I’m not going to sugarcoat it: when sale season hits New York City, I am all in. There’s just something about the way this city approaches a discount that feels unapologetically bold. Forget the cautious 20% or 30% reductions you see sprinkled across Europe during those first few weeks of markdowns. Here, sales don’t tiptoe onto the scene—they dive straight in. We’re talking 50% off right out of the gate, and not on random leftovers that have been gathering dust in the back room. No, these are the very pieces you’ve been coveting all summer long, the ones you thought you’d never snag before they sold out. Suddenly, they’re hanging there in front of you with a shiny red tag, practically begging to be taken home.
And if you’re anything like me, you already have a mental list of things worth the splurge once the discounts hit. So today, I’m sharing one category that deserves your full attention—one trend that isn’t just seasonal but set to carry you confidently into the next year. Ready? Let’s talk plaids.
Why Plaid, Why Now
Plaids—or checks, tartans, ginghams, however you prefer to call them—are having a serious moment. And I’m not just pulling that out of thin air; the runway receipts prove it. Balenciaga, for one, sent look after look in head-turning plaids down the catwalk, from oversized outerwear to tailored separates. Other designers have followed suit, treating this centuries-old pattern with fresh, edgy twists.
The beauty of plaid is its versatility. It can read preppy, punk, polished, or playful depending on how you style it. You can go all-in with a matching top-and-bottom situation (yes, I’ve done this, and yes, I stand by it), or you can keep it subtle with just one plaid piece paired with neutrals. Either way, the pattern speaks volumes without requiring much else to make a statement.
And let’s be real—if there’s one thing that makes a sale find truly worth it, it’s longevity. You don’t want to splurge, even at 50% off, on something that feels “so last season” before you’ve even cut off the tags. Plaids, however, are the kind of classic-with-a-twist investment that will keep earning their keep in your wardrobe long after the sales have ended.
How to Wear It: A Few Ideas
So, how do you incorporate plaid into your everyday rotation without feeling like you’ve been transported back to your school uniform days? Here are a few tried-and-true styling routes:
- The Coordinated Set
If you’re feeling bold, take a cue from the runways (and from my own experiment) and go for a plaid-on-plaid look. A matching skirt-and-shirt combo or a suit in full check is a statement maker, no question. The key is confidence—wear it like you mean it. Keep accessories minimal and let the pattern do the talking. - The Plaid Skirt + Oversized Knit Combo
Perhaps the most wearable way to embrace the trend: a simple plaid tube skirt paired with a cozy oversized sweater. Stick to solid knits in navy, cream, or even a bold jewel tone to balance out the busy print. The mix of textures—structured plaid against slouchy knit—creates an effortless contrast. Add boots and you’re set for everything from brunch to office days. - The Unexpected Accessory
Not ready to commit to head-to-toe plaid? Start small. A pair of plaid heels with an otherwise monochrome outfit can be surprisingly chic (and dare I say festive?). Or try a plaid bag, scarf, or beret for just a whisper of the trend. These little accents are often the pieces that get the most compliments because they feel fresh and unexpected. - The Outerwear Star
Winter coats are always an investment, but if you’re buying one during the sale, consider a plaid version. Oversized, belted, or sharply tailored, a checkered coat instantly upgrades even the most casual jeans-and-tee combo. Plus, coats in bold prints are easier to wear often than you think—throw it over a neutral outfit and you look instantly pulled together.
Why Sales in NYC Hit Different
Maybe it’s the competitive energy of the city, or maybe it’s just retail magic, but shopping during New York sales season always feels like a sport. There’s a thrill in finding that piece—the one you’d been lusting over for months—now within reach. And unlike other places where sales feel like an afterthought, here they feel like an event.
That’s why it’s smart to go into them with a strategy. Think about the pieces that will carry you beyond the season, the ones with staying power. A good plaid blazer or skirt is not just a holiday indulgence; it’s a wardrobe building block.
Final Thoughts
Sales can be overwhelming, especially in a city like New York where the options are endless and the markdowns are steep. But focusing on timeless-with-a-twist trends like plaid ensures that what you bring home won’t just sit in the back of your closet. It’ll work hard for you, season after season, adapting to whatever mood or occasion comes your way.
So when the racks start emptying and the frenzy of sale season takes over, remember this: plaids, plaids, plaids. Whether you go bold with a matching set, cozy with a skirt-and-knit combo, or subtle with a pair of heels, this is the one print that will keep you stylish long after the holiday shopping bags are put away.
Because at the end of the day, the real win isn’t just scoring 50% off—it’s knowing you snagged something you’ll love just as much at full price.
