Your Most Common Menswear Questions, Answered

A little while back, we sent out a missive soliciting reader questions on the world of style. You lot did not disappoint — all manner of vestiary concerns hit our inbox, from dressing for a Zoom interview (yes, put on pants even though they’re not visible) to wedding-guest style etiquette (it ain’t about you, tone it down).

We noticed, however, that there were also certain questions that came up again and again, and thus we thought we’d put together this handy primer in partnership with our friends at Neiman Marcus to tackle the most common style queries many fellas seem to have.

We enlisted the assistance of Bruce Pask, Men’s Fashion Director at both Neiman Marcus and Bergdorf Goodman, and he and your correspondent got to answering. Bruce is one of the most stylish cats out there and I’ve been spending more money on clothes than is reasonable for most of my adult life, so you’re in capable hands.

Read on and dress well.

“How do I wear sneakers with a suit?“

Bruce Pask: I think it is very important to consider the character of the suit and underpinnings. Trim, more sleek and modern-style suits are more conducive to a sneaker pairing than more traditional, sartorial, dressy “business” suits. A slimmer lapelled single-breasted suit with a flat-front pant is a great candidate for sneakers, and make sure to keep pant length just hitting the collar of the sneaker, with only the slightest break in the crease. Plain hem, not a cuff. Conversely, a dressier style of suit — say a peak lapelled or double-breasted suit with pleated trousers — would be better matched with a pair of dress shoes. The other important consideration to take into account is what you are wearing underneath the suit. Sneakers are more appropriate for casual underpinnings like a shirt with the top button undone or a fine gauge knit crewneck or polo shirt. A shirt worn with a necktie will probably be better paired with a dress shoe or loafer.

“How can I pull off denim on denim?”

Danny Agnew: The Canadian Tuxedo Conundrum comes up again and again in these types of Q&As, and I fall firmly in the camp of “yes, do it, it’s cool.” I certainly wouldn’t be the first to suggest that the key is making sure the denim pieces differ in hue and then invoke Jay Leno as a cautionary tale, but it does bear repeating. I’d also say that lighter shirt/darker jeans looks better, and the more weathered and beat-up the shirt, the better. A pair of suede boots tends to round out the proceedings nicely, and you should feel free to beat the hell out of those as well. The goal here is simple and rugged.

“Can I wear a blazer with shorts?“

BP: Questions like this always hinge on the wearer’s self confidence and willingness to make a bit of a bolder statement. I say absolutely yes, you can wear shorts with a blazer or sportjacket when it is seasonally and occasion appropriate. Seersucker, madras and linen jackets are perfect candidates for pairing with shorts. When we are traveling and socializing again, a summer party, a weekend evening out on the town, or a stay away at a resort are all occasions that would be a great choice for shorts with a jacket. If attending a party, I would make sure to double-check any wardrobe guidelines …you don’t want to be the only one in the room with bare legs. Or maybe you do! That’s fine too. 

“Is it ever ok to wear a dress shirt untucked?”

DA: To me, this question speaks to the general misunderstanding of what a “dress shirt” actually is — I know a lot of guys who use the term as a catchall for any shirt with a collar and buttons down the front, but in reality an actual dress shirt is one that is cut longer and (typically) features no buttons on the collar. I would personally never wear one of these untucked just because it’s meant to be worn with a suit, and while I’m all for freedom of sartorial expression, I do believe that anyone who wears a suit with their shirt untucked deserves to be thrown in the stocks. Now a sport shirt, on the other hand, is a different story. Cut shorter and with a more casual bent (and, it bears noting, usually featuring a button-down collar), this type of button-up looks great untucked, from plain oxford versions (either white or otherwise) to plaids and other patterns.

“Can I wear white after Labor Day?“

BP: I think the most important factor to consider here is the weather and where you are geographically. In areas with tropical or warm climates almost year around — say Florida, Arizona, Southern California, etc. — I think you can most likely wear white (and lightweight linen fabrications of any color, really) at any time. Up north, say NYC or Boston, where the weather fluctuates much more, I would follow a bit more closely to the guideline that white is traditionally worn between Memorial Day and Labor Day. But there is flexibility. Basically, when it’s warm and sunny out, white is most likely an appropriate color to wear wherever you are. White denim jeans are an exception and wearable year around wherever you are in my opinion, depending upon your comfort level and preference. Nothing chic-er than a camel coat, grey turtleneck sweater, and a pair of white jeans for walking around the city in the fall. 

“How long should my suit jacket be?”

