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

Style Suggestion: The Summer Wedding

Trying to keep cool and stay stylish. Unconstructed navy blazer by J. Crew.  Vintage red floral pocket square by General Knot. White dress shirt by Combat Gent. Chambray trousers by American Apparel. Brown leather loafers by Bass. Watch by Sturhling. Glasses by Warby Parker.

Trying to keep cool and stay stylish. Unconstructed navy blazer by J. Crew. Vintage red floral pocket square by General Knot. White dress shirt by Combat Gent. Chambray trousers by American Apparel. Brown leather loafers by Bass. Watch by Sturhling. Glasses by Warby Parker.

With the passing of Memorial Day weekend and a quick couple weeks into June, summer wedding season is here in earnest. If you haven’t had the pleasure of attending a summer wedding yet, I would bet you probably have one in the near future. Picking up something sharp, stylish and fitting for the occasion on a budget is a tricky balance to strike. I had the chance to put my packing skills to the test and dress well at the  same time (or try to do so) as I headed to a family wedding in Charleston, South Carolina this weekend (home of my friends at Brothers and Craft, as it were). The evening was lovely  — a wedding and an evening on the water with family is always incredibly special. I myself tried to strike a balance between keeping cool and staying stylish. Ditching the tie and opting for a lightweight blazer and some tailored (but not overly slim) trousers in a super-breathable fabric helped me at least attempt to do that — that’s a tall task when it’s 90-plus degrees out. Some suggestions to help you handle any wedding situation in the months ahead follow below! (Editor’s note: Be sure to check out the bottom of the post for a special discount offer on dressy summer wedding gear from Ernest Alexander for TSG readers!).

The Suit: J. Crew Factory Voyager Suit — $376

A versatile shade of grey with fabric that can stand up to just about anything.

A versatile shade of grey with fabric that can stand up to just about anything.

Now, not every wedding will necessarily require or call for a suit (see the above photo as proof). But if you do have to pick up a suit for the occasion, it’s a wise bet to grab something in a versatile color (like the medium grey option seen here) or the dark navy pairing available through the J. Crew Factory site — that way, the suit can be worn year-round. The fact that this fabric is crease-resistant means that you could even wear it while traveling. If only a blazer need be worn at the wedding in question, picking up something in a vibrant color on the cheap (like this Combat Gent Travel Jacket) would be the way to go (pair it with some crisp khaki chinos for style outside the summer, too). And even if things get as laidback as a polo and chinos (for a beach wedding, perhaps), the suit trousers or jacket could act as separates.

Ben Sherman US

The Dress Shirt: Combat Gent Endurance Shirt — $35

A white shirt that performs much like its name would  imply.

A white shirt that performs much like its name would imply.

Take it from someone who test-drove this shirt in temperatures pushing 100 degrees — when it’s hot out, you want something that’ll wick away sweat and still look crisp. Even if the wedding is indoors, a fabric like this will help you out big-time when moving around outside.The collar will stand up amply without a tie if the wedding leans more casual. And similar to the rest of the brand’s offerings,  it’s exceptionally affordable and performs well for the price — a very agreeable one, at that. You could also opt for a similarly polished shirt from Mizzen + Main, who’s picking up steam as of late with performance-minded dress shirts (among other offerings).

The Shoes: JC Penney Logan Wingtip — $49.99

These shoes also made an appearance in last year's budget style series, and for good reason.

These shoes also made an appearance in last year’s budget style series, and for good reason.

For those on an extreme budget (and if you’re having to buy the suit in one go as well), picking up a dirt cheap pair of surprisingly reliable wingtips  is one way to stand out from the crowd of black shoes likely to be there while also saving a good amount of money (loafers could also accomplish this in truly hot weather). Wingtips are the type of shoe that can work with a full suit and tie or a blazer and chinos — plus nearly any other outfit you can think of throughout the year. While this pair might not be exceptionally durable, they should more than do the job in a pinch (as would some simple suede Derbys from a brand like H&M). Don’t forget about brands like Florsheim, who makes one heck of a sharp dress chukka if you want to switch up your style even further.

The Accessories: The Tie Bar White Pocket Square and Navy Knit Tie — $35

Two items that can work anywhere, anytime -- especially in the summer.

Two items that can work anywhere, anytime — especially in the summer.

Keeping the focus on buying for versatility and affordability, The Tie Bar is still one of the best bets for your money out there as far as accessories go. Yes, those prices have increased — but when you consider the fact that some retailers sell pocket squares on their own for more than the price of the ever-versatile navy knit and white cotton combo seen here, it doesn’t seem so bad. Both those pieces will stand on their own, especially with the medium-grey suit seen above, as well as with a navy option (don’t forget about a summertime staple, the khaki suit). As far as other accessories go, this depends on how much you’re willing to push the boundaries of style — but you could pair wingtips or loafers with no-show socks and a rolled cuff for a cooler breeze (particularly appropriate with loafers), or opt for a punchier patterned pair.

