II. Casual/In-between Shoes Lots of guys focus on sneakers for casual shoes, but in almost every case, they’d be better off moving up into this category. These are shoes that are still casual (almost all of them would look great with jeans, rolled-up chinos and shorts) but look more mature than sneakers. Again, opt for classic styles with a history – it’s harder to go wrong with something that’s been around, virtually unchanged, for 75-100 years. These’ll generally cost more than sneakers, but not as much as well-made dress shoes. In many cases, they’re resoleable (like dress shoes), which extends their life dramatically.

• Loafers – Not dress shoes – they’re for loafing. Bass makes affordable loafers (and has a long history with this type of shoe), Rancourt and Oak Street make mid-range models, and shell cordovan Alden Leisure Handsewns are the holy grail. Types include full-strap 
  

  , pinch-penny 

  
  
  

  , beefroll 

  

  , tassel 

  

  and venetian loafers 

  

  . I love beefroll loafers, but that’s a personal preference.

• Bucks – in white nubuck or tan suede, with a red brick sole. Classic spring/summer footwear, perfectly appropriate with jeans, go-to-hell chinos or shorts (sockless). To wear white bucks the most traditional way, you’ve got to go all-in preppy or pick up a seersucker suit 
  

  . To use an oxymoron, white bucks are the most traditional go-to-hell shoes 

  

  . Tan bucks are a little easier to wear, imo – they look great with jeans, for example. There are brighter-colored options, but not until you have other footwear basics covered.

• Desert boots/chukkas – Clarks Desert Boots (CDBs) get mocked as the MFA-hivemind item, but the fact of the matter is that they’re a pretty good in-between option. Beeswax leather and taupe or sand suede are the most versatile choices. Lots of other companies make chukka boots too – from low-quality $40 pairs at Kohls to $700 shell cordovan Aldens 
  

  .

• Blucher mocs/canoe mocs/camp mocs – A more grown-up alternative to boat shoes. These generally have a charcoal or red sole, 1-4 eyelets, and no collar lacing. GQ tells you why they’re classics. 
  

  LL Bean makes affordable pairs, Quoddy and Yuketen make higher-end pairs (in Maine). I’ve beat the hell out of this pair of Quoddy Canoe Mocs in chromexcel 

  

  for three straight summers and they just keep looking better and better. IMO, that’s the advantage of paying for quality up front. I’m biased, because these are my favorite casual shoes. Here are some other photos – Blue chromexcel Oak Streets on Simplethreads, LL Bean 

  

  , LL Bean Signature 

  

  , Sebago Campsides 

  

  , Oak Streets in navy suede with red brick sole. 

  
• Boat shoes – Like desert boots, these probably don’t need an introduction. Wear Sperry Top-sider A/Os in Sahara without socks and you’ll look seven guys out of ten in the summer (for good or ill). If you want to go higher-end, Sperry has done some designer collaborations (Band of Outsiders, recently) and shoemakers like Alden, Allen Edmonds, Quoddy and Russell Moccasin all make boat shoes.
• Avoid – Sneaker/dress shoe hybrids like the ones from Sketchers, Rockport and Clarks. You know what I’m referring to. 
  

  They’re overdetailed, overcomplicated and overpriced, and they’re invariably worn by guys who think they’re stealthily getting away with wearing sneakers when dress shoes are required. There are so many better options for in-between shoes that there is literally no excuse to buy these.