How to Wear a Bow Tie for the First Time

Ackee Tree Clothing  ·  Derby Style  ·  First-Time Bow Tie Guide

The first time someone wears a bow tie for Derby, the real hesitation is rarely the bow tie itself. It is wondering whether it will feel natural once everything else is on.

Every Derby season someone messages me who has never worn a bow tie in their life and has decided that this is the year. Sometimes it is the man himself. More often it is his wife or partner who has already picked the bow tie and is now trying to make sure he actually wears it correctly.

One customer stands out. He had ordered a self-tie bow tie, which seemed like a good idea at the time. The night before the event he pulled up videos and spent what he described as a frustrating evening trying to learn. His wife tried. He called friends. Nobody knew how to tie a self-tie bow tie.

 They ended up bending the self tied bow tie into a shape that looked close enough, pinning it so it stayed, and then pinning that to his shirt. It looked fine in pictures. But he knew. That gap between how it looked to everyone else and how it felt to him is exactly what this guide is about.

Pre-tied and self-tied are not the same thing, and that is the point

People sometimes assume a pre-tied bow tie is just a self-tied one that someone else finished ahead of time. Not quite. The classic pre-tied bow tie has a formed, set shape that looks consistent every time you put it on. A self-tied bow tie produces something slightly different each wear.

That uniqueness is what the purists love. I follow an allergist on social media who has an extraordinary collection of bow ties and wears self-tied almost exclusively. You can tell from how he wears them that the tying is part of the ritual for him. He takes the time, he gets it right, and the result reflects that.

But for the average person getting ready for Derby Day, often in a hotel room and often running late, go pre-tied and save yourself the headache.

A pre-tied bow tie is not settling

There used to be a feeling that wearing a pre-tied bow tie meant you could not handle the real thing. That thinking is mostly gone now. The average modern guy wants to look good, feel comfortable, and not think about his neckwear once the first mint julep is poured.

A well-made pre-tied bow tie looks completely intentional in photographs, which is where most Derby memories actually live. The adjustable neckband fits most collar sizes and takes under a minute to put on. Set it once, walk out the door, and it will look just as polished at 6 p.m. as it did at brunch.

How to wear a pre-tied bow tie for the first time

Step 1: Start with the right size for your frame. A standard 5"x3" pre-tied bow tie flatters most builds and gives the right visual presence for Derby photos and crowd settings.

Step 2: Button your shirt all the way to the top. The bow tie sits at the collar button, so if that button is not fastened the whole thing will sit wrong.

Step 3: Feed the neckband under your collar and fasten the clasp. Adjust until it feels secure but not tight, then flip the collar down over the neckband.

Step 4: Check the mirror from a normal standing distance, not six inches away. From the distance people will actually see you, a good bow tie reads exactly the way it should.

Step 5: Leave it alone for the rest of the day. A pre-tied bow tie holds its shape. Trust it and move on.

Learning the self-tie when you are ready

Tying a bow tie is a real skill, and like most skills it is easier to learn when you are not doing it for the first time the night before an event. If you are serious about wearing a self-tie, start practicing at home weeks before Derby.

How to tie a self-tie bow tie

The Navy with Pink Horses self-tie is a good one to learn with because the print stays readable through the folds.

Step 1: Set the length before you put it on.

Step 2: Cross the longer end over the shorter end.

Step 3: Fold the shorter end into a bow shape.

Step 4: Drop the longer end over the center.

Step 5: Fold the longer end and push it through the back loop.

Step 6: Adjust and stop. The slight irregularity is what makes a self-tie look right.

The pink horses on navy stay readable through the folds once the bow is formed. The print does not disappear when the fabric bunches, which is one reason this fabric works especially well as a self-tie.

The same customer, one year later

The customer who pinned his bow tie that first Derby came back the following season. He had been practicing at home. He ordered the self-tie again, and this time he knew what he was doing. That shift from improvising in a hotel room to walking in confident the next year is what happens when you give yourself enough time to actually learn it.

Planning your first Derby look? Tell us in the comments what colors you are wearing this year.