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March 10, 2022

A Definitive Guide to Wardrobe Investments

Post By:
Stacey Kovalsky
In-House Contributor
Vice President, Global PR & Communications
USPA Global | U.S. Polo Assn.
Guest Contributor:

You've likely heard the phrase "investment piece" while shopping online or in store. Maybe it’s when the salesperson puts the hard sell on you to get that high ticket item. She says “Ohhh, but it IS an investment. It will never go out of style and will always retain its value!” Well, she’s right. Simply put, this closet staple is something that may indeed come with a large price tag, but because of its timeless design and elegance, it could be worth the “investment” or splurge. 

Beyond the sometimes-hefty price tag, another way to figure out what type of item falls into the investment category is to evaluate if an item isn't season-specific or tied to a short-term trend that may be out of style quickly. Think: classic Chanel handbag, a quality leather jacket, a camel-colored all-weather trench coat, or elegant diamond earrings.     

Investment pieces truly are the basis of any smart, sophisticated woman’s wardrobe. Ideally, they can even be worn in multiple ways, whether alongside another classic or even complimenting modern trend.

No matter what it is, one thing is certain: investment pieces withstand time and trends. They are typically made of top-quality fabric that is durable or long lasting, and their design is classic and stylish. You may scoop up these items on a whim (like when Sex & The City’s Carrie walks into a department store and instantly falls in love with a pair of Manolo Blahniks). Or, it might be more financially practical for you to save up with your “eye on the prize” so that you can feel a bit better about dishing out a large chunk of change in one swoop.

Another smart way to go when making an investment in your wardrobe is the resale route. Look for that classic piece on a resale site like TheRealReal, Fashionphile, FirstDibs or Rebag. Not only can you often get amazing deals on gently used or even new products, but most of these sites even have buyback programs. A buyback program is when the site will guarantee to pay you about seventy percent of what you paid for the item you originally got from them, as long as it's in the same condition. With options like this, you can rest assured with your investment if you ever want to make a change or upgrade. 

I have gone ahead and curated the ultimate guide to fashion investment pieces, calling out (and linking) the splurge-worthy essentials you'll reach for year after year, plus I will give some tips and trade secrets on how to really tell what's an investment piece and what's not.

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Let’s start with one of my favorite categories…shoes. The footwear market is filled with timeless, investment-worthy shoes, so there is no doubt you can find the perfect pair to suit your very personal taste. From Gucci's classic loafers that just about every celebrity owns to Stuart Weitzman Nudist strappy sandals, and my all-time favorite, the Saint Laurent Tribute (now available in flats), be sure to shop top, iconic styles like these for a worthwhile footwear investment. If you love what you pick, you likely won't feel buyer's remorse because you’ll be able to wear them often, giving these styles a great ”cost per wear”. 


The options are endless when it comes to investment-worthy bags, but beware: this wardrobe essential typically comes with a large price tag. That's because many luxury designer handbags are made to be lifelong companions. Unlike trendy bags with all the bells and whistles or in wild colors and textures, timeless purses from brands like Chanel, Gucci, Fendi, Saint Laurant, and Louis Vuitton are made to last you years. Many will even fall into the vintage category after 10-15 years and still look nearly new, if well cared for. 

To find the investment bag that’s best for you, think about your needs. Do you want a bag that you’ll carry all the time (consider the Louis Vuitton Neverfull MM, Chanel Classic Double Flap or the Saint Laurent Sac du Jour), or one for a special occasion (like a Bottega Venetta Intreccato Pouch, the Dior Saddlebag or the Gucci Marmont)? 

Try to avoid flashy colors or trendy textures that may go out of style in the next year, or season. Look at price points you can manage and see what designers fall into that cost parameter. If you can’t really afford the bag you want, you can wait and save for it of course. But, also go to the resale sites I mentioned earlier. Do searches with the available filters. Are you comfortable with faint scratches on the handle of your Hermes? If so, you can likely get it for thousands less. For other luxe brands, you can save hundreds. But, if you genuinely want the experience of buying a special bag go to the store, talk with a consultant, try out many bags to be sure you make the right decision. Let them wrap and box it for you beautifully and walk out with that blingy shopping bag that screams “Yaaaaaaassss! I am worth every penny!”


When it comes to investment-worthy shirts, there are just a few things you should look for. First, quality fabric is key. Natural fabrics like silk, cotton, and linen last the longest and generally look the best. The silhouette is equally important. With style in mind, look for a shirt with clean-cut lines (think something modern and streamlined over anything with more of-the-moment detailing). You can never go wrong with a classic, tailored white cotton or silk shirt. Finally, when it comes to the price point, you can find great, timeless shirts without breaking the bank—check out Bloomingdale’s for amazing classic finds. 

If you want to take shirts to the next level, look for the comeback of the pussy bow blouse from Saint Laurent, Dolce Gabbana and other more reasonably priced brands like Hawes and Curtis


There’s absolutely nothing more classic than great-fitting jeans and a tailored blazer. And, there’s nothing more comfy than jeans and a cozy sweater! Needless to say, quality denim is crucial for any modern wardrobe.

When it comes to material, stretch fabric is oftentimes the most comfortable, though it can wear out more quickly, particularly after many washes (hang dry if you can). Typically a mid-rise jean is most flattering to all body types. When it comes to denim color, opt for a middle or dark wash- these are two classic options that will never go out of style. As cute as they may be, skip the acid-wash or ripped jeans for your investment pair as these styles go in and out of trend and don’t hold their place as an investment. 

You may be surprised at what designer jeans cost these days, but do yourself a favor and try them on to compare. If you feel and see the difference, then go with the one you love most- they are worth the investment!

For great fitting investment jeans, I love Rag & BoneFrame, and Mother and AGOLDE.


These days, the soulmate to a great pair of denim is the blazer.  The denim and blazer look has become sort of a tried and true, with the flexibility of dressing up (with a blouse and heels) or dressing down (a graphic tee and sneakers). Bloomingdale’s carries a wide array of fabulous investment blazers, from tweed to tailored, and at all price points. A buttery soft leather jacket can also be the perfect compliment to your 3-piece look.

Coats are another splurge-worthy category, and while we may live in Florida, there are some coats that are worth the investment, and a timeless travel companion. Enter the iconic Burberry trench coat that can be a part of your closet for years to come, as well as something to be passed on to the next generation. I have seen vintage Burberry trenches and they truly stand the test of time in style, quality and durability. 


Splurging on classic jewelry is rarely an unwise decision, as long as you invest in classic styles.  Go for gold or silver pieces, as these metals remain relevant season after season. When it comes to stones, diamonds are a girl’s best friend- and that’s because they retain their value! 

Classic statement pieces like gold bangles or hoops, diamond studs, tennis bracelets, etc will not only compliment every look, but will be an heirloom within the family that can stand the test of time. 

If you really want to go for the gusto with fashion jewelry, take a look at the classic Chanel brooch or strand of Chanel pearls, to wear with your blazer and jeans of course! These are luxury costume pieces that carry a seriously high price tag but can be worn day or night, and for years to come. 

If you are ready to begin upgrading your wardrobe, do your research and start slowly. Investing in your wardrobe is a process, not a race. Don’t feel pressured to get everything all at once. Consider going in person and working with a brand professional who can help guide you in the right direction, and give you that incredible luxury experience. The goal is to ensure you look good and feel good. Don’t forget, investing in your wardrobe is investing in yourself!