Casualwear can sometimes feel messy. Without the guidelines in traditional tailored clothing, many guys feel it’s hard to understand how to dress casually, but well. The rules are always changing; there are too many options. While everyone can look good in a dark suit, white shirt, and dark tie, there’s no universally “good” uniform once you step into more casual attire.

In some ways, however, the two worlds aren’t that different at all. There’s no inherent logic to tailored clothing. The rules for classic men’s dress come out of socially embedded norms, which people once knew intuitively. Worsted suits were for the city, tweed sport coats for sport, which is why oxfords look better with the first and derbies with the second. Today, those “rules” have been made explicit, but to really understand how to wear a suit-and-tie, you have to develop a sense of when something looks “right.”

Casualwear doesn’t have the same rules, but it’s governed by the same principles. Years ago, my friend David wrote about the irrevocable power of some art dealers to discern “quality from trash, real from fake, inspired from derivative.” Such dealers call this The Eye, which is their way of saying how they can tell when something looks “right.” As David writes: “attention and exposure to a wide variety of interesting objects is what sharpens The Eye.” At the end of the day, whether you’re in jeans or a sport coat, it comes down to developing that sensibility through exposure. Knowing the general scope for an aesthetic gives you an idea for where you can start building a wardrobe — and where you can take it. By understanding the visual language, you’ll know how to play within a style’s boundaries and how to push its borders, and thus get why some combinations work and others don’t.

Last week, we covered some of the more basic and popular casualwear styles, including Americana, prep, and workwear. Today, we’ll look at more forward facing aesthetics. And again, we’ll list some things that may be useful for each niche, as well as links to relevant sites for further exploration. Find a style that speaks to you and delve in.

Reworked Classic Casualwear

Reworked Classic can seem redundant to last week’s Basic Casualwear and Rugged Workwear, but we think it’s distinct. The problem with Basic Casualwear is that it can feel a bit vanilla today, sometimes bordering on business casual. As such, the style can sometimes lack personality. Workwear, on the other hand, can feel anachronistic and overly rugged, maybe at odds with some people’s personalities. There are ways to safely modernize that look, but doing so can, at times, land you back in generic territory.

Reworked Classic is our term for a more contemporary and expressive take on classic casualwear. It draws from Americana, prep, and workwear, but has its own spin. Often times, the clothes come from Japan, where designers heavily borrow on vintage Americana, but remix it with a designer sensibility. Jackets and shirts have oddly placed pockets; trousers have either been slimmed up or made very full. The clothes have a sense of humor about them — they’re playful, offbeat, and distinctively modern.

Like with all of the styles in today’s post, there aren’t any “essentials” to speak of, but many of us here at Put This On wear Reworked Classic Casualwear when we’re not in suits and sport coats (that includes Jesse, Pete, and me). Some things we find useful:

Tops: Oxford-cloth button-downs in solid white and light blue; chambray shirts in light blue; plaid flannels in staple colors such as navy, burgundy, and green; vacation style shirts in a variety of prints, often two-tone in color.

Oxford-cloth button-downs in solid white and light blue; chambray shirts in light blue; plaid flannels in staple colors such as navy, burgundy, and green; vacation style shirts in a variety of prints, often two-tone in color. Pants: Slim-straight raw denim jeans in indigo; workwear style chinos in slim and relaxed cuts; Ghurka closure shorts in tan; olive colored fatigues

Slim-straight raw denim jeans in indigo; workwear style chinos in slim and relaxed cuts; Ghurka closure shorts in tan; olive colored fatigues Knitwear: Chunky shawl collar cardigans; textured fisherman- and Norwegian-style sweaters in navy and grey; Shaker style sweaters; plain Shetland sweaters; stout cotton crewneck sweatshirts in marled grey.

Chunky shawl collar cardigans; textured fisherman- and Norwegian-style sweaters in navy and grey; Shaker style sweaters; plain Shetland sweaters; stout cotton crewneck sweatshirts in marled grey. Outerwear: Navy Nigel Cabourn Hospital jacket; tan Kaptain Sunshine photographer jacket; navy Kaptain Sunshine Traveler coat; various military-styled field jackets in olive; Kapital Ring coat in olive; Engineered Garments Bedford jacket in navy moleskin and beige corduroy; Ten C liner; vintage Patagonia deep-pile Retro-X fleece in cream; Nigel Cabourn Canadian military bomber jacket in olive; RRL Morrow leather jacket in brown; French chore coats; Camoshita Balmacaan coat; MHL mac raincoat in navy; Engineered Garments utility vest in olive; Engineered Garments deck jacket in olive; and various vintage safari-style jackets