The Rest: J. Crew Braided Leather Belt — $49.50 + Timex Easy Reader Brown Leather Watch — $38.96

Two more casual items that would absolutely work in the summer months -- and beyond.

Two more casual items that would absolutely work in the summer months — and beyond.

With the shade of shoes shown above, it’ll be a little trickier to match both your shoe and belt leathers. But because summer weddings overall do tend to be more casual, a braided leather belt fits right in (H&M is among retailers stocking cheaper options, by the way). The belt’s more expensive than the watch, yes, but this timepiece makes up for it with a textured brown leather strap that considerably dresses up the plainer dial while also meshing nicely with the color of the belt and the shoes. It’s the type of leather that would also work with brown leather loafers.

So that closes the books on this summer wedding style suggestion — making use of items you already own, like a trusty navy blazer or some sturdy chinos can help offset the need to buy all-new gear for a summer wedding. And reaching for affordable style staples makes a lot of sense too and can help ease your wallet through the process. Feel free to let me know what you’ll be packing and wearing at any upcoming summer weddings!

And for those of you who do need some stylish garb for the summer, check out the exclusive promo opportunity below!

$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

Shopping on a Budget: An Updated Men’s Style Starter Kit, Part 3

While getting dressed casually on a budget can be done relatively inexpensively, adding dressier items into the mix makes things trickier in terms of price. Parts 1 and 2 in this men’s style budget recap (which you can see here) tackled just how to revamp your downtime wardrobe in a versatile manner, and Part 3 will set out to do the same. However, this time around, we’re diving into the best places to go for dressier items — dress shoes and dress shirt or two, along with ties and suits. Later on, we’ll wrap things up with other accessories, including watches, belts and socks. For now, suit up on a budget below!

The Shoes: JC Penney

A low price for a versatile shoe in a versatile shade.

A low price for a versatile shoe in a versatile shade.

While JC Penney’s dress shoes won’t win any awards from shoe snobs any time soon, don’t be so quick to turn away from this pair. While it’s a more casual-leaning wingtip shoe (which some would say makes it harder to wear with suits), a lot of us don’t seem to have jobs that require a suit every day of the week. And in those instances, it’ll work just fine. If you have the capital to invest in a higher-quality shoe (even something from the Mercanti Fiorentini line at DSW would work), go for it. But these shoes provide a similar look for a much lower price. On top of that, when worn as part of a rotation throughout the year and when mixing in other business-casual styles, these shoes should hold up alright for the price. Reviews have been largely positive, another plus for these shoes — and it’s worth noting they can drop down to about $50 when on-sale. They’ll also work with jeans and chinos alike (for more on budget alternatives for those styles, check out Part 1 in this series). On top of that, this pair is available in multiple shades, including the versatile dark brown (which would even work with a charcoal suit or pants).

TOTAL: $50

The Dress Shirts: J. Crew Factory

Staple c

Staple colors at terrific prices.

Quality can be hard to maintain when delivering dress shirts at a discounted price, but J. Crew Factory meets that challenge. Unlike other brands (such as Express), J. Crew Factory’s shirts seem more consistently on-sale, especially if you can get into a store during a promotion (currently, one shirt will set you back about $43). Available in staple colors like white and light blue — two shades that go with practically any suit-and-tie combination you can think of — their dress shirt offerings also include stripes, prints and other patterns. And their quality, while a step down from J. Crew, is on-point with similar budget brands. Starting out with two of these in your basic colors expands upon an already solid casual wardrobe. Don’t forget that these shirts, despite the ‘dress shirt’ title, can be worn under v-neck sweaters or cardigans alongside jeans, too.

TOTAL: About $86

The Tie/Pocket Square: The Tie Bar

Two wardrobe staples well-suited for more casual or dressy wear.

Two wardrobe staples well-suited for more casual or dressy wear.

There’s a reason GQ uses products from The Tie Bar month after month after month in its shoots. For a fraction of the price of other high-end ties, The Tie Bar delivers the same styling and pretty darn good quality, to boot. While the sheer array of fabric choices and variety of ties on their website is overwhelming at times, the brand makes terrific ties at terrific prices. And for all the wide varieties they stock (including a dizzying 62 pages of bow ties), they do the essentials very well, too. If you had to start with only one or two ties to pair with the restock you’ve already taken care of, reaching for either a navy or a black knit tie would be one great way to go. The silk knit hits on both casual and dressier fronts —either color goes with virtually any outfit combination from chinos to jeans (although a navy knit tie should be worn with brown accessories), and there’s a reason James Bond wore a black knit tie. Additionally, the price makes it easy to throw one of these in your cart along with other accessories — like a white cotton pocket square, an all-season essential that’s the perfect finishing touch to a blazer or suit. So, if you start with one go-anywhere, do-anything tie (like the navy knit) and toss in a versatile pocket square, you’re looking at a price that hits the sweet spot.

