10 pairs of casual shoes – Dressed down but not out

From the Mailbag:  Enough with the dress shoes.  What about casual stuff?

We’ve seen enough work and dress shoes, God knows I have a brown pair that looks great.  But seeing some casual shoes that you could wear with jeans would be helpful!  Thanks!

– Freddy
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God knows Freddy’s brown pair looks great?  “I’m A God.  Not THE God.  I don’t think.”  Now many of us in the not-God-camp (it’s a big camp, lots of leatherworking tents) want to know what Freddy’s dress shoes look like.  Glad they’re working out for him and the almighty approves.  He’s certainly onto something.  Guy’s aren’t always in dress shoes.  And sometimes a heavier boot doesn’t look quite right with a t-shirt and jeans.  10 pairs follow for those times when you’re real casual, but not sloppy.
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Seavees  Army Issue High Tops in Navy or Natural, & Woodland or Slate- $65.99 ($108)

Never thought a pair of classic looking American style sneakers would ever generate compliments, but these do.  They look just different enough.  Design is inspired by the sneakers that soldiers at San Bernardino county’s Fort Irwin wore back in the 60s.  The toe cap is ribbed, and the footbed has more of a curve to it.  The woodland or slate option come with a suede tonal stripe at the heel and the tongue is suede as well.  Genuine gum rubber outsole too.  Chuck Taylors are great.  These have more curb appeal.

NOTE: Looks like DSW has the slate-grey pair for $59.95 and free shipping if you join their email list and use SHIPR.

 

The Boatshoe Chukka Hybrid Thing: Sebago Beacon – $116 w/code PRES ($135-$145)

Not cheap, but some guys swear by these things.  They’re boots, but not really.  They sort of look like boat shoes, but they ain’t those either.  They’re a goofy blend that feels perfect on a Saturday or Sunday morning when you’re out of the house but in no particular rush.  Rawhide laces, good thick leather, and with the code PRES you get 20% off at Macy’s and free shipping.  They’re tough to find on sale with a good variety of sizes.  So it might take some hunting around if you want them for less.  Somewhat similar and cheaper: L.L. Bean Signature’s Handsewn Ranger Moc.

 

Gorilla USA Suede Lace-up – $119.40 ($199) | Suede Chukka – $129.00 ($199)

Part of LastCall.com’s current 40% off one item sale.  Made in the USA and built extremely well.  Hard not to like grey suede once you put a pair of shoes made out of it on your feet.  Limited sizes in the boots.  Boots also available in brown or navy.

 

Not too preppy boat shoes: Sperry Top-Sider Original – $89.95

Boat shoes are inherently preppy.  They’re also understandably seen as a warm weather shoe (not a lot of boating going on once the weather starts getting cold).  But if you stick with earthtones instead of bright or highly contrasting colors, they end up just looking like… a shoe.  These in suede are about as close to slippers as it gets without looking sloppy.

 

Billy Reid for K-Swiss Venice Surf & Court – $39.99 ($85)

“…this impossible-to-find collector’s item is available in extremely limited quantities”… Or not.  They’re on sale for more than half off after all.  Down to forty bucks now, and could dip stupid cheap with the next extra-30% off sale.  Unmistakably casual, but Billy Reid‘s details like  that washed black exterior, the stripes, the rope laces and brass d-rings… all add up to make them anything but any old pair of $40 sneakers.

 

Clark’s Desert Boots – $77.35 ($120)

Undeniably classic.  Yes they’re a boot, but unlike some big Chippewa numbers, these are lightweight enough visually that they wouldn’t look too out of place with just a t-shirt or polo on top.  Three color options (pictured would be the beeswax leather) over at Piperlime where they’re on sale for just under $100, plus they ship and return free.  UPDATE:  Screw the piperline route… they sell for the high $70s at Amazon.  Updated above.  Many thanks to Farhan for that mention in the comments.

 

Driving Loafers: Cole Haan Howland in Black or Tan – $99.90 ($148)

If you’re not the boat shoe type, you might be the driver type.  Plenty can’t get over that rear heel grip, but that’s there to help give your foot some grip and a place to rest/rock back and forth on when driving your fancy sports car (or, whatever you have that’s fun to drive that requires some pedal action).  Most are obscenely comfortable as long as you’re not walking great distances or standing for long periods of time in them.  These things are usually more lightweight and slim compared to other more supportive types of footwear.  They also look terrific in suede.  Feel free to read this appreciation of drivers over here.

 

Dressed Down Monks: Brooks Brothers Desert Boot – $198 | AE Lubbock – $199 ($295)

All right, so these aren’t going to neccessarily look perfect with just a t-shirt and jeans, but they’re real casual for a monk strap.  The Brooks Brothers boots look like they’re here to stay, since they’ve been around for at least a few seasons and tend to go on sale every so often.  The AE Lubbock is part of their Rough collection, and it’s now almost $100 off.

Any additions?  When you get through the door at the end of the day, what’s your go-to pair for the Mr. Rogers transition?  Or are you usually in dressed up stuff because you’ve spent the money on them?  Do you usually move to heavier boots?  Leave it all in the comments below.