Navy Nigel Cabourn Hospital jacket; tan Kaptain Sunshine photographer jacket; navy Kaptain Sunshine Traveler coat; various military-styled field jackets in olive; Kapital Ring coat in olive; Engineered Garments Bedford jacket in navy moleskin and beige corduroy; Ten C liner; vintage Patagonia deep-pile Retro-X fleece in cream; Nigel Cabourn Canadian military bomber jacket in olive; RRL Morrow leather jacket in brown; French chore coats; Camoshita Balmacaan coat; MHL mac raincoat in navy; Engineered Garments utility vest in olive; Engineered Garments deck jacket in olive; and various vintage safari-style jackets Shoes: Kapital naval side-zip boots; vintage Ralph Lauren Country cookie boots; Alden boots in dark brown calfskin and shell cordovan; Viberg service boots; Pretziada shepherd boot in black; Engineered Garments x Vans slip-ons in off-white; LL Bean duck boots; and Russell Double Moccasin Bottom Birdshooter boots

Like with workwear, there’s a traditional sense of masculinity here that makes the style easy for many guys to wear. It’s geographically neutral and works well for many lifestyles. The clothes have that better-with-age quality we love. And the baseline for many of the combinations will feel intuitive. Flannel shirts go with jeans; oxford-cloth shirts with chinos. They may or may not have interesting details or silhouettes, but once you throw on a coat from this category, you instantly have a more stylish ensemble. At the same time, the clothes are distinctively modern enough to not feel like repro-wear. You’ll never look like an early 20th century train engineer in these clothes — just someone who loosely takes inspiration from that era.

The downside is that the stuff is generally expensive. You can get around this by supplementing with vintage; checking second-hand markets such as eBay, Grailed, and Marrkt (the last of which specializes in this look); and picking up the basic pieces from more affordable brands. I love chambray shirts from Chimala, but they’re $300. The ones from J. Crew’s Wallace & Barnes, however, can be had for as little as $50 on sale. And while we really like 3sixteens’ SL-100x jeans and Levi’s Vintage Clothing’s 1947 501s, you can also get great jeans from Gustin for about $70. This will leave you with a bit more money for outerwear and footwear, which are how you really bring this look into its own.

Some of our favorite brands here include Engineered Garments, Nigel Cabourn, Kaptain Sunshine, RRL, Levi’s Vintage Clothing, and Kapital. Stores such as No Man Walks Alone, Unionmade, The Bureau Belfast, Blue in Green, and Canoe Club are also worth a closer look. See this post for more ideas on how to build this sort of wardrobe.

Brands and Stores: Unionmade, The Bureau Belfast, Frans Boone, Kafka, Cultizm, Marrkt, Reliquary, Stag Provisions, End, Mr. Porter, SSENSE, Private White VC, No Man Walks Alone, Standard & Strange, Pancho & Lefty, Blue Button Shop, Blue in Green, Alpha Shadows, Haven, Superdenim, The Garbstore, Independence, Indigo & Cotton, Jack Straw, Context Clothing, 14oz, Francis May, Magasin, Mohawk General Store, Nifty Do, Oi Polloi, Aphrodite, Snake Oil Provisions, Supply & Advise, Milworks, Division Road, Unmarked, SEH Kelly, Battenwear, Nepenthes, Yuketen, BlackBlue, Monitaly, Nigel Cabourn, Snow Peak, Miloh Shop, Canoe Club, Cotton Sheep, and Trading Post

Blogs and Forums: Die, Workwear, Guillotine, GQ Style, Well Spent, Blamo, Styleforum, and Reddit Male Fashion Advice

Refined Casualwear

It’s difficult to navigate through the narrow space between tailored clothing and casualwear. There are a lot of guys today who love the look of tailored clothing and try to transpose some of those sensibilities into more informal attire (The Rake recently asked, “is it possible to look sophisticated while wearing swimming trunks?”). It can also be something of a high wire act trying to create a more classically grounded outfit without spilling over into the Basic Casualwear territory described last week. You can find a ton of casualwear at shops such as Hackett, Loro Piana, and Brooks Brothers, but a lot of it isn’t going to look that different from the things sold at J. Crew (even if they’re made from better materials).

It’s possible to do a more refined version of casualwear, but you have to really lean into the casual side of things. Let go of traditional ideas in classic men’s dress. While it’s possible to mix your highs and lows — such as throwing a waxed cotton Barbour over a flannel suit — most guys are better off dressing coherently. Refrain from wearing neckties with casual jackets; don’t pair things such as sockless wingtips with shorts. And let go of traditional notions of how clothes should fit. Jeans shouldn’t drape like trousers (they can’t anyway, as denim is too stiff). Outerwear doesn’t need look perfectly tailored (it’s often better when it’s relaxed and slouchy, giving the wearer a more comfortable and natural look). If you’re going to go casual, go casual. Companies such a Trunk Club, Stoffa, and S.E.H. Kelly do an exceptionally good job in this category (the first image at the top of this post is from S.E.H. Kelly).

