Moving up from Small/ Medium/ Large Dress Shirt Sizing

Are you still buying shirts that are only "roughly right?" Small/Medium/Large worked fine when you were wearing tee shirts and hoodies. But it's time to step up because first impressions matter. Poorly-fitting shirts put you at a disadvantage vs. your better-dressed peers. People will notice. Here's the good news: you're about to learn how to show up with shirts that fit in all the right ways.



Let’s establish what “good fit” looks like in a dress shirt:

  • Most guys wear ties only occasionally, but when you do, the collar should be comfortable.  Don't go overboard and show a large gap between your neck and the collar.
  • Your sleeves should cover your wrist, and show a bit of cuff from your jacket.
  • The body of the shirt should compliment your body: not baggy, but also not popping buttons

Here’s the good news: ~90% of guys can find a good fit without needing custom tailoring. Knowing your collar and sleeve measurements will get you most of the way there.

Finding a store that has your size, not just their size

Most store associates can get you started by taking the measurements you will need to find a great fit. However, there’s a complication: they’re looking for the best item for you in their store, not necessarily what's best for you. If you’re lucky enough to be a “body double” of the sizing models they use, you’ll be fine. If not, you should walk out the door and shop somewhere else. Seriously: wearing a poorly-fitting shirt makes a bad impression, and it's totally avoidable.

Dress shirt brands take three different approaches to sizing:

"Small/Medium/Large" approach is great for tee shirts and hoodies. These retailers usually offer "Tall" versions to serve guys with longer arms and end up with ~7 sizes. This is much easier for them to manage inventory, but may not fit your body well, unless you're one of their 7 chosen sizes.  Examples: Banana Republic, J. Crew, H&M, Uniqlo

Exact Neck sizes in ½” increments and sleeves in 2" increments, with a total of ~20 sizes. Examples: Hugo Boss, Kenneth Cole, Ralph Lauren, Tommy Hilfiger, Calvin Klein, Van Heusen

Exact Neck & Sleeve sizes in ½” neck increments and 1” sleeve increments, with a total of over 30 sizes. Examples: Jos. A Bank, Brooks Brothers, Amazon Buttoned Down, Nordstrom, Charles Tyrwhitt

The more sizes a retailer offers, the better the chance that they something that will help you look great. BTW, if you shop the right way, you can find Exact Neck & Sleeve shirts for about what you would pay at S/M/L retailers.

Still dreading going shopping? Join 90% of men in America! Most men grit their teeth and go to a store, where they waste hours getting an "okay" solution. Walking back to the parking lot, they wonder if they're walking past something even better, but they just don't have the energy to go on.

If you already know your basic measurements, there's a dramatically better way to go. A service that searches over 700 sizes from 14 top brands in seconds. A personalized assortment that fits the way you want, available online today. At no mark-up from brand’s website pricing.

If you need to learn your basic measurements, check out our measurement guide.

Free search for shirts that fit your body and your budget
Mark Hill

My name is Mark, and I’m the Founder & CEO of The Wardrobe Essentialist. I've spent my career in business and business casual offices, initially at Bain & Co in Boston and San Francisco, and then as a Business Unit General Manager at global Fortune 500 companies.

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