Let Me Talk Fashion: Pros and Cons to Your Thanksgiving Day Outfit

Let Me Talk Fashion is our weekly installment going Two Buttons Deep into the do’s and don’ts of everyday fashion. As Joan Rivers’ self-proclaimed successor, it is my duty to help keep the world looking stylish and practical one Fashion Friday at a time. This week, we’re coming to you a few days early to help prepare your fashion choices for the holiday weekend ahead.

By the looks of the retail storefronts and people’s front yards, you might’ve already thought the holidays have came and went. Every year, the music starts playing sooner and the holiday decor goes up quicker (though you should probably assume your neighbors’ wreath has actually been hanging up since last Christmas). One thing you never seem to be able to plan too far in advance, however, is your holiday outfit. We can attribute to this to one of the following:

A. You’ve been dreaming about stuffing, roasted potatoes and pumpkin pie since Labor Day, and there’s nothing more important to focus on at this moment besides the food –not even what you’re wearing while you’re eating it (or napping in afterwards).

B. You don’t care what you look like in front of your family, so no forethought needed. There’s not a poncho big enough to hide the hangover you’ll be rockin’ at the dinner table.


So, I’m going to break it down for you to help carefully weigh your outfit options. There’s about three ways we can take it without going overboard here, but there are some pros and cons to each that are definitely worth considering.

Option 1, Dress to impress

Guys: Slacks, a nice pair of Chelsea boots or dress shoes and a button down shirt with a warm, fall cardigan over top |  Gals: Tall boots with a heel, a dress or skirt with subtly-patterned tights and a festive statement necklace


  • You’re classy and using a good excuse to wear your underused, dressy clothes
  • You can count yourself out for running around with small children or getting roped into an awkward “promise it’s not tackle” family football game
  • It’s an easy transition into a social gathering post-dinner at a bar or friend’s place


  • Anything tight (stockings or a slim-fit button down) might feel a little more snug after your big meal, not to mention uncomfortable for that post-dinner nap
  • It’s always a nightmare trying to enjoy your food while battling paranoia of spilling cranberry sauce on your crisp white shirt or favorite sweater
  • Small children or family pets add another hazard to keep from ruining your getup

Option 2, Minimal Effort

Guys: Stylish sweatpants (like joggers) paired with a graphic tee and a crewneck sweatshirt. Semi-dirty sneakers and maybe some mismatched socks underneath. | Gals: Black leggings, of course, with a dramatically-oversized sweater that covers the bum. Comfy boots or trainers and a thick, wraparound scarf to accessorize.


  • You put little to no effort into your outfit, which helps minimize the thinking while you battle the Thanksgiving Eve hangover
  • You’re ready to play dirty in the family games or carry a toddler on your shoulders
  • Comfort is key and this outfit allows you to consume infinite bread rolls


  • Your semi-sloppy look could cause some buzz during family small talk
  • “Look good, feel good” applies so if you don’t look great, you’re going to be feeling extra sluggish and not up for any social events after the mandatory gathering

Option 3, Classic and comfortable

Guys: Jeans rolled up with a cuff to expose some stylish fall boots or loafers. An unbuttoned flannel shirt with a fresh, clean Henley top. | Gals: Jeans with a more fitted sweater on top and a festive accessory –a blanket scarf, stacked bracelets or chunky earrings.


  • You leave the house feeling good about what you wear without being over the top
  • The outfit also works for a cozy hangout a friend’s house, or transitioning to spend time at your significant other’s family gathering
  • It’s still comfortable while portraying some class and thoughtfulness to the look
  • No matter if your event is dressy or super casual, you still fit right in


Well damn, no wonder why we’re closing out the post with this look. Honestly, #3 is the best way to go for your Thanksgiving holiday in this fashionista’s opinion. I can’t find any cons here. Any time you’re in front of a group of people –friends, family, coworkers, etc. you want your look to look effortless, yet carefully crafted. Each look here gives you an opportunity to be comfortable and classy while showing off some bits and pieces of your personal style.

But hey, it’s your holiday. No one knows the vibe of your family gathering (or the severity of the hangover) better than you do. I can just guide you in the most fashion forward direction possible –and that’s a journey that I’ll never quit trekkin’ along on.

(PS: Thanks, Pinterest, for all the example outfits.)



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