TOTAL: $23

The Suit: J. Crew Factory

In a classic color like navy, this J. Crew Factory suit is worth the extra money.

In a classic color like navy, this J. Crew Factory suit is worth the extra money.

When you need a suit on a tight budget but prefer a step up in quality, turning back to J. Crew Factory is once again the way to go. Their line of Thompson suiting has drawn high praise across the blogosphere and with customers for exceptional fit and quality for a budget-tier suit. This year’s run of suits appears to be no exception. The brand doesn’t do anything overly fancy — standard double-vent suits in worsted wool that could work in a pinch in nearly any season. The color offerings are the perfect starter’s set for a suit — charcoal and navy options, along with some flannel fabrics mixed in and a chino option for the warmer months. If you’re just jumping into the suit game, either of those staple colors (navy or charcoal) would be a great look — their neutrality, while not flashy, provides so many options for mixing and matching. The pants, crucially, come in a slim-fit option. Admittedly, the line doesn’t have the pedigree of J. Crew’s Ludlow suits, yet you get nearly a dead look-alike for the price. Take that navy suit, throw it together with a light blue dress shirt, navy knit tie and white pocket square as discussed above, and you have an office-ready outfit While the price, even on discount, might cause some eyes to pop, this suit is a definite upgrade from a standard department store offering, or a more affordable option, like Express. On top of that, the suit brings versatility with it. In a tight spot, the jacket can function as a blazer with chinos, for example, while the pants can be worn on their own with other dressier offerings.

TOTAL: $316

Editor’s note: This rundown is pretty focused on the color blue, no? Fear not — shake things up with some wild socks

So, the total for today’s dress essentials comes to about $475 — quite a lot of money in comparison to last year’s men’s style starter kit.  However, these items are the basics of a dressier wardrobe, yet can do so much more. Break up the shirts and knit ties with sweaters and jeans, wear the wingtip oxfords with chinos and suit pants, and use the jacket as a blazer when needed. The color palette of most of these offerings, as well, can be mixed and matched with plenty of other choices.  Plus, paying a bit more money for a few basics up front can ensure you get more use out of these items than you would when picking them up from a cheaper retailer. Keeping these essentials in mind will save your pocketbook more in the long run. After all, building great style on a budget is fun, but having more money left over to go out and wear those clothes is infinitely better.

Do you have any go-to’s for dress essentials on a budget? Alternate picks? Leave it all below! 

 

Shopping on a Budget: An Updated Men’s Style Starter Kit, Part 1

The process of building great style on a budget is incredibly tricky and only getting trickier, as it seems retail prices are on the up-and-up everywhere (especially at mainstay stores like J. Crew). Budget style has been a frequent focus of this blog (check out the Starter Style series for more on that), but there’s always room for improvements and updates. Last year, I covered how to build a start-up wardrobe for under $250; think of this series as a revamp to that, with a slightly wider selection and some new categories. This first part will tackle the basics you need on your legs — chinos, jeans and shoes, namely. Next week, we’ll tackle casual knits (tees and henleys), casual and dress shirts and sweaters, and then wrap up with accessories. Without further ado, dive in below to check out how you can start to update your wardrobe for as little green as possible. 

The Shoes: Versatile Brown Chukka Boots

The ever-versatile brown chukka boot.

The ever-versatile brown chukka boot.

Starting from the ground up, if you had to go with, let’s say, just one pair of shoes to start, it’s hard to go wrong with a versatile chukka boot (this model’s out of stock right now, but a similar option can be found here for only about $5 more). With just the right amount of sleek styling and in with a build that’s adaptable to both business casual situations and more casual-rugged outfits, this particular chukka pays homage to the more laidback Clarks desert boot while looking more polished. It just looks more natural to wear this with jeans off-duty than a regular, low-cut dress shoe, as well. And in a rich brown, this shoe works across all seasons and can even stand up to harsher fall and winter weather. When considering adding in a pair of casual sneakers on a serious budget, look for a lightweight, neutral plimsoll, like these from Urban Outfitters. Lastly, if you do happen to need plain old dress shoes, this pair from JC Penney should get the job done in a pinch.

TOTAL: About $125

The Jeans: Levi’s Dark Denim 

A timeless original.

A timeless original.

When it comes to buying jeans, it’s really tough to beat a classic original like Levi’s. For about $50 right now through the Levi’s website, you can pick up a pair of great-fitting, dark denim — a wardrobe staple that can be almost worn anytime, anywhere. In both business-casual settings and in any casual situation, a dark, slim pair — like the Levi’s 513 — won’t steer you wrong. At such a low price, it’s much more cost-effective to pick up a few pairs than paying more for one expensive denim. Durability isn’t sacrificed to an extreme degree, either. On a personal note, a pair of Levi’s 508’s (now the 522 model) have held up for well over two years with heavy wear — and that’s just one example of their durability.

