Dress to Impress.
Young men are in a bit of a predicament right now. While most of their wardrobe comprises streetwear looks tailored to popular sneaker silhouettes from a few years ago, there’s been a shift to dressing more like the father figure they’ve always looked up to. Vintage watches, and the watch games as a whole have been a signifier for young men to begin dressing smarter. Whether it’s button-down dress shirts, tasseled loafers, or suit trousers… the hype is real.
However, it’s hard to dismiss the fact that a lot of young men have closets chock full of streetwear-oriented outfits, as that’s what we grew up with. This guide will break down four different variants of smart shoes, detailing how to style each and every one with the streetwear that you already own.
THE LOAFER
While the origin story of the loafer is contested, the functionality of the shoe remains the same. Loafers were developed to be casual or work footwear, utilised as a secondary shoe in a rotation full of dress shoes like derbys, oxfords, and monk straps. Today, the shoe is reoriented as a step up, deviating from sneakers and other casual shoes which have more recently risen in popularity.
The quick and easy way to style a loafer is quite simplistic. For instance, baggy pants favour a loafer as they have the ability to sit right at the forefoot, exposing the shoes’ detailed toe box and suiting wide-to-narrow proportions very well. Not all loafers are designed with more than just a simple strap on the toe, but the pairs that you will see across social media tend to. Dr. Martens’ Adrian Tassel loafers feature an added lip of leather, with two tassels dangling down onto the toe box. Duke and Dexter swing the complete other way, including off-colour toes with painted graphics on them.
Baggy jeans offer a bit of internal solidarity, as it’s easy to get away with a thick pair of wool socks or something protective as they will rarely be exposed. Loafers aren’t fun to break in, so wearing a thicker sock will ensure comfortability as you go through that process.
The Weekday Astro or Galaxy has a chokehold on ‘Fashion Tok’ right now due to the relatively affordable price point and outright bang for your buck. They’re soft and flowy, sitting just at the forefoot on most loafers. If you’re rolling in it a bit more, the Acne Studios Super Baggy Fit jeans are a terrific investment piece that have the potential to live out the smart shoe trend.
Those two pairs of denim could be paired with the two loafers mentioned above, along with a vintage gem. Dr. Martens’ Adrian Tassel loafers have a classic silhouette and barbershop quartet aesthetic due to the tassels. However, the arch on the sole is unique, so ensure you try these on in-store before buying. Duke and Dexter create loafers for the artsy boy, pairing their staple penny loafers with giddy graphics like intertwined snakes and lipstick-stained kisses. The perennial G.O.A.T. of loafers is the G.H. Bass Weejun Penny loafers. These are made to stand the test of time and can be found quite easily on second-hand websites, previously broken in and vintage-tinged to your liking.
Photo credit (left to right): Duke and Dexter, Dr.Martens, G.H. Bass
THE OUTRIGHT DRESS SHOE
The last time you wore an outright dress shoe was probably prom or a wedding, and odds are you bought them to withstand the evening’s festivities from a retailer at a discount. However, as leather jackets and button-downs become prominent, this gives you the easy opportunity to throw on a pair of slacks, or a vintage leather jacket, and smarten up your look with a pair of dress shoes.
Slacks, or suit trousers, were designed to sit at the ball of your ankle, letting the shoe do all of the talking. A good pair of suit trousers don’t draw attention to themselves, rather they act as a seamless blend from statement jacket to dress shoe. Fast-fashion brands do a surprisingly good suit trouser, but the best option out there are the Uniqlo Pleated trousers. These feel like a pair of sweatpants, appear to be of a thicker wool during the eye test, and will suit a more elevated outfit decision of dress shoes and leather jacket. This outfit can be kept more street-oriented by wearing a boxy and cropped t-shirt beneath the jacket.
Terrific options for outright dress shoes include brogues, which are laced-up dress shoes with perforated designs along the toe and throughout the midfoot. Thom Browne makes a brilliant brogue, as well as Churchs and Russel & Bromley. Derbys are another silhouette to checkout. Being originally popularised as the Dr. Marten 1461, this silhouette fits those who prefer a wider slack, suiting a more enlarged jacket on top.
Photo credit (left to right): Dr. Martens, Church’s, Thom Browne
THE BOOT
When I think boot, my mind instantly goes to one of two things. We’re either talking biker gang, chunky silver rings, smooth leather gilet, cut-off tank top, and thick leather moto boots, or menswear YouTube aficionado from 2016, pairing skintight trousers with leather or suede Chelsea boots. If you don’t identify with either of those stereotypes, then fear not.
The key to a good boot is craftsmanship. It’s easy to find a pair of fast-fashion Chelseas or chukkas and wear them for a season until they crumble. But, like Japanese selvedge denim, a solid pair of boots will mould to your foot and aesthetic, lasting you a decade. Both of the aforementioned silhouettes suit denim, as their ability to be stacked is one of their selling points. Chelseas often have a narrow toe, making that wide-to-slim proportion look quite nice below a cropped jacket of some sort. Bombers and denim jackets will be a go-to this spring, giving you the chance to rep your newly purchased mainstays.
Timberland 6” boots are an easy choice right now as it seems like every TikTok influencer has worn their pair with the tongue exposed under a pair of baggy denim. But, Chukka boots from Clarks or Grant Stone work best underneath a slimmer fitting pair of jeans, preferably with a two-finger width cuff at the base. Chelsea boots can receive the same treatment, with Reiss and Prada making some showstoppers.
Photo credit (left to right): Clark’s, Reiss, Prada
THE MULE
Oh the mule, the perfect transitional shoe. That is, from grocery store groutfit to neatly put-together streetwear. Like the Chelsea boot, these come in lots of different materials, although suede and leather seem to be the most prevalent. They offer a rounded toebox, exposed heel and tend to be lined or re-inforced with a comfortable insole. Mules can act as the utility shoe in your collection, serving the purpose of being the last thing you think about in your outfit.
These work best beneath any baggy pant, whether they’re cargos, denim, khaki’s or suit trousers. Some of the most inclusive outfits that let the mule stand out are with a hoodie, which is cropped or has been folded in for a cuffed look, with a pair of baggy jeans or cargos. This outfit gives a put-together look all while being incredibly cozy.
Birkenstock Bostons have been the talk of the town for years now and still remain one of the best options for those transitioning into more smart shoes, however, leather iterations will do a better job of achieving the elevated look. Viron is a vegan company that makes sustainable mules that are just as comfortable as they are stylish, with the toebox offering a similar look to a loafer whilst extending to about the achilles, letting you get away with the loafer look without the heel pain. Suicoke offers a more athletic-looking mule due to its full rubber build, and for the dressier, alternative types, take a look at Toga Pulla for leather mules with hardware. For a more interesting take, Marni offers monster feet-looking mules with mohair fuzz, as well as multi-colour woven uppers for a bit of a hippy look.
Photo credit (left to right): Viron, Toga Pulla, Marni
