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How to tie up your style with this formerly nerdy accessory

Bow ties once clung to the extremes of nerd (Pee-wee Herman, Orville Redenbacher) or hero (James Bond, Winston Churchill), surfacing in the mainstream only for formal occasions (weddings, proms, black-tie affairs).

Edward Armah is a favorite bow tie brand among clients. Armah is known for unique designs. Trunk Club
Edward Armah is a favorite bow tie brand among clients. Armah is known for unique designs. Trunk ClubRead moreTrunk Club

Bow ties once clung to the extremes of nerd (Pee-wee Herman, Orville Redenbacher) or hero (James Bond, Winston Churchill), surfacing in the mainstream only for formal occasions (weddings, proms, black-tie affairs).

In recent years, they've been adopted by professionals and hipsters, proliferating from the office to the bar scene. While they are no longer the exceptions to the rules of cool, they can go awry faster than you can tie one on.

For those considering doing so this season, we consulted the experts for their pointers. Responding below are Adam Schoenberg and Cory Rosenberg, cofounders and co-CEOs of hook+Albert (hookandalbert.com); Michael Barkin, vice president of sales at Trunk Club (trunkclub.com); David Mutter, co-CEO of Beau Ties (BeauTiesLtd.com); Paul Kelley, a regional manager for Paul Stuart (paulstuart.com); and Allyson Wicha Lewis, vice president of merchandising for the Tie Bar (thetiebar.com).

Question: What width/size of bow tie is best for whom?

Hook+Albert: If you are wearing a skinny modern suit, the bow should be on the smaller side. If you are wearing a wide lapel, the bow can be a bit larger. We recommend matte fabrics: Wearing a bow makes a statement - the smaller the statement, the better.

Q: Must the bow be a perfectly symmetrical knot?

Paul Stuart: A slightly askew or unbalanced knot looks more natural and has a bit more attitude. Also, don't be afraid to create a very tight knot as that allows each of the bows to have deeper dimples, which looks beautiful.

Q: Is pre-tied or clip-on ever OK?

Trunk Club: It's OK if you are 3 years old or younger. Otherwise, I don't get it. In the same way that a to-be-tied bow gives a man an additional dose of appeal, a clip-on takes that masculinity away. Wearing a pre-tied bow tie only becomes worse if it's a brightly colored silk.

Q: Can a bow tie read casual?

The Tie Bar: Chambray bow ties, either solid or printed, give you that laid-back, cool vibe.

Q: Are bow ties a passing trend or timeless?

Beau Ties: We divide fashion into four basic stages: loyalist, fad, trend, and cultural shift. For most garments, there is always a small and extremely loyal group of aficionados that keep the flame burning. Suddenly, and usually led by students, the style is adopted and the look becomes a fad. Occasionally, fads evolve and spread beyond the early adopters and become trends. On rare occasions a trend spreads so wide and for so long that a genuine cultural shift occurs. This is exactly what has happened to bow ties.

Q: Do bow ties need a matching pocket square to complete the look?

Hook+Albert: No, just be confident with whatever one you pick. Basic rule: Don't worry about matching a pocket square with anything.

Q: Should bow ties be reserved for formal wear?

Hook+Albert: No. If you need or want to wear neckwear, a bow tie is less fuss, as it does not hang down. It is out of your reach all day.

Q: What are some of the freshest ways to wear a bow tie for New Year's?

The Tie Bar: To add a bit of luxe to your evening, try a velvet bow tie or swap out your typical black for a deep rich navy or oxblood. Another option is a knit bow tie in your favorite holiday color. The texture of the bow tie is both unexpected and on trend.

Q: What has changed since Churchill?

Paul Stuart: Years ago, most bow ties had a shiny silk finish in basic foulard prints. Now they've become more seasonal. For fall we featured wool/silk blend bows that have deep tones in a flat finish with more weight and substance to pair well with flannel suits and cashmere sport jackets.

Q: How shouldn't one wear a bow tie?

Trunk Club: Don't be the guy who unties his bow tie during an event and wears it hanging from his neck. That's a brutally classless look. Just take it off!