“How about a ‘The 10 Best Looking Dress Shoes Under $100″ article?”

– Brian from over here.

Hang on now, what is that, a reverse re-raise? The level of money isn’t going up, but the difficulty sure is. Under $200 is absolutely doable. Under $100 and the flock gets culled quick. It can be a challenge, but good if not great looking dress shoes for under a hundred bucks are out there. Just keep the expectations for their durability reasonable (okay, low) and try to go easy on them. Here we go. Just for Brian… and everyone else reading this. Kaboom.

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Black, but not boring. A true oxford closed-lacing brogue with long perfs that sweep all the way back to the heel. Calvin Klein shoes are decent for around $100. The leather seems to hold up, they take a bit of breaking in but eventually get comfortable, and wear reasonably well.

Original Penguin Jaden – $99.95 (ships free with SHIPR )

Penguin shoes can do some work. They have an (almost?) all rubber sole, and their construction doesn’t feel crazy solid in your hands, but they can be found for under a hundred with some consistency. They also have decent style details and good toe shapes. Brown or black at DSW, with what looks to be a lighter tan (or is that just the same brown in different light?) over at LastCall… wait for a sale there and you can get em’ for around $80.

A little better with jeans than a three-piece suit, but they’re incredibly good for fifty bucks. Soft leather that gives, pretty comfortable, and closed lacing. The toe shape is perfect. Sole is synthetic, with a grip rubber insert. A similar derby style longwing is available in black (here’s the difference between derby/blucher and oxford shoes) and a plain derby lace-up is available in cognac.

So the lighter contrast sole certainly pushes these more towards the casual end, and 30% of you may have little to no interested in monk straps, but they’re as inexpensive as monks usually get, and could very well work in a more casual work enviornment or with a summer suit.

Sort of a reverse cap toe thanks to the extra (but not too crazy) stitching on the heel. Sleek with three color options. Ship/returns free via Nordstrom.

Cole Haan can sometimes nail simplicity. But sometimes their near or even over $200 retail price will make you squint. This trio is now well under $100 through flash sale site Rue La La as part of their Final Sale event. And final sale is final. No returns here. No cap or apron toes. Just plain. Big fan of the incredibly simple loafer.

Gotta wait for a sale. And you should. Haven’t seen these in person yet, but sit tight for a 30% off sale that actually includes shoes. Plenty of them exclude shoes and men’s suiting, so… hang out for one of those rare one’s that actually opens up the gates a bit. Ships free. Looks good online… but in-person? And the feel? That’s to be determined. (Note: These might be 30% off tonight during the cardholder after 5 event. 30% off online with BRSUMMER30 between 5pm ET and 11:59pm ET if you use a BR/GAP/ON card.)

Plain Jane. And at just over sixty bucks, don’t expect much other than a simple, sleek shoe that will need to be babied a bit. Don’t drag those feet fellas.

Obligatory. Been getting quite a bit of run here over the last couple weeks. Sabir, out of nowhere, picked them for one of his 5 favorites. And Sabir was recently featured by Johnston & Murphy to help introduce their new McPherson line. Sabir knows his stuff. What’s good for him will probably be good for you too. Ships free with SHIPR.

And speaking of J&M… Alright, so, fudging by a buck-twenty-five on the price limit here, but let’s forgive going over the limit by five quarters since there’s three Cole Haan and three Stafford options up above. Plus, these ship free. Dig around in the couch cushions if you have to. Italian calfskin, a great shape, and the cognac is a dead on, not too orange looking color. The double stitching for the cap toe is also a big plus. Also available in black. Not eligible for the extra 20% off code EXTRA that Lord & Taylor is running right now.

What was missed? $100 is no easy price limit. Leave any other tips on ultra-cheap dress shoes below…