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The 10 Best Looking Dress Shoes Under $100

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“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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Calvin Klein Glendon – $99.50 ($140.00)
Ships & returns free through Piperlime.

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)
$99 through DSW, or cheaper through LastCall when on sale.

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.

 

Stafford Wingtip Oxfords – $50.00
You'd never know they were only $50.

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.

 

ASOS Monk Strap – $95.67
Sub $100 monks are a rare thing.

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.

 

Aldo Lehane – $69.90 ($99.95)
Dark brown and black also on sale.

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 Air Jefferson Lace up, Loafer, & Air Samuel Lace up – $69.90 – $74.90
No returns on these.

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.

 

Banana Republic Digby Leather Brogue – $140 (but $98 when 30% off)
New. Hopes are high.

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.)

 

ASOS Lace-Up Derby – $60.88
Well ain't that the shoeiest shoe you've ever shoed.

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.

 

Giorgio Brutini Medallion Cap Toe Oxford – $69.95
They had to make an appearance.

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.

 

Johnston & Murphy Larsey Cap Toe – $101.25 ($135)
Ships free thanks to being over $99.

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…

Comments

  1. What was missed?  The obvious, of course:  thrift!  I added florsheim imperial and allen edmonds longwings, J&M cap-toes, allen edmonds split-toes, and Jos A Bank saddle shoes to my wardrobe in the past 6 months, all for less than $100 total.

    Good list, though.  Those stafford wingtips look great in the pics.  I’m kinda stocked right now, or I’d try ’em out.

  2. In my experience Stafford Wingtip Oxfords aren’t able to be shined well.

  4. I have some personal experience with the ASOS monks.  Do not waste your money.  They are incredibly thin.  Probably the cheapest made shoes I’ve run across in a long while.  I sent them back before even trying them on.

  6. I went the Florsheim outlet route and got their Lexington cap toes in burgundy for $80. The quality is what you’d expect for less than $100 (see above) but this shape to me is perfectly average or averagely perfect. Just right, in other words. 

    I happen to catch a sale and got a second pair half off: $40 for black Canfields. They are of the Imperial line and are definitely a notch up.

    $120 for two pairs of dress shoes, and as little as I wear them, this last for a long, long time.

  8. I have florsheim Imperials that I picked up at Nordy rack and they are passable for what little $ I paid.
    Avoid Cole H at all costs.
    Ridiculously overpriced with laughably low quality – My Air Colton saddles looked like they had been worn 100 times after 10 wearings.
    Summed up by my girlfriend looking at them on my feet and asking: “Since when did you start shopping at Aldo”?

    Do NOT embarrass yourself or your wallet.

  9. I’m not usually a fan of anything of the “wingtip” variety, but the Stafford Wingtip Oxford looks pretty solid with jeans. Might look even better as a dress boot.

  10. Love this list. Usually the shoe lists on this site are overcrowded with shoes covered brogueing, wingtips, and cap toes. Good to finally see a substantial representation of clean plain-toe shoes for once!

  11. Perpetually thwarted by companies that discriminate against clown feet, I’m always in the market for good shoes in size 14 that are a good value-Something between full priced Allen Edmonds and the kind of crap you’re lucky to get a solid month out of.  Anyone particularly good at navigating the very unimpressive selection?

  12. Ebay as well.  I found a pair of black AE McAllisters for $30 and are having them recrafted now.  I’ll get what amounts to a practically brand new pair of AEs for less than half the retail price.

  13. The most important thing when buying (relatively) cheap shoes that happen to have leather soles is to go to a cobbler and have ‘sole savers’ put on before you wear them the first time.  The soles on shoes like this will not be built to last, but for around $20 or so, you’ll get much more life out of them.

  14. Here’s the problem with under $100 dress shoes: you’re paying under $100 for, really, a couple wears before they crease crack and start to look terrible. I know it’s hard bringing yourself to pay a nice amount of change for shoes, but some things just require that extra money. If you’re going to buy these, it should be on an emergency basis knowing that you’ll be paying to do it again pretty quickly. These are disposable shoes.

    I truly believe that shoe purchasing should be a considered and planned purchase. I’m not talking $600 a pair here, but you should think about having a high quality pair of black oxfords in your arsenal, even if you don’t have an upcoming event to wear them to. It’s just something you should plan for, long term. Their style doesn’t change, they’ll never look out of date, and it’s one purchase you can make and say “there, I’m done with that.” 

    Waiting for Brooks Bros. to have a sale on shoes and then being ready to act is a great way to go about this. But spending

  15. sooo cole haan is not a good shoe? i’m ready to pull the trigger on them since i need new black dress shoes but hesitating after some reviews on their wear and tear rate.

  16. Heard this argument plenty before.  And there are two camps: One camp is on board with you, and the other… just hasn’t had that experience.

    Wearing Allen Edmonds right now, and I love the absolute hell out of them.  That said, I’ve had plenty of good luck with shoes that cost under $100.  The fact that someone asked for the list (and there was an email from someone else too as well as the comment) is proof that there’s a good chunk out there that have a budget which tops out at $100.

