Men’s fashion in 2016 moved between sharp tailoring and casual ease, with loafers bridging formal and everyday wear, bomber jackets cropped at the waist for clean proportions, and tweed three-piece suits adding texture in brown tones.
The choice depends on whether your workplace allows chinos and sweaters where suits once held, a shift that reached J.P. Morgan and spread from tech offices led by Mark Zuckerberg in jeans.
1. Loafers
Tassel loafers sit between casual and formal in a way few other shoes manage. The tassels add detail without drawing attention, and the slip-on silhouette works with trousers that have a sharp crease or a relaxed break.
Black leather is the safest choice.
It reads professional with grey pinstripe or charcoal wool, and still works with dark denim if your jacket and shoes stay sharp. Brown and burgundy loafers feel more casual and pair better with lighter fabrics or less structured trousers.
2. Bomber Jackets
A bomber jacket gives you outerwear that moves between settings without needing much thought. The ribbed cuffs and hem hold the shape close, and the cropped length keeps proportions clean when you layer over a hoodie or crewneck.
Black works with almost anything.
Pair it with black jeans and white sneakers for a monochrome look that feels intentional, or break it up with grey or olive trousers. The fit should close at the waist without bunching, and the shoulders should sit flat.
3. Destroyed Jeans
Destroyed jeans split opinion, but in 2016 they showed up often enough to count as a real option. The rips and fraying give texture, and the worn-in look pairs best with clean, simple pieces elsewhere.
Black destroyed denim feels less obvious than light blue.
The sneakers should stay low-profile so the jeans carry the weight of the outfit. If the distressing runs heavy, balance it with solid colors and no competing patterns.
4. Track Pants
Track pants moved out of the gym and into everyday outfits, usually in colors that felt more deliberate than grey or black. The side stripes add contrast, and the tapered leg keeps it from looking sloppy.
Brown track pants with white stripes sit in an unexpected space between athleisure and street style.
Pair them with a fitted t-shirt and slides for a casual look that still feels put together. Avoid baggy tops; the pants already have volume.
5. Checkered Clothes
Checkered shirts cover a lot of ground: small gingham reads preppy, larger checks feel workwear, and tartan leans traditional. The pattern adds texture without needing layering, and it breaks up solid-colored outfits.
Brown and tan checks pair well with light-wash denim, especially if the jeans have distressing that stops it feeling too polished.
Keep the sneakers neutral. If the shirt runs oversized, tuck the front or leave it open over a plain t-shirt to tighten the silhouette.
6. Turtlenecks and Mocknecks
A turtleneck under a leather jacket is one of the cleanest layering moves you can make.
The high collar fills the space at the neckline without adding bulk, and the fit stays slim enough to sit under structured outerwear without bunching.
Black on black works because the textures differ: smooth knit under matte or grained leather.
Grey trousers lighten the lower half and keep the outfit from reading too heavy. If you go with a mock neck instead of a full turtleneck, the collar sits lower and feels less formal.
7. Clothes with Bold Patches
Patches break up solid fabric and give a jacket detail that feels personal without needing tailoring. High contrast and enough coverage make a patch read clearly instead of disappearing into the base fabric.
The effect works best when the base garment stays simple.
A textured jacket in one color lets the patches carry the visual weight. If you layer this over a plain t-shirt and keep the trousers neutral, the jacket does all the talking.
8. Cable-Knit Sweater Layered Look
Cable knit adds texture and weight to a sweater without making it feel heavy. The raised ridges catch light differently than flat knits, and the cream color here softens the outfit enough to feel approachable.
Layer it over a collared shirt so the collar and cuffs show.
Light blue works because it sits close to cream in value but still gives contrast. The fit should allow the shirt collar to sit flat under the sweater without bunching at the back.
9. Vertical Striped Button-Down Shirt
Vertical stripes lengthen the torso and work best when the stripe width stays narrow.
Brown stripes on a tan or beige ground feel warmer than the usual navy or grey, and the color makes the shirt easier to pair with earth tones.
Beige trousers in the same value as the shirt base keep the outfit cohesive without matching exactly.
The fit should stay slim through the body so the stripes run clean and uninterrupted. If the shirt runs long, a half tuck at the front keeps it from looking sloppy.
10. Classic Navy Tailored Suit
A navy suit in a tailored cut is the most reliable formal option you can own.
The color stays neutral enough to work with most shirt and tie combinations, and the structured shoulders and slim lapels give it a shape that holds up across settings.
Pair it with a striped shirt and a tie that picks up one of the stripe colors.
The stripe spacing here is narrow enough to read as texture rather than bold pattern, so it does not compete with the suit. Brown leather shoes and a matching belt finish it without pulling focus.
11. Tweed Three-Piece Suit
Tweed in brown tones gives a three-piece suit texture and warmth that smooth wool does not. The fabric weight makes it better suited to cooler months, and the waistcoat adds formality without needing a tie.
Tweed works with leather brogues or derbies in tan or dark brown. If you wear this for an event, keep the shirt plain so the texture of the suit stays the focus.
Casual Work Attire
Workplaces in 2016 shifted toward dress codes that allowed chinos and crewneck sweaters where suits once held.
J.P. Morgan relaxed its standards, and tech leaders like Mark Zuckerberg wore t-shirts and jeans to flagship events, spreading the startup approach to offices that had long required tailoring.
The change did not mean sloppier dressing.
It meant taking tailored trousers and pairing them with a leather bomber, or wearing a blazer over jeans with a plaid shirt and white sneakers. The structure stayed, the formality dropped.
If your office allows it, build around pieces that hold their shape.
Chinos in grey or navy replace suit trousers, and a sweater in cashmere or merino sits where a dress shirt used to. Add a bomber or blazer when the situation asks for it, and keep the shoes clean.
Mixing Styles
Mixing a blazer with jeans or pairing tailored trousers with a bomber jacket became a reliable approach in 2016. The formal piece holds the outfit together, and the casual one keeps it from feeling stiff.
A blazer over a plain t-shirt and dark jeans works if the fit stays slim and the shoes are clean.
White sneakers or leather derbies finish it without needing dress shoes. If you add a plaid shirt, keep the pattern small so it reads as texture.
Trousers in grey or navy pair well with a bomber in black leather.
The proportions stay balanced because the bomber stops at the waist and the trousers hold a crease. A crewneck sweater under the bomber adds a layer without bulk.
The method is straightforward: one piece from each side, fitted well, with shoes that match the cleaner half.
Color Trends
Grey and pink showed up often enough in 2016 to feel deliberate. Grey stays neutral and pairs with almost anything, while pink adds warmth without reading as bold.
A grey suit with a pink shirt softens the formality and works for offices that allow color.
The pink should stay muted, closer to dusty rose than bright coral, so it sits comfortably under a jacket. A grey tie in the same value range keeps the palette cohesive.
Grey trousers with a pink oxford shirt feel more casual and pair well with brown leather shoes.
The shirt can stay untucked if the hem is short enough, or you can tuck it and skip the belt for a cleaner line.
The combination works because neither color demands attention. They sit next to each other without competing, and the result feels put together without much planning.
Frequently Asked Questions
What clothes did men wear in 2016?
Men wore bomber jackets, destroyed jeans, track pants, and turtlenecks layered under leather jackets. The year mixed casual athletic pieces with tailored items, and checkered shirts and cable-knit sweaters appeared often enough to define the look.
What to wear to a 2016 party as a guy?
A black bomber jacket over a grey crewneck or a turtleneck under a leather jacket both work for parties.
Pair either with dark jeans and low-profile sneakers, or go more formal with a navy tailored suit and brown leather shoes if the event asks for it.
