The Young Gentleman’s Guide to Dressing for Thanksgiving Dinner

Well you did it. Graduated from college in the spring, got a job that uses that degree over the summer, and all through fall you’ve been buying your “first adult” everything. Now it’s Thanksgiving, the first holiday you get to go home and rub all of the above in your underachieving cousin’s face. You’re living the part, but do you look the part? It’s time for your “first adult” family holiday dinner, kid. But relax: We’ll show you how to pull it off.

Matthew in Taylor Byrd

If your Grandmother is anything like mine (hi Grammy!), she nixes wearing everyday jeans at thanksgiving dinner faster than you can say “pass the potatoes.” To a certain degree, Grandma is right. Everyone knows how you look in Levi’s 501s, but no one has seen you in a slim cords or denim that fit perfectly. This is the time to spend a few bucks and dress like your parents are proud of you. You’ll walk in and Aunt Linda, Uncle Jack and Grandma herself will turn their heads and say, “Now that’s what a successful young professional looks like!”

Adam from Southampton

To achieve the look, check out [eafl id=”81824″ name=”Old Navy Big & Tall Update Link” text=”Old Navy”]. This year their denim and cords have been upgraded surprisingly well. The best part is that their slim styles range up to a 48 waist online. Whether you choose denim or cords, you’ll look cool and still make Grandma happy. Just a reminder: “slim” and “skinny” are two very different things.

Remember those blousy button downs I mentioned before? Yeah … about those: Buy your size. Seriously. No matter what size you wear, look for a ‘modern fit’ rather than the more ubiquitous classic fit. Classic = what your dad will be wearing. Modern = exactly what you should be wearing. Fit starts at the shoulders. Keep an eye on the shoulder seams, they should line up with your actual shoulders (mind-blowing I know). Sleeves should be slim without being tight and the shirt should fall smoothly down your side and tuck in (yes tuck it in) without billowing out over your waist band. We’ve recommended Tailor Byrd before, and still do with great current styles.


Now look all the way down … to the floor. What do your shoes look like? Worn? Scuffed? Square toed? If you’ve answered ‘yes’ to one or more of the above questions, it’s time for a shoe intervention. Somehow over the past 10 years, guys have learned that the definition of a dress shoe is a square-toed slip-on. Erase that from your memory… like right now. They’re not what you should be wearing, ever, but especially with the type of look we’re creating. Shoes should be classic but updated to reflect the current style. The perfect combination is the penny loafer. (yes, they’re back.) It’s a versitile shoe that can take you from casual to more formal and they’re a great investment. We’re loving these updated classics from Calvin Klein.

Kynnedy's Office Style

Congrats! You’ve successfully made it through an article about how to dress for Thanksgiving dinner. Really, though, it’s more than that. It’s about looking the part you’re playing. A young professional who’s doing well in his career should look pulled together, on trend, but classic; because classic never goes out of style. I can’t guarantee it’ll get you to the adult table this year, but it’ll definitely increase your odds.

While we’re at it, here are a couple more options to up the ante:

  • Toss on a slim fit, solid color, cashmere sweater over the button-down. It adds another layer without the formality of a blazer or sport coat.
  • Try cuffing your pants up just a bit and going sockless with your loafers. Plus it’s always a million degrees in someones house around the holidays.
  • For shoes, when in doubt, throw on a brown driving moccasin. It goes with just about everything. Plus, it’s not a boat shoe. Everyone knows you like boat shoes.

This article originally ran 11/26/12 on

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