    You might think a shoe looks “terrible” after a few wears, but I’ve got creases in my new AEs after a few days.  They still look great to me.

  17. Lots of guys like to bag on them in part because their starting retail price seems so high.  They’re owned by Nike, they’re everywhere, and they’re a bit of the Nickelback of the shoe world.

  19. Not a good shoe at $150+ but at the $70 up there? I think they’re passable. IME they run a little narrow, just as a note.

  20. The quality of Cole Haan has gone way down hill. My pair from 1999 held up amazing (still wear); the pair I got in 2009 are laughably cheap material.  I bought some AEs on sale last year (same price) to replace them, they are built extremely well. 

  22. +1.  I love my Florsheim Lexington cap toes.  I think they retail for 100-110 but can be had cheaper as Rod mentioned.  Lots of people don’t like Floresheims but I have worn mine for years and have been a great deal for the money.

    I actually just replaced them with AE Fifth Avenues, but will still wear my florsheims a lot out at bars or other places where I worry about them getting scuffed

  24. I agree with Chris for those shoes that are going to form the backbone of your closet.  That being said, I personally like to experiment with different types of shoes.  Do I like a monkstrap? How about a odd color? What about something to be used on rainy days so you don’t mess up your good shoes? With shoes that may only be worn rarely, but yet serve a particular purpose or go with a particular outfit, I think it is worth trying something cheap before you commit to something expensive.  

    For instance, I personally disdain black shoes.  I have one pair of black loafers, but I wanted something with some laces and some brogueing, just in case a situation arises where I need to wear black, but don’t want to wear loafers.  I purchased a pair of Nunn Bush black wingtips, shined them up, and they look decent.  Not amazing, but decent. Will certainly pass for that rare occasion I wear them.

    One thing I would suggest for people trying to pass these shoes off as regular, everyday shoes (and by that I don’t mean wear them everyday, that is a no-no), is learn how to shine your own shoes.  A well-shined shoe (we’re talking taking a few hours to put down a solid base and then 20 or so minutes a month to keep it up, not that 10 minute thing you get at the mall) will look impressive in, what I’m sorry to say, is a world where you will most often see even expensive shoes in need of a shining.  

    Once you know you love a particular style and want to get a pair that will last you, hopefully, the rest of your life, get some AEs or something of similar quality.  If you pick something timeless that you know you will wear, you will never regret it.  What you will regret is spending $300 on a pair of shoes that never see the outside of your closet.  

  25. Here is a picture of my Nunn Bush shoes. 

    [URL=http://imageshack.us/photo/my-images/585/nunn.jpg/][IMG]http://img585.imageshack.us/img585/7230/nunn.jpg[/IMG][/URL]Hope it works.  I got them for $12 at goodwill in need of a good shining.  Still have  a little to go on the toe box, but you can see what I am headed for at least.  

    $70 new at zappos:
    http://www.zappos.com/nunn-bush-kingsbridge-black-smooth-leather 

  26. I almost snagged a pair of Aston Grey single-strap monks from DSW yesterday. They were on sale for %30 off of their normal price, which was $90. $63 was very tempting for those. They seemed to fit great, at a 1/2 size under my norm of a 12. Good thing, as they only had an 11.5 for me to get. However, I put them back, hoping to find them on their clearance rack in the back for even cheaper. I’ll probably regret that soon.
    http://www.dsw.com/shoe/aston+grey+astor+monk+slip-on?prodId=207611

  30. I’m an 11.5 D US in Allen Edmonds, and fit into an 11 D on this pair. You can easily pick them up in store, though, as they are pretty much always in stock.

  31. Really? I checked my area and they the Staffod Wingtips are unavailable in all 5 of the Jc pennys around me. I guess I’ll just have to wait until they restock.

  32. Very humbled to see this post. I heard your ‘Kaboom!’ loud and clear. Perhaps one day I’ll be blessed enough to feel comfortable with the ‘The 10 Best Looking Dress Shoes under $200’ articles, but until then, this will be my one and only guide. Thanks, Joe.

  33. I have the Original Penguin’s in black that I picked up during one of the recent tiered sales that DSW has. I only wear them once or twice a week but they are holding up nicely and are surprisingly very comfortable.

  35. Nice picks.  Only one loafer though?  I’ve been looking for a nice high vamp penny in brown but haven’t had any luck, was hoping to see something here….Any recs anyone?

  36. I just got those penguins at DSW for $40. They were on sale for 40 percent off plus I had a 20% off coup. 

  37. Can someone with Aldo shoes post pictures of a pair that you have worn with some degree of regularity? I bought similar shoes to the above (cognac ‘digmann’ in store, whoops), and know they’re supposed to be crappy shoes, but I also have not a single pair of oxfords to my name. Interviews are looming! Do I keep these things or take them back

  39. I am not a big baller, but personally, I would never compromise shoe quality. I’ll rather wait and save and go with the best I can afford, as long as it fits and it has to be within the realm of my lifestyle and needs. I have 4-5 shoes that are over 20+ years old..So there you have it, cry once and be happy