For fall and winter, this can be as simple as a waxed Barbour with a Shetland sweater, some jeans, and heavy boots. Or it can be a pair of wool trousers with a loosely cut topcoat, the second of which will give you the general appearance of tailored clothing without actually looking like businesswear. Manolo editor Andreas Weinas can be seen above wearing this sort of outfit with a chunky turtleneck sweater, which dresses things down further (he actually has a sport coat under there, but … ignore that part). Corduroy trousers, moleskins, rumply chinos, and jeans are all good alternatives to flannel trousers. And instead of pairing sleeker oxfords or derbies with these sorts of looks, again lean more into the casual side of things. Chunkier, rounder toe boots can often look more stylish in these contexts.

Spring and summer are trickier, but you can do the same with jeans and safari jackets, or chinos with citified bombers, such as a Valstarino. Again, just avoid trying to look too tailored. Safari and field jackets often benefit from having a bit of slouchiness. When the shoulder seams fall perfectly on the shoulder bone, and the body is too perfect, the jacket can look too much like a shirt, losing all of its charm and casual sensibility. Even Bruce Boyer, one of the best dressed classic menswear guys around, can be seen above in a pair of washed jeans and loosely cut navy jacket (plus a bucket hat!). Casual clothes needn’t fit so perfectly — they often look better when they don’t.

Some things I find useful:

Tops: Oxford-cloth button-downs; slightly dressier versions of chambray or denim shirts; loosely cut popover shirts in solid white and light blue; linen shirts in solid white and light blue

Oxford-cloth button-downs; slightly dressier versions of chambray or denim shirts; loosely cut popover shirts in solid white and light blue; linen shirts in solid white and light blue Pants: Slim-straight raw denim jeans in indigo; corduroy trousers in dark brown; tan chinos with a slightly higher rise; grey wool trousers in various weaves; moleskin trousers in mid-brown

Slim-straight raw denim jeans in indigo; corduroy trousers in dark brown; tan chinos with a slightly higher rise; grey wool trousers in various weaves; moleskin trousers in mid-brown Knitwear: Plain Shetland sweaters in navy, brown and grey; linen sweaters from Inis Meain (they have more of a springback quality to them, making them a bit like wool, but are more breathable); Scottish cashmere cable knit sweaters in bottle green, navy, and grey; cream colored Aran sweaters; grey cotton crewneck sweatshirt in marled grey

Plain Shetland sweaters in navy, brown and grey; linen sweaters from Inis Meain (they have more of a springback quality to them, making them a bit like wool, but are more breathable); Scottish cashmere cable knit sweaters in bottle green, navy, and grey; cream colored Aran sweaters; grey cotton crewneck sweatshirt in marled grey Outerwear: Barbour Bedale in green; Holland & Holland safari jacket in tan; Stoffa flight jacket in brown suede; Valstarinos in brown leathers; Eidos topcoat in grey herringbone tweed; Kaptain Sunshine Traveler coat in navy Melton wool; Belstaff Roadmaster; Enrico Mandelli leather bomber jackets; Aspesi military-style field jackets in olive green

Barbour Bedale in green; Holland & Holland safari jacket in tan; Stoffa flight jacket in brown suede; Valstarinos in brown leathers; Eidos topcoat in grey herringbone tweed; Kaptain Sunshine Traveler coat in navy Melton wool; Belstaff Roadmaster; Enrico Mandelli leather bomber jackets; Aspesi military-style field jackets in olive green Shoes: RM Williams Craftsman boots in brown; Crockett & Jones Breacon chukka in brown pebble grain leather; JM Weston 180 penny loafer in brown; Superga 1705 in classic white; LL Bean duck boots; Alden penny loafers in suede; Alden unlined chukkas in suede

Brands and Stores: The Armoury, Trunk Clothiers, Private White VC, No Man Walks Alone, Stoffa, Timothy Everest, Cavour, Drake’s, Sunspel, Ledbury, Proper Cloth, LL Bean, O’Connell’s, Doherty Evans & Stott, Christian Kimber, Beige Habilleur, Ben Silver, Borghini, Anglo Italian, Braun Hamburg, J. Press, John Simons, John Smedley, Berg & Berg, Cordings, Ralph Lauren, Brooks Brothers, Stoffa, Emmett London, Loro Piana, Guideboat Company, Malford of London, Marcus Malmborg, Paul Smith, Paul Stuart, Quality Shop, S.E.H. Kelly, and Sid Mashburn

