Accessories are to fashion what Dennis Rodman and Scottie Pippen were to the Chicago Bulls: Seriously stylish role players. Watches, belts, and pocket squares can transform a look from straightforward to slam dunk. But accessorize with caution. The wrong accessories are much, much worse than none at all—think neon bandannas, oversized clock necklaces, and multiple gold chains. (We’re looking at you, Mr. T.)

To keep you on the straight and narrow, we’ve assembled this Summer 2011 guide to timeless accessories, trendy accessories, and the accessories to straight-up avoid. Gentlemen, start your engines.

SUNGLASSES

A wardrobe essential. To find the pair that suit you best, look for shades that are proportional to your face shape. Rounded sunglasses work well on square faces, while angular shapes suit rounder faces best.

Timeless: Trapezoidal (ie: Wayfarer-like) tortoiseshell frames.
Persol 2988-S sunglasses ($296, iloristyle.com).

Trendy: Round tortoiseshell frames.
Persol 2994-S sunglasses ($296, iloristyle.com).

Avoid: Red lenses. Oversized rectangular frames. Embellished arms.

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WATCH

People will assume your watch offers clues to your personality. Brand names might impress the crowds, but it’s your opinion that matters most. Choose a watch that you’ll love and wear for years.

Timeless: A leather strap with a round face and sterling silver detailing.
Longines watch, Heritage Collection ($2,100, longines.com).

Trendy: A super sleek timepiece with bold orange accents.
Omega Seamaster Planet Ocean 45.5 mm watch ($8,000, omegawatches.com).

Avoid: Excess bling. Anything that could be called “delicate.” The urge to ever utter the words “A hair past a freckle” when asked for the time.

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BELT

Supremely functional, the right belt can also complete your look. Unless you’re a serious clotheshorse, skip colour, and stick with neutrals like brown, black, and grey.

Timeless: Elegant brown leather with a silver buckle.
D&G leather belt ($175, harryrosen.com).

Trendy: Brown leather with cool chain detailing.
John Varvatos Star USA chain belt ($125, harryrosen.com).

Avoid: Fake leather. Novelty buckles. Belts that are too long, or worse, too short.

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We give you the ins and outs on how to wear a tie, pocket square and socks on the next page…

TIE

You’ll be getting these as gifts for the rest of your life, so may as well amass a collection you can be proud of. Create a stable of solid colours and classic patterns—stripes, checks, plaid—then add in a few creative showstoppers.

Timeless: A brightly coloured silk with a subtle pattern.
Eton Neat ties ($125 each, harryrosen.com).

Trendy: Paisley pattern in a hot hue. Etro ties ($160 each, harryrosen.com).

Avoid: Where’s Waldo. Tweety. Piano keys.

POCKET SQUARE

The ultimate gentleman’s accessory is back in style. Brush up on how to fold them here [http://www.youtube.com/watch?v=Y2gIENStLJg].

Timeless: As with ties, a trifecta of silk, vivid colour, and tasteful pattern.
Salvatore Ferragamo Yellow Chain pocket square ($64.99, harryrosen.com).

Trendy: A statement pattern with a vintage travel poster vibe.
Etro Retro Getaway pocket square ($98, harryrosen.com).

Avoid: Using it as a handkerchief. Matching your square exactly to your suit (use your tie as a guide instead).

SOCKS

Enough said. Or is it? Two points: Opt for dark colours. And your pants should be long enough that your socks only show when (if?) you cross your legs.

Timeless: Understated stripes.
Boss Black striped dress socks ($22.50, harryrosen.com).

Trendy: Minimalist stripes with colourful lavender accents.
Boss Orange Malibu Blue argyle sock ($17, harryrosen.com).

Avoid: Holes. Mismatched pairs. White gym socks, outside of the gym.

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Check out the do’s and dont’s of cufflinks and jewellery on the next page…

CUFFLINKS

Cufflinks are the sartorial equivalent of an espresso: Something small that packs a major punch.

Timeless: Black, silver, medieval-inspired.
GreenShag Black Griffin cufflinks ($80, greenshag.com).

Trendy: White, green, automobile-inspired.
GreenShag Green Convertible Sweet Ride cufflinks ($80, greenshag.com).

Avoid: Naked ladies. Taz. Cufflinks larger than a quarter.

JEWELLERY

Choosing the right jewellery will likely be your toughest accessory challenge. Focus on finding pieces that have both polish and personality. A simple starting point? Silver, titanium, and platinum—easier to pull off than gold.

Timeless: A sophisticated cuff.
Tiffany & Co. Atlas Cuff in titanium and sterling silver ($875, tiffany.com).

Trendy: Edgy dog tags.
Tiffany & Co. Double Tag Pendant in titanium and sterling silver ($485, tiffany.com)

Avoid: Coloured rubber bands representing worthy causes. Piercings, on ears and elsewhere. The aforementioned gold chains and clock necklaces.

Read more
Men’s fashion: 5 easy pieces for a summer wardrobe
Men’s fashion: Summer essentials
The best accessories for men