Style Suggestion: What to Wear for Cinco de Mayo

Editor’s note: For all manner of style suggestions covering everything from brunch to the holidays, head here.

As I sit here to write this post, it’s pretty wild that it’s already time to think about Cinco de Mayo — where has the time gone? And how are your 2016 style resolutions holding up so far? I’m still struggling to wear less blue, namely — the below outfit doesn’t necessarily move away from that color, either! With that being said, it’s important to recognize that Cinco de Mayo really does have historical significance — and yet, it’s a time a lot of us use to spend with friends at say, a patio bar crawl or the like. And if you’ve been cooped up inside all winter, it seems people need any excuse to get outside (heck, who doesn’t love a great brew regardless — am I right, or am I right?). At any rate, we’re combining style that’s part casual, part rugged and a little refined to combat warm breezes during the day, and possibly cool temps at night. Like what you see, or have other suggestions in mind? Give The Style Guide a shout over here. Onto the outfit!

The Jacket: JackThreads Trucker Jacket — $79

Unique design details and a classic indigo color make this the ideal piece of spring outerwear.

Unique design details and a classic indigo color make this the ideal piece of spring outerwear.

Just as we kicked off our suggestion covering what to wear to Sunday brunch with a JackThreads, so we begin this style suggestion with a tough trucker jacket that’s a positively stunning value — and it should come in handy if it gets breezy, too. The silhouette is a bit different than your standard denim jacket (note the covered placket and the front ridges on either side of it). Lest you think a denim jacket can’t work for you, note that it can be worn plenty of ways. It’s also worth noting that JackThreads’ creative director, Tony Kretten, was the man behind the relaunch of the GAP 1969 denim line — so he knows a thing or two about great denim.

The Shirt: Saturdays Surf NYC Esquina Denim Shirt in Light Washed Indigo — $115

The spring and summer answer to winter's dark denim shirt.

The spring and summer answer to winter’s dark denim shirt.

We’re going full-on denim on denim on the top half — but it’s no Canadian tuxedo. Lest you’re wary of pairing two shades of blue, note that this Saturdays Surf NYC oxford has nice texture and a color that’s significantly lighter than the jacket. It’s a simple, minimal shirt that could quickly turn into a workhorse spring styling piece — it would work well with slim tan chinos or even dark  blue jeans throughout the summer (don’t rule out a pair of tailored shorts, either). From personal experience, Saturdays Surf NYC shirts fit slim and hold up very well through repeated wear — a good thing considering the price tag.

The Pants: JackThreads Slim Chino in Stone — $49

A pair of pants to go along with the JackThreads jacket -- slim, stylish and affordable.

A pair of pants to go along with the JackThreads jacket — slim, stylish and affordable.

In this case, the darker blue jacket and lighter blue shirt are just fit for the cool tones of these JackThreads stone chinos. The brand crafts these with a slim fit and nice fabric, plus the price is (as always with JackThreads) exceptionally solid. Some slim khaki chinos would also work with the rest of this ensemble, as might some natural denim — and if you were lucky enough to pre-order the incredible Taylor Stitch Slim Chino in Stone, that’s a worthy pair of pants to keep in mind when matching up multiple shades of blue (although it doesn’t look like they’ll ship in time for this particular holiday).

The Sneakers: SeaVees Legend Sneaker Standard in Bleach — $78

Just as stylish now as it was decades ago.

Just as stylish now as it was decades ago.

SeaVees was among the first brands to really pioneer the classic plimsoll sneaker, and the silhouette has stood up to the years — the Legend Sneaker Standard is no different. These kicks are crisp, casual and timeless — they’ll pop nicely with the light grey chinos and the darker blue jacket, and the great thing about these kicks is that they’ll probably look even better a bit beat up. Plus, they’re comfortable and lightweight — perfect for hanging out on a patio as the sun sets. If those aren’t your speed, check out other stylish spring sneakers here.

The Belt: J. Crew Factory Braided Leather Belt — $18.50

A welcome and appropriate departure from a thin dress belt.

A welcome and appropriate departure from a thin dress belt.