Blogs and Forums: Permanent Style, Timeless Man, The Rake, The Grey Fox, Jackal Magazine, Styleforum, Reddit Male Fashion Advice, and Manolo

Contemporary Casualwear

Finally, we have Contemporary Casualwear, which is admittedly an ill-defined category. This can include everything from techwear to streetwear to dark, art povera looks. Some are easier to wear than others, while some may require you to fully jump in. Rick Owens, for example, can look fantastic if you fully embrace the style, but be lackluster if you try to wear it in more conservative ways (sorry Jack).

We’re using the term Contemporary Casualwear here, however, to underscore the porousness of some of these styles — the ease with which you can combine things in any number of ways, including integrating them into more classic wardrobes for a modern look. And doing so can give you some versatility in a wardrobe, allowing you to create outfits that look more at-home in certain settings than strictly heritage-inspired ensembles.

For example, I often wear an oversized bomber jacket from Robert Geller with my Buzz Rickson sweatshirt and 3sixteen jeans; or pair a grey, hooded Stephen Schneider “Merino” coat with Eidos’ Shaker-style knits and grey wool trousers. My most frequently worn piece of outerwear is also a black leather jacket from Maison Margiela (pictured in the first photo above). That goes with everything from tailored trousers to raw denim, casual button-ups to white tees.

One of the nice things about Contemporary Casualwear is that you can be a bit more experimental in terms of patterns and silhouettes. Think of long, flowing topcoats thrown over textured sweaters, which have dropped shoulder seams and wider necklines. T-shirts with boxy bodies and slightly lowered chest pockets; trousers with a relaxed fit and higher rise; camp-collared shirts with unusual patterns. Depending on the pieces in your wardrobe, you can combine things in one way and get a contemporary look. Wear it another way to make it Refined Casualwear or Rugged Workwear.

Given the size of this space, it’s even harder than previous categories to recommend useful basics. A lot depends on the specific iterations you’re interested in exploring — a slightly more streetwear inspired look by combining a pair of Nikes with a French chore coat, or the kind of minimalistic, but expressive styles seen at E. Tautz and Lemaire (who often mix ’90s-era Helmut Lang with ’80s-era Armani). Some of my favorite designers in this space include Lemaire, Stephen Schneider, Evan Kinori, Our Legacy, and Maison Margiela. I also really like stores such as No Man Walks Alone, Neighbour, Totokaelo, Namu Shop, Maas & Stacks, Mohawk General Store, Magasin, and Mr. Porter. But they’re hardly the only ones worth checking out. Dig around in the links below to see if any stores or brands inspire you.

If you’re thinking about just dipping your toes into this space, however, a long and loosely cut topcoat, textured sweater in navy or grey, and slim cut jeans or chinos can be a solid springboard for getting into other niches. Feel free to be a bit more experimental and take inspiration from both the men’s and women’s side of the media aisle. Often times, some of the most interesting things here either come in from womenswear collections, but are adapted for men, or the two happen concurrently (I’ve listed some of my favorite capital-F fashion sites below). StyleForum and GQ Style are also worth following.

Brands and Stores: Namu Shop, No Man Walks Alone, Maas & Stacks, Notre Shop, Oak NYC, Neighbour, Need Supply, The Ensign, Up There Store, Slamjam Socialism, Other Shop, Bodega, Totokaelo, Haven, Mohawk General Store, Roden Gray, Matches, Martin Margiela, Lemaire, Deveaux, Le Rayon Frais, E. Tautz, East Dane, Mr. Porter, End, Far Fetch, Goodhood Store, Stephen Schneider, Dover Street Market, Second Layer, Nike Lab, Acronym, The Loit, LN-CC, Tres Bien, Magasin, Acrimony, APC, Margaret Howell, Our Legacy, Harmony, De Bonne Facture, American Rag, Oi Polloi, Oki Ni, Nitty Gritty, SSENSE, Wrong Weather, CHCM Shop, Robert Geller, and Suspension Point

Blogs and Forums: ShowStudio, Dapper Kid, Dazed, Grailed Dry Clean Only, GQ Style, Highsnobiety, Garage, Racked, The Cut, The Rosenrot, Style Bubble, Man Repeller, Vogue Runway, NYT Fashion, Wall Street Journal, Scandinavian Man, Styleforum, Fashionista, The Sartorialist, Hypebeast, Blamo, Falling Upwards, Esquire, Third Looks, and Reddit Male Fashion