First Lady Style Trends Defined Create Your Own Timeless Look

by Meredith Sassoon

Alright y’all, buckle up ‘cause this whole “First Lady Chic” experiment got messy before it got good. Here’s how I butchered it before kinda, sorta figuring something out.

First Lady Style Trends Defined Create Your Own Timeless Look

The Pinterest Trap & Wishful Thinking

Saw those elegant pics – Jackie O suits, Michelle’s sharp dresses, Melania’s fancy coats. Looked effortless, right? Thought, “I got a black blazer somewhere. How hard could this be?” Big mistake. Dug out the blazer. First problem: it smelled faintly of old coffee and dust bunnies. Second problem: paired it with my regular jeans and t-shirt. Looked like I forgot my name badge for a conference I wasn’t attending. Zero elegance, max awkward.

Thrift Store Shenanigans & Reality Check

Decided I needed the “timeless staples.” Hit up the thrift store feeling ambitious. Grabbed things that looked fancy:

  • A silk scarf with horses on it (thought it looked Hermès-ish from afar).
  • A stiff, boxy skirt suit in a lovely shade of “grandma’s couch.”
  • Some pointy-toed pumps that promised blisters in 5 minutes flat.

Got home, all excited. Put on the suit. Felt like cardboard armor. The scarf? Tried three ways. Looked like a bandage, then a weird bib, then just… lost. The shoes? Yeah, couldn’t even walk properly to the mirror. Felt ridiculous, not refined.

The Tipping Point & Ditching the Rulebook

Almost gave up. Threw the itchy scarf on the chair. Stared at that awful suit jacket. Then got annoyed. Why was I trying to be them? My life involves coffee spills and walking the dog, not state dinners. So, I started playing mix-and-match with my own stuff.

First Lady Style Trends Defined Create Your Own Timeless Look

Pulled out my best dark jeans – the ones without rips. Found a simple, good-quality white tee. Put on the dusty black blazer, but rolled the sleeves up rough. Skipped the awful pointy heels – wore my clean white sneakers instead. Remembered the stupid horse scarf? Used it once, tied loose like I didn’t care. Added tiny gold hoops I wear all the time.

The “Ah-Ha” Moment (Sort Of)

Looked in the mirror. Not a First Lady. But kinda… polished? Comfy? Like me, just slightly upgraded? Walked to the kitchen – no blisters. Leaned over to grab coffee – no choking feeling from a stiff collar. The messy bun stayed put. That was key. It wasn’t about copying their exact outfit. It was grabbing pieces that felt solid and clean from my closet. Forget the “rules.” Turns out, for me, “timeless” means:

  • Feeling comfy enough to actually live your life.
  • Keeping it stupid simple. One good piece elevates the basics.
  • Wearing YOUR shoes. Seriously, ditch the painful ones.
  • Little touches you like (the hoops!), not what some guide says.

Did I achieve instant elegance? Nope. But I looked put-together without feeling like a stiff mannequin. And honestly, that’s way more timeless for my real world than any fancy hat. Lesson learned: steal the idea of looking polished, not the literal outfit. Now, where’s my coffee?

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