Casual situations call for a change of pace from a slim, minimal dress belt — this is definitely one of those times. This J. Crew Factory braided leather belt works well in terms of adding some texture and visual interest to this outfit, and it works for spring (and summer, and fall … and winter). A striped webbing belt would also add a spring-friendly vibe to the look, yet the leather belt is going to be a bit more versatile across the seasons. If you happen to have the rugged vintage leather belt from this style suggestion, throw that on instead.

The Watch: AVI-8 Hawker Harrier II — $165

A sufficiently rugged watch ready for the rigors of a bar crawl.

A sufficiently rugged watch ready for the rigors of a bar crawl.

Are you familiar with AVI-8 Watches? The brand takes pride in producing authentic, tough and durable watches inspired by classic pilot timepieces. The story is an admirable one, and the product looks great — and backs it up with quality for a very solid price, too. The version of the Hawker Harrier II seen here is a bit less technically complicated than some of the other models from the same line (including this chronograph number), but it’s fitting for this particular occasion — it’s not too dressy, and it gives off a nice, rugged vibe. The combination of black and tan between the dial and the case is solid, and the 45mm diameter means it’s pretty beastly. If a smaller-sized watch might be more your thing, head to last week’s post on the best casual watches to buy now.

The Socks: American Trench Summer Footies — $13.50

An underrated finishing touch that could be crucial in keeping your white kicks pristine.

An underrated finishing touch that could be crucial in keeping your white kicks pristine.

Don’t underestimate the power of taking care of your feet this summer — and by extension, your shoes. A nice pair of no-show socks can help contain foot odor, make sneakers last longer and ultimately, prove much more comfortable for your feet. American Trench does standard fall and winter socks well, and they’ve even introduced some nice, spring-ready colors (in addition to the no-show socks you see here). Even if they’re only socks, the fact that they’re made in the USA at a family mill is another big bonus. They’ll definitely finish off this outfit the right way.

When approaching a situation like Cinco de Mayo, where you might be headed to a party to a bar and back, or multiple indoor or outdoor stops along the way, layering up appropriately is going to be key. The denim trucker jacket adds a rugged, bar-ready look to those modern, slim chinos — and classic white sneakers are a great piece of finishing footwear.   A tough, military-inspired watch serves a dual function — that of a neat conversation starter and a really solid watch. Plus, each of these pieces can work across the rest of the season in various outfits. That’s worth a toast in my book.

How are you dressing for Cinco de Mayo? Any pieces you would change or add?

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Florsheim

Style Suggestion: A Cozy Christmas

Editor’s note: For more Style Suggestions — including what to wear to that holiday party — swing through here.

Breaking news — Christmas is almost here! If you’re a big fan of the holidays, like me, and appreciate a festive atmosphere in the air and lights all around the cityscape (or your hometown), there’s really no better time to enjoy. But thankfully, the holiday also gives everyone a chance to rest, regroup and ideally, actually get home for some time off. Either way, Christmas and the events surrounding it don’t always have a set dress code — it could be a more casual evening of opening gifts with just the family, or a nice party with friends (hopefully, Ryan Gosling doesn’t drop by). So the style suggestion that follows definitely errs on the side of more casual, whether this is on Christmas Day itself or in the days leading up to. Bear in mind — this is just one suggestion to keep things from getting too sloppy, so mix-and-match (and buy) as you please! Note that we’ll cover a more dressed-up Christmas affair right here next week.

The Shirt: Tommy John Ringer Pocket Tee in Heather Grey — $34

This colorblocked pocket tee is a simple but effective upgrade from the pedestrian crewneck.

This colorblocked pocket tee is a simple but effective upgrade from the pedestrian crewneck.

So right off the bat, that price is a bit much more than most might pay for a T-shirt. BUT, bear with — Tommy John certainly seems to be the real deal as far as quality and comfort goes in the undershirt and T-shirt game. And its Ringer Pocket Tee (available in four colors) is soft, stylish and slim-fitting. Crucially, the color at the neck and pocket sets it apart just so slightly from a regular crewneck tee, even when that might be the cheaper option.  It’s these small style upgrades that can add a little thought to your look, and if comfort is part of the equation, it’s key to still look good. However, if wearing just a tee makes you wary, I’d reach for a great chambray shirt instead.

The Sweater: Old Navy Chunky Shawl-Collar Cardigan — $49.50 (When On-Sale)

A rich color and ribbed knit make this a solid house sweater for a cozy Christmas.

