Online Shopping Picks: Stylish Men’s Dress Shoes

A shoe for every possibility. Don't worry -- the shoes on this list aren't that expensive

A shoe for every possibility. Don’t worry — the shoes on this list aren’t that expensive

Editor’s note: For more online shopping picks covering everything from great brands, gift guides and the best warm-weather blazers and shorts, head here.

As I was preparing this post, I got a question from a reader on the very topic about to be addressed below — what’s a great, versatile (second) set of shoes fit for a business casual environment and beyond? Well, that answer’s coming shortly. Meeting the needs of your everyday life while also having a sharp pair on-hand for seasonal occasions, like holidays or weddings, is part of building and maintaining a well-curated closet (although I doubt many of us have space like the above photo!). So with that in mind, I’ve pulled together some picks below that cover both specific occurrences as well as versatile three and four-season picks with a budget in mind. Let me know your thoughts and reach out with any questions via the Contact page!

The Versatile, Everyday Dress/Casual Shoe: Florsheim Jet Chukka, $135

Take your pick of black or brown, and wear 'em with jeans, chinos or a suit.

Take your pick of black or brown, and wear ’em with jeans, chinos or a suit.

If you already have an affordable dress shoe that can stand in for everyday wear (like the second option on this list), upgrading to something a bit unconventional is certainly one way to go. The Florsheim Jet Chukka has a sleek toe shape, sharp three-eye chukka boot construction and the ability to be worn both with slim chinos, dress trousers or jeans. This style can even be worn with a suit — just ask James Bond. The price is pretty agreeable for an offering from a respected brand, although on the regular dress shoe front, the Mercanti Fiorentini Wingtip Oxford would also be an exceptionally wearable upgrade for just about $15 more. Don’t sleep on something like the Aston Grey Captoe, either, and a slick Chelsea boot would be an alternative style option to look into as well.

The Budget Dress/Casual Option:  JC Penney Stafford Logan Wingtip, $49.99

Fit for weddings, office wear and casual Fridays.

Fit for weddings, office wear and casual Fridays.

This particular style has made a few appearances on this blog, notably in last fall’s budget style series. It’s received surprisingly solid reviews, similar to the much-loved Stafford Wingtip Boot of old. The quality isn’t anywhere near as strong as the Mercanti Fiorientini Oxford discussed above, but in a pinch, it should provide reliable style for the price. The color, while a little bolder than a more versatile dark brown, should work with everything from lightwash jeans to chinos. It’s also available in Black for that same low, low price — and considering these shoes normally retail for almost twice the current price, it could be wise to pick up a pair now.

Nunn Bush

The Upgraded Dress/Casual Option: Jack Erwin Adam Wingtip Oxford, $195

It doesn't get much more classic than a dark brown wingtip at a more premium price.

It doesn’t get much more classic than a dark brown wingtip at a more premium price.

So let’s say you’re in a unique spot — you can’t quite afford a pair of dress shoes from Allen Edmonds (more on those below) but you want a better-quality pair than the ones listed above. Where do you go? Jack Erwin has you covered. Produced in Spain and designed in New York City, the Adam Wingtip Oxford checks every box you might be looking to fill when hunting for a versatile, affordable shoe. The not-too-dark, not-too-light chestnut brown color, a full-grain calfskin leather upper and a pleasing toe shape allow for wear with everything from a suit to denim and a T-shirt if you’re feeling a bit more bold. The same style is also available in a very continental dark brown suede.

The Casual Three-Season ‘Dress’ Shoe: J. Crew Factory Calvert Suede Oxfords, 98

Dark tan suede + a rubber sole = an Oxford that wears like a desert boot.

Dark tan suede + a rubber sole = an Oxford that wears like a desert boot.

Suede is one material that, much like fine leather, fits in just as well during spring & summer as it does during fall. In fact, other than a pair of crisp leather loafers, there might not be a dress shoe more geared toward warm weather than a suede Oxford, like the Calvert from J. Crew Factory. While this pair leans much more casual thanks to a rubber sole, that also makes it a little more versatile. This shoe should wear and feel more like a suede desert boot, making it the perfect lightweight match for a light blue cotton suit and an outdoor wedding, or a pair of lightwash jeans and a short-sleeve henley. Wait for a sale and  they could dip below $70. The Kenton Suede Bucks from J. Crew provide similar summer style for about $100 more.

The ‘Serious Investment’ Dress Shoe: Allen Edmonds Fifth Avenue Captoe Oxfords, $385

American-made. Suit-ready. Five color options available.

American-made. Suit-ready. Five color options available.

By far the dressiest and priciest of the bunch, the Fifth Avenue Captoe Oxford is legendary in the premium footwear market for its made-in-America quality and sharp looks. While the brand has something for everybody, (including equally pricey wingtips), this captoe model has been around for decades and continues to hold its own. Considering the price of this shoe, it can and should be worn in as many ways as possible. The captoe is dressier than a plain old wingtip, but with a pair of slim cuffed denim and an unconstructed blazer, it wouldn’t look too out of place. Picking  up this pair in black would be conservative on the style spectrum, but if you own one pair of black dress shoes, make it these.

When sorting through the world of men’s dress footwear, there are bound to be brands left out. Banana Republic’s Digby Brogue gets an honorable mention nod, as does the absurdly expensive (yet lovely) Brown Plain Toe Blucher from Oak Street Bootmakers. Out of the above picks however, any option should be able to transition seamlessly from day to night, and from outfit to outfit.

Which of the above pairs is on your must-buy list? Are there any brands you would add? Let me know in the comments!

Need a sharp shirt or weekender bag to go along with your new dress shoes? Take advantage of the exclusive offer below from Ernest Alexander, now through July 31. Happy shopping!

$10 Off a purchase of $100 or more; Free Shipping on orders over $200 at Ernest Alexander Enter promo code: STYLEGUIDE10 at checkout. Valid 06-12-2015 through 07-31-2015

Ernest Alexander

Ben Sherman US


  1. […] As far as quality shoe brands are concerned, Singapore is largely a barren wasteland. While establishments like Ed Et Al, Carmina and Septíème Largeur have opened in recent years, the majority of Singapore’s shoe landscape is still dominated by the likes of Hush Puppies and Ecco. There remains a dearth of choice for quality shoes at specific price ranges -for instance, Ed Et Al is the most budget-friendly option, with prices for their (excellent) ready-to-wear pieces starting around $350. [Editor’s note: Check out other budget-friendly dress shoe options here]. […]


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