TOTAL: $50

The ‘Other’ Pants: Slim Tan Chinos 

In a versatile, all-season shade of tan.

In a versatile, all-season shade of tan.

Unfortunately, dark denim does need to be put aside for more formal business and office settings, and it’s also nice to have different pairs of versatile pants for other situations, too. That’s where a pair (or multiple pairs) of slim chinos can fill in. They look more office-ready than dark denim on some occasions while still staying budget-friendly. Most importantly, don’t make the mistake of thinking the chino can’t be worn casually, either — check out great ways to style them over here at Effortless Gent, as written by yours truly. Uniqlo’s offering a tan chino right now for an outstandingly low price — know that sizes and colors are limited now, but keep an eye on their site for more of these.

TOTAL: About $30 

So, starting with just the basic styles here and building off of those, you’re looking at about $200 in total (keep in mind that last year’s style breakdown set the overall budget at $250). However, that’s spending on three pieces that can work practically anywhere, and do so for a long time. And, when dropping more on certain items, it’s wise to know when to cut back in other areas. Look for more next week, when we’ll tackle a full range of shirting options for the stylish guy on a budget.

Any suggestions for alternatives to these styles? Favorite budget picks for jeans, chinos or shoes?

Fall Style Suggestion: JCP Stafford Wingtip Boots

UPDATE: Before you get into the main part of this post, know that the Stafford Camlin boots are going fast. Like, way fast. They might not be around many JCP stores for much longer, in fact, according to this post from Dappered.com. But the suggestion they offer there, while different in looks and quality, could work in much the same way as the Stafford Camlins.

As temperatures dip and the sun fades across the horizon (a pretty bleak picture, no?), most of us are heading toward fall and…brace yourself for it… winter. That means snow, cold temperatures and several quite noticeable wardrobe changes. If you’re fortunate enough to live in a place without significant temperature deviation, you might be in luck, and you can keep those summer shorts and polos in rotation for a decent amount of time yet. For those of us who live in other, less forgiving locales though, cold weather is in sight, perhaps even by the start of next month. Fear not, though. In terms of versatility and possibilities, fall is perhaps the best season for menswear. The potential for layering sweaters with button-downs (and pairing those combinations up with slim pants and a crisp pair of shoes) should be exciting for those of us who live in colder climes, even with the possibility of freezing temperatures.

Namely, there’s one item that can take those of us in the cold through the fall and winter with relative ease and extreme versatility. They seem to be dwindling rather fast in stores as of now, but JCP’s Stafford Camlin wingtip boots could just be the snag of the season. Make no mistake, these are definitely a “wear anytime” boot, too, but it seems fall and winter is the particular sweet spot for boots.  This particular pair was picked up on significant clearance about three weeks ago, in the last size available at the local JCP, so beware.

The JCP Stafford wingtip boots in the flesh.

The JCP Stafford wingtip boots in the flesh.

JCP underwent a pretty extensive revamp through Nick Wooster a while ago, and have since been shifting slightly back toward the old ways, but with the upcoming fall line and these boots, they have some winners hanging around. As to the boots, they’ve already received high praise across the board, and the looks really can’t be beat. And for that price, too, you can experiment with their coloration a bit, as well.

For about $75 (or less depending on if you can snag a pair on the cheap before new stock comes in), you get a boot that works with jeans, chinos, cords, you name it. A boot with as solid a color of this also provides a nice bit of texture to an outfit, and something like this boot would go nicely with a  blue-on-blue combination. They’d work well with a darker-colored corduroy pant, as well. And even a crew-neck sweater and jeans tie in with these boots.  With fall, too, comes a richer palette of colors, like those burgundy pants as shown below.

Pants by CPO Provisions, from Urban Outfitters.

Pants by CPO Provisions, from Urban Outfitters.

Furthermore, they’re the perfect answer to the business-casual shoe that’s just different enough. It’s a boot, so it’s not a full-on dress shoe, but it’ll still provide loads of nice looks in the office (or perhaps trekking across campus) as the weather gets cold.

The boot style and perforations help set this shoe apart.

The boot style and perforations help set this shoe apart.

This particular pair has already seen a bit of break-in duty prior to fall, but there’s no question that they’ll be a staple through the fall and well into the winter. Since they’re not the priciest boots on the market, they can take a bit of a beating without too much worry, feasibly. And what’s more, they fit pretty comfortably. As Joe from Dappered notes in the above link, they do run quite large, so sizing down is critical. However, with that in mind, it makes perfect sense to hop on a pair of these boots while they’re still around.

And when cold weather does hit, you can reach for these boots time and again without worry about price tag or scuffs.