A rich color and ribbed knit make this a solid house sweater for a cozy Christmas.

Because it’s the heart of December, we’ll assume it could be a little bit chilly wherever you might be. That’s exactly the time to reach for a well-priced Old Navy cardigan. The burgundy color is a nice, on-trend nod to the season as a whole (although this cream JackThreads Shawl Cardigan could also be a neat, affordable pickup). But in this instance, the thick burgundy knit brings some nice contrast when paired alongside the lightweight T-shirt. As I’ve said time and again, a shawl-collar cardigan is a great, masculine style move that adds some rugged appeal to any outfit. Plus, who doesn’t love a cozy sweater? If it’s too warm out where you are, ditch it (if you’re lucky enough, that is!).

The Pants: JackThreads The Daily Jogger — $49.50 OR Classic Dark Denim

A dark color and trim cut help these wear less like sweats and more like jeans. Yes, you got that right.

A dark color and trim cut help these wear less like sweats and more like jeans. Yes, you got that right.

As we talked about above, Christmas can go one of two ways — more casual, or dressier. In this case, if you’ve got the option to go more laidback yet want to avoid wearing pajama pants, we’re going out on a limb to recommend a pair of tailored sweatpants in a dark color. JackThreads continues to get a lot of things right with its new menswear line, and stylish essentials at low prices like these are why. Again, if sweatpants still feel too casual, a solid pair of dark denim never fails (I’d recommend Mott & Bow, who makes slim jeans like its Hester model with a comfy hint of stretch). If sweats are too hot, reach for their laidback but just as comfy alternative — the well-crafted sweatshort (like these from my friends at Pistol Lake).

The Sneakers: GREATS Brand Royale Chukka — $152 (On-Sale)

Camel plus black in a chukka silhouette = dressier sneakers than the norm.

Camel plus black in a chukka silhouette = dressier sneakers than the norm.

If sneakers seem a silly option for the middle of winter (and they very well might be if there’s a ton of snow), I’d urge you to go with a reliable (but cheaper) desert boot instead. If, however, you’re able to rock some chukka sneakers from GREATS, you’ve found a style choice that fits right in with fall & winter yet feels more comfortable than a thicker boot (note that Reef’s Outhaul Lux Chukka does that, too). The Royale Chukka definitely checks all those boxes, and even more crucially, the camel color plus black sole is a combo that feels a little dressier than a plain pair of captoe sneakers. These sneakers can be worn through the rest of winter in the right weather, and into spring with some lightwash jeans, too — that’s the gift that keeps on giving.

The Watch: Timex Weekender 40mm — $46

A black leather strap and that simple Timex dial create the ideal happy medium for the rest of this outfit.

A black leather strap and that simple Timex dial create the ideal happy medium for the rest of this outfit.

Just as in this site’s Thanksgiving Style Suggestion, a Timex is the affordable watch pick once again. In this instance, Timex’s classic weekender dial keeps the watch more casual, but the black face and slip-thru black leather strap makes it ever so slightly put-together. Yet, it’ll still look right at home with this outfit in terms of color and styling potential — it’s just that simple and versatile. Lest we forget, this watch can be mixed and matched with other NATO straps — that’s like getting a new watch for about $10.

The Socks: Richer Poorer Herald Socks — $12

A small way to pump some pattern into an outfit -- for a low price.

A small way to pump some pattern into an outfit — for a low price.

Whereas the rest of this outfit mainly sticks to solid basics, these socks inject some life into the ensemble in a fun way. And assuming you’ll be kicking around without shoes on for a bit, clean, hole-free socks are a must (truly). Throw in a fun polka-dot pattern in a color that complements the rest of the outfit, and you’re set. The oatmeal color of these socks is also just different enough if you go with a heather-grey T-shirt (or even a blue chambray), and the navy dots complement the cardigan and the sneakers, too. Plus, Richer Poorer socks are springy and breathable — not a  heavy wool set.

While the above outfit might not work for everyone, here’s hoping you do get the chance to kick back in a more casual fashion this Christmas — and when that time comes, I hope you’ll keep some of these picks in mind (because who doesn’t love looking their best all the time?). Think I missed anything? Let me know your picks for the holiday season below!

Ben Sherman US