DA: A general rule of thumb is that when you stand with your arms at your sides and make a fist, the punchin’ part of the fist should be roughly even with the hem of your jacket. A little shorter = more fashion forward, a little longer = more formal/business-y. With that out of the way, I’d like to focus on how loud your jacket should be, and the answer there is “louder than you think.” Not enough guys know the swaggy feeling that comes with putting on a suit or blazer in a left-of-center color or pattern, and I will keep banging the drum for it as long as I have to. Guaranteed compliment-getter, every time.

“Can I wear a T-shirt under a suit?“

BP: The answer is yes, but as in the above question about sneakers with a suit, take into account the character of the suit you are wearing and where you are wearing it. A T-shirt is best worn with a more sleek, slender, modern suit, most likely with notch lapels and flat-front pants. For more casual, work-appropriate occasions I would make sure the tee is logo-free and not a white undershirt from a multi-pack. Darker colors, navy, light and charcoal grey, and black feel a bit dressier and most appropriate. Cotton or cotton/silk tees are good, and finer-gauge, merino-wool, lightweight knit crewneck sweaters dress the look up even more. If you want to wear your suit with a tee for a night on the town, whether to a club, a performance or dinner, feel free to share your message or concert tee as you prefer. 

“How should I layer my clothes?”

DA: Rather than tell you how to layer your clothes (which would take forever, being that it’s entirely season-dependent and also open to a great degree of personal interpretation), I thought it might just be good to spotlight a couple of my favorite layering pieces for spring. I’ve been a big fan of the short-sleeve henley for a long time, just because it looks cool and kinda macho on its own and then the buttons make for something a little more interesting at the neckline when you throw something over it. A lightweight bomber jacket as about as idiot-proof as it gets, insanely versatile and looks good on pretty much everyone. A traditional cardigan is also a big versatility win for spring/summer, as it really plays with shorts (over a shirt, please don’t wear just a cardigan and shorts) and also adds some welcome personality under just about any jacket.

“How far should my pocket square stick out?“

BP: A pocket square is considered an accessory, so it shouldn’t dominate your jacket, but there isn’t a set measurement. There are numerous ways to fold a cotton or linen pocket square, completely subject to personal preference. I tend to go with a skewed, slightly asymmetrical version of that classic ’60s straight-across fold. I fold the square in half, then in half again, and then in thirds so the width just fits into the pocket, then with the edges up and out I just give the rear third a bit of a tug so it emerges just slightly from behind the front so the square is not perfectly straight across, with maybe 1/2-an-inch peeking out from the chest pocket. Brunello Cucinelli is the master, if not the originator, of this method, and his styling looks great. A nice detail; thoughtful but not overwhelming. For silk pocket squares and dressier occasions, I prefer the “puff and point” method: pinch the pocket square at the absolute center then bring the four corners — “the points” — together behind the pinch or “puff”. Insert into pocket, with the puff in front of the points and tuck in until just a bit is showing at the top, maybe 1/2 to 3/4 of an inch, depending upon your preference. Finally, the “pouf” is the dressiest method and requires a little bit of artful fussing, but it’s easy. Grab square from the center again, the “pouf”, and simply tuck it into the pocket with only the pouf exposed at top, with the corners hidden inside the pocket. Then fuss with it a little bit so it has a little bit of and abstract floral or “rosy” look, but still only about 3/4 of an inch to an inch protruding from the pocket. 

“Are pleats on pants cool again?”

DA: I might argue that they’ve always been cool depending on your stylistic leanings, but I take your point — ‘twas indeed a time when the pleat conjured images of uncool dads and middle management. They’ve been enjoying a fashionable resurgence of late, however, in a variety of different styles. A “light pleat” (like the Gucci pair below) is a great way to dip your toes into pleated waters, but for my money I’d say swing for the fences with something more in-your-face and really lean into the throwback vibes. Drawstring numbers have also been popping up all over the place and are a great sporty alternative that look really cool paired with a tee and sneakers.

“Should guys wear jewelry?”

DA: It’s 2020, y’all — any sort of gendered notions regarding jewelry (or even just clothing in general) gotta go. Throw a diamond brooch on your blazer if you’re feeling saucy, I say. That being said, for jewelry novices feeling a little trepidatious, there are a few easy entrance points. A leather rope bracelet with a dash of metal hardware is a nice bit of understated wrist adornment, and IMO looks pretty cool layered with your favorite watch. Gold chain necklaces have been enjoying a moment, seen on the necks of stylish cats like The Rock, Donald Glover and hearthrob-of-the-moment Paul Mescal of Normal People (whose character’s thin gold chain has its own Instagram account). Rings are a slightly trickier proposition (ain’t no one trying to be Johnny Depp), but nobody ever went wrong with a single gold signet, even in addition to a wedding ring.

Hero image courtesy of Alexey Strelkov/iStockPhoto
Additional images courtesy of Neiman Marcus