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Acing Your Accessories: Top Tips for Men's Style

To be perfectly honest, men’s accessories are tricky, and accessorizing really well requires you to choose one of two paths, which we’ll call the Perfect Gentleman and the Style Original. It’s the difference between Matt Bromer dressed as the impeccable Neal Caffrey, and Matt Bromer breaking all of the standard style rules for the red carpet in Monte Carlo.

matt bromer style and accessories

And while it never hurts to look like a Hollywood star, there is one essential element that that pulls both looks together, and that is absolute confidence. If Matt Bromer looked in any way nervous or the least bit apologetic for wearing three different prints and pairing the outfit with spats, he would have been crucified by the fashion press—but he makes the implausible look effortless.

There are few things sexier than the unshakable conviction that you look amazing.

The Perfect Gentleman: Elegance and Balance in All Things

Dressing well is a form of good manners – Tom Ford

men's classic look

You know this look—this is the classic look that you’ll see in almost any memorable movie dated before the 1960s, where men let their tailoring and their posture do most of the work. Their clothes are understated, and their accessories (with the occasional exception of a jaunty pocket handkerchief or tie) always match perfectly. Think iconic men’s fashion: Clark Gable, Jimmy Stewart, Cary Grant, Gregory Peck.

Clark Gable, Jimmy Stewart, Cary Grant, Gregory Peck dress styles

You can see this look updated today on the red carpet, and in the day-to-day look of fashion-conscious guys like Tom Cruise, Hugh Jackman, Pierce Brosnan, and Daniel Craig. The fabrics are more sleek, but the concept is largely the same: strong lines, solid colors, effortless masculinity.

modern movie star dress styles

The handy thing about this wardrobe is that once you’ve got the basics, you really can’t go wrong. It’s based on a like-to-like matching system.


  • Match Leather-to-Leather: If you have a brown pair of shoes, you should have a brown belt, and (as appropriate) a brown briefcase/bag and brown leather gloves. (Ditto: black.) You would never match suede with patent leather.
  • Match Metal-to-Metal: If you have silver accents on your shoes or hat, you should be wearing a silver belt buckle, and a silver watch. Your complementary briefcase or bag should also have silver clasps/buckles. The shine should match too—you don’t want polished silver with a scuffed pewter.
  • Not Too Many Colors: The whole look is defined by two, maybe three, colors, including black and white. The flair comes from the outfit’s exquisite cut and your total self-confidence, not from ostentatious, eye-searing fashion originality.
  • Color Families: The colors that you wear should be predominantly (if not exclusively) solids, and complementary. If you’re wearing a suit, your jacket and pants should always match precisely. Shades of brown, black, and blue probably dominate your wardrobe, with the occasional splash of burgundy or red.

Requisite Accessories:

  • Classic hats (think fedora—baseball caps and beanies need not apply) 
  • Winter scarves (long and elegant; worn as the only splash of color over an otherwise monochromatic outfit)
  • Sleek ties (no whacky prints) and pocket handkerchiefs
  • Cufflinks and tie clips (expensive and understated—err on the side of simplicity)
  • Leather gloves (black and brown)
  • Pricey watches (in gold/bronze and silver)
  • Full-grain patent leather belts (minimum of four—black and brown with gold/bronze and silver buckles respectively) 
  • Extremely slimline leather wallet (matched to leather of shoes/belt)
  • Leather shoes (black and brown) 

Overall Feel:

Timeless, Elegant, Quintessentially Masculine.

The potential downside of this look is that it’s invariably expensive. There’s no flash to hide behind, so the elegance of the outfit lies in the perfect fit and high-quality fabric. No one ever mistakes a custom-tailored Armani for an off-the-rack suit from JC Penny.

The Style Original: Never Lost in the Crowd

It is better to fail in originality than succeed in imitation - Herman Melville

This is an advanced style choice, because if you fail to pull it off, you’ll look like a complete lunatic; but, either way, people will remember your style forever. Fresh Prince of Bel-Air, anyone?

fresh prince of bel-air style

There have always been fashion leaders who were also fashion outliers. In the 1930s, that would have been Errol Flynn. His bold decisions to mix fabrics and contrasting prints, to incorporate more colors and patterns, all resulted in a look that definitely stood out from the monochromatic crowd…even when he wasn’t dressed in tights and thigh-high boots.

Errol Flynn fashion and accessories

In more modern terms, this look translates into some of the more eccentric offerings worn by stars like Donald Glover, Jared Leto, Johnny Depp, and Tinie Tempah.

eccentric clothing styles

Note: for those of you in relationships, remember that there can only be one fashion-extraordinary look per couple. So, save your more interesting outfits for a time when your partner is willing to go with color and style simplicity.

couples clothing choices and style


  • Look at Women’s Wear: Think about fabrics, colors, embroidery, and patterns that are usually reserved for women. Can they be adapted for the traditional menswear cuts?
  • Accessorize Creatively: Summer scarves, bracelets, necklaces, piercings. Consider layering your accessories.
  • Mix Genres: Suits with sneakers. Beanies with formalwear. Summer prints on winter clothes.
  • Go Bold: Lean on powerful colors and strong contrasts.
  • Think Archaic Accessories: Consider bringing back showy pieces that were more common in previous generations of men’s fashion—top hats, watch fobs, and canes can be style stand-outs, especially if you go for non-traditional colors.

Accessories Options:

  • Consider the full range of hats—from beanies to bowlers. 
  • Consider winter and summer scarves—and consider pairing them with unlikely or off-season outfits.
  • Ties worn loosely; maybe replaced by ascots, or lightweight scarves
  • A crossbody bag or backpack can accent this look. 
  • Remember that conventional watches can be replaced by bracelets or layers of bracelets.
  • Belts and shoes in stand-out colors, or in subdued colors to better draw attention to some other part of your outfit.
  • Socks are optional, but only if you’re wearing super-comfy shoes.

Overall Feel:

Fresh, Punchy, Aggressive, Original.

It’s often the case that the more successful original looks take the classic menswear pattern, and then change just one or two things dramatically. If you go completely anti-classic (changing color, and print, and cut, and accessories), you tend to fall too close to the “Fashion Cautionary Tale” look. So before you get too crazy with your experimentation, remember the immortal fashion advice of journalist and author P.J. O’Rourke:

Never wear anything that panics the cat.

And, when in doubt, consider classic lines in bold colors—it’s the best of both words, because you get the strength of the traditional gentleman’s look, with the punch of the more original style offerings.

otero clothes for short men

Combining class and originality ...

Otero Menswear. The Perfect Fit.

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