Esquire’s Best New Dress Shoes at “Any” Price

Esquire Style Blog: Fall 2010 Footwear Trends

There’s an argument to be made for spending the extra money on dress shoes.  If you work in a dressed up environment, you’ll probably have a weekly rotation between black and brown laceups, and then maybe a pair of loafers on Fridays.  Your shoes are suffering a lot of pounding, and a lot of wear.  So spending the money will probably be well worth it in the end.

But since when is $225 “affordable”?  That’s the cheapest pair you’ll find on the Esquire Style Blog’s list of best new dress shoes.  The Style Blog on Esquire.com is a recent addition, and it’s terrific.  A daily read for sure.  The list is a nice breakdown of five different styles with five suggested pairs for each… but there’s nothing truly affordable on there.  Click on over to their slideshow and give it a look.  When you’re done with the sticker shock, head back this way for their cheapest suggestions with even lower priced alternatives from us.

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#1 Wingtips:  Esquire – J. Crew Gifford $225 |  Dappered – Cole Haan Garrett $103.95

There’s only about nine different kinds of wingtips, and it all depends on what you want to use them for.  A standard modest go-to for work is the rounded toe, not too sleek, classic wingtips you see above.  Only the Cole Haans on the right cost half as much as the pair from J. Crew.  If you want a super casual bang around pair, you can get those for $60 with free shipping from American Eagle.  Want a lighter brown Italian made higher-fashion stunner?  Try these narrow toed wingtips from Mercanti Fiorentini.  On sale for $130.
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#2 Loafers:  Esquire – Saks 5th Ave. – $298 |  Dappered – Steve Madden Ezee – $50.00

Admittedly totally different, the Esquire pick leans more conservative while the Steve Maddens are certainly more modern.  But if you want modern and plain, to-ta-lly plain (which is hard to find), $50 with free overnight shipping from Endless is tough to beat.  If you want something almost identical in shape and detail to the Esquire picks?  Try the Gant Cage Penny Loafers which made a strong showing in the recent loafer feature.
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#3 Monk Straps:  Esquire – Brooks Brothers $448 | Dappered – Cole Haan Lucarno $180.40

Monkstraps started to form a substantial resurgence around two years ago.  Now they’re in a full blown revival, but finding a pair under $200 is almost impossible.  The option from Cole Haan sneaks in around $180, plus they’re made in Italy.  If you want something sleeker with a double monk, give this Burgundy pair from Mercanti Fiorentini a look.
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#4 Cap Toes:  Esquire – Allen Edmonds $295 | Dappered –  Aldo Crubmliss – $100

It’s tough to argue against the legendary quality of the Made in the Midwest Allen Edmonds, but $300 is just not possible for a lot of guys.  And if you need a pair of dress shoes, a cap toe is a good safe option if you want something more than just a plain toe lace up.  The Aldo Crumbliss is also available in black and taupe.
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#5 Boots:  Esquire – Cole Haan Colton Chukka $228 | Dappered – F. W. Adler Chelsea $120

Desert, Ankle, Chelsea, Rugged, and Extra Dressy.  Those are the five types of boots Esquire runs through.  Finding minimalist versions of all of those for under $150 is a challenge.  For a casual Desert boot, those J. Shoes leather Desert Boots are still available through American Eagle for just $60.  For wingtip styled boots, you’ll have to wait but the back-ordered Urban Outfitters Ritanos look pretty sweet.  And for a plain zip up Chelsea, the above Frank Wright Adler boots have the perfect slim but not razor sharp toe that’ll go with everything.

What do you wear the most of?  And at what price point do shoes get expensive for you?