How I Build my Wardrobe with Designer Pieces (on Major Sale)

There’s an art to curating a wardrobe that feels both timeless and unmistakably you—and it rarely involves impulse-buying the latest trend at full price. Instead, I treat each change of season like a treasure hunt: the moment those coveted end-of-season sales hit, I scour the racks (and my bookmarks) for the kind of heirloom-worthy pieces that are now 50–80 percent off. By bringing home just one or two gems at the end of each season—think an Oscar de la Renta cocktail dress, an Emilia Wickstead skirt, or a Chloe blazer—you’ll find that in only a couple of years your closet is dotted with garments that aren’t just beautiful, but something your daughter or granddaughter will want to inherit as sentimental reminders of the celebrations you enjoyed while wearing them.

The great thing about building a timeless wardrobe is you don't need the latest thing, in fact, you can wait until the season is over to snag something truly special at the right price, and enjoy it for years to come. A few questions I ask before purchasing a designer piece of clothing: Does it have staying power? Is the design something that will feel relevant after a decade or more? Will it still flatter me as I age? Am I truly drawn to this piece or just tempted by a deep discount? Can I style it in multiple ways and for multiple occasions? These questions help steer me away from impulse purchases and towards pieces that are worth the investment.

I bought the Oscar de la Renta dress above (sold out but similar here) while pregnant and had to wait a full year before I fit in it, but it's been a treasured piece for everything from family trips to Nantucket to dinners with friends, and it's one of the pieces I get asked about the most. Click to discover some of my past designer clothing finds from Oscar de la Renta, Etro, Erdem, or Emilia Wickstead, styled in different ways to change with the seasons. (I'll do another post on bags because I have a slightly different approach to them!)

Below you'll find my current roundup of timeless designer finds at deep discounts - putting this together is an occupational hazard. I have so many pieces from this post in my cart right now!

The Outnet is one of my top places to score designer finds, they had direct relationships with many of the designers they carry and have the best selection of past season pieces. They're part of the same parent company as Net-a-porter, and have the same incredible customer service and lightening fast shipping. Plus, new customers get 15% off all orders, and 20% off new orders with code "HITHERE"! Here are a few of my top picks:

• This timeless black cocktail dress has dramatic draping at the bodice, and can transition effortlessly from an evening at the ballet to a holiday party.
• Suede drivers are a fall staple, and I just snagged these iconic loafers in olive for fall foliage road trips, coffee runs and everyday errands. SO chic!
• A floaty long-sleeved midi dress is one of my go-to pieces for everything from a day full of meetings to romantic dinner dates. They look great with heels or knee high boots, proving to be a go-to outfit when the temperatures dip.
• This Missoni dress will be something your daughter steals from you.
• This asymmetric blazer is both elevated and relaxed due to it's drapey knit and striking gold embellishment. I'd pair with a simple black tee and tailored trousers for everything from board meetings to holiday parties. I'd pair with these slingbacks (I own and love them in another color!)
• This cream number would be dreamy for a bride-to-be, at a baby christening, or with gold heels for a gala!
• This minidress is such a statement and not for everyone but I love it?! Since it's short I'd wear with flats like this.
• I love silk maxi skirts for year-round styling and this one is so chic - all you have to do is pick your favorite color!
• Oscar de la Renta is the king of floral sundresses, and a few others that caught my eye include this, this. And for dressier options I love this and this!
• This ethereal white gown would be perfect on a vacation in Greece, or for a bohemian bride.

Other finds from around the web:

• Nili Lotan makes high quality, timeless wardrobe staples and since they have such a premium pricetag, I always try to buy their pieces on sale. A few favorites right now include this gorgeous collarless jacket, this boxy jacket and I just bought this cable knit aran sweater (worn here) that reminds me of one Grace Kelly wore. (The sweater sleeves are long and the body is a tad cropped, it's better for taller gals.) This silk tie-neck blouse is another fab sale find, that would look wonderful with everything from jeans to a pencil skirt!
• Emilia Wickstead and Erdem are two British brands that make the loveliest dresses. A few special pieces include this olive cocktail dress, this floral denim dress, this feminine shirtdress, this tailored dress, this pink cocktail number (love!), this pink sundress, and this tinsel inspired cocktail dress. If dresses aren't your thing, how about this stunning wrap blazer?
• Etro's rich patterns always get me, and I especially love their skirts. This maxi skirt moves beautifully and pairs with a rainbow of tops - opt for tank tops in summer and turtlenecks in colder months. Similarly, this timeless-yet-fun shirtdress looks fabulous with flat sandals or knee high boots.
• If you have an eye towards deep fall/winter investment pieces consider snagging this Toteme clutch I own and love at 40% off (seen here and here!), this classic breton sweater, this cozy alpaca turtleneck, or this statement top which will have everyone asking "where did you get that?!"

And speaking of investment pieces that are an incredible value, you might spy something new and sparkly on my wrist. Lab diamonds have gotten SO good recently, and I'm testing out a few pieces that are wardrobe staples and will be sharing detailed reviews once I've had the chance to live with them for a month or two.

SHOPPING LIST: