chukkas – $60ish
- Jack Erwin Mason Chukka – $195
- Allen Edmonds Dalton Wingtip Boot – $445
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
- Jack Erwin Suede Penny Loafer – $195
- Florsheim Bucktown Plain Ox – $114.95
- 1901 Stucker Plain Toe Derby- $109.95
- J. Crew Oar Stripe Penny Loafers in Italian Suede – $248
- Banana Republic Dellbrook Italian Leather Loafer – $90ish
- Nordstrom Patrick Driving Moccasin – $114.95
A category that covers many styles (penny loafers, drivers, bucks, etc.) 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.
#5. The Versatile Low Top Sneakers
- adidas Stan Smith – $75
- Banana Republic Nicklas – $75ish
- Nike Killshot – $90 (fine, I give in)
- Superga Cotu Classic – $64
- Good Man Brand Legend Sneaker in White – $198
- 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.