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
- Allen Edmonds Park Avenue – $395
- Allen Edmonds Carlyle Oxford – $395
- Banana Republic Italian Leather Cap Toe Oxford – $95ish
- Jack Erwin “Joe” Oxford – $195
- Meermin Cap Toes – $195 …careful, shipping is $15 + you’re on the hook for returns
- Massimo Matteo Oxford Cap Toe – $175
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.
A note on any Allen Edmonds in this post: Check your USPS mailbox. If you got a snail mail catalog from AE, there’s probably a $75 off full price one time use coupon stuck to the back cover.
#2. The Indispensable Brown Brogue
- Allen Edmonds Strand – $395
- Suitsupply Brown Cap Toe Oxfords – $249
- Johnston & Murphy Daley Medallion Toe Oxford – $169
- J. Crew Ludlow Semi-Brogues – $298 often on sale for less
- Allen Edmonds McAllister Wingtip Oxfords – $395
- Aston Grey Wingtip Blucher – $89.99
- Grant Stone LWB Crimson Chromexcel – $330
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
- Rhodes Footwear Dean Boot – $220
- J. Crew Goodyear Welted Kenton Pacer Boots – $248 often on sale for much less
- Original Chippewa 6-Inch Service Utility Boot – $280
- Allen Edmonds Liverpool – $495 shown top of post, center
- Red Wing 6 Inch Moc Toe Boot – $280
- Jack Erwin Reade City Chukkas – $165
- Spier & Mackay Jumper Boot in Brown or Black – $278
- Allen Edmonds Higgins Mill – $425
- Allen Edmonds Dalton Wingtip Boot – $475
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
- Allen Edmonds Sea Island Loafer – $295
- Banana Republic Nyle Suede Buck – $90ish
- Sanders Chukkas – $248 ($298) shown top of post, 4th from left.
- J. Crew Ludlow Suede Penny Loafers – $298
- Clarks Original Desert Boot w/ Crepe Sole – $80 – $130
- Spier & Mackay Burgundy Loafers- $248
- Florsheim Highland Bucks – $114.95
- Banana Republic Dellbrook Italian Leather Loafer – $90ish
- Sebago Crest Dockside Boat Shoes – $50
This is a category that covers many styles. Penny loafers, drivers, desert boots (I know, crossover), bucks, etc. Some of us live in our chukkas, even in summer. Some of us wear our boat shoes year-round. 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 – $80
- BR Nicklas Leather Sneaker – $75ish
- Nike Killshot – $90
- 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.
Shoes shown at the very top of this post are, from L-R: Allen Edmonds Weybridge (discontinued), Dark Brown Allen Edmonds Mackenzie (also discontinued!), Allen Edmonds Liverpool, Sanders x Todd Snyder Suede Chukkas, Good Man Brand Legend (blue accent option seems to be discontinued). A version of this post originally ran in 2016, but has since been updated with current product suggestions.