11 Fashion Items Everyone In Their 20s Should Invest In

From core staples to the festive must-haves.

by Shelby Ying Hyde
Originally Published: 
Shelby Hyde
fashion investments in your 20s
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If your 30s and 40s are about enjoying the fruits of your labors, then your 20s are all about laying the groundwork. This line of thinking also applies to matters of your closet, which is why this list of fashion investments to make in your 20s is filled with highly practical — yet fun — essentials. In order to build a well-rounded wardrobe, one must start with a substantial foundation of core pieces that you feel confident in relying on and will, most of all, work hard in your wardrobe.

As someone in their mid to late 20s, the way I think about shopping has changed dramatically over time. In the last seven years, I’ve entered the workforce and started supporting myself, which meant more money to invest in my wardrobe. But even though I had the funds to shop, I didn’t focus so much on whether my purchases made sense in the long run. Now, with only a few years left until I enter my 30s, I’m beginning to notice the benefits of investing in those go-to staples early on and encourage all 20-somethings to begin doing the same.

“Starting to invest your wardrobe in your 20s is totally necessary,” New York-based stylist Bryant Simmons explains to TZR. “They are the years where you are still figuring out who you are, what you want to do, and who you want to be. A sharp jacket you bought at 23 might be the jacket that lands you your dream job at 28,” he adds.

However, Simmons’ suggestions came with a few stipulations that can take you from a savvy buy to a one-hit-wonder. Key points included only cashing out on the classics and pieces that are made with desirable fabrics, like cotton, linen, silk, and leather because you know it will last. “Leather ages with you and like wine gets better with time,” he explains. He adds the suggestion to invest in neutral colors and solids, as these pieces will be the backbone of your outfits. And if you’re still not sure where to begin, Simmons offers a list of timeless brands as a point of reference — whether for inspiration or purchase. “For those just starting out, I recommend starting with classics,” he says. “Brands I would suggest are YSL, Burberry, Levi’s, Everlane, Cartier, Gucci, APC, Rag & Bone, The Row, Prada, and Raey.”

Now with a better sense of what should be on your radar as you start taking stock of what you’re wardrobe’s missing, below is a comprehensive list of the items that should be on your itemized checklist to ensure you’re covering all your bases. Plus, a selection of shoppable styles to get you off in the right direction.

We only include products that have been independently selected by TZR’s editorial team. However, we may receive a portion of sales if you purchase a product through a link in this article.

Fashion Investment Pieces for Everyone In Their 20s: A Well-Tailored Suit

Between job interviews and events that call for more polished attire, a well-tailored suit is a must in every 20-something’s core lineup. While it may not get as much use as jeans, having the smart set in your arsenal will help you stay ready. It’s also worth noting that suit separates work just as well when worn by themselves as they do when styled together so it’s almost a guarantee that you get the most out of your investment.

Fashion Investment Pieces for Everyone In Their 20s: Trench Coat

A classic khaki trench coat is perfect for transitional seasons and unpredictable weather. On overcast days where a traditional puffer or overcoat would be too heavy, your trench will offer just the right amount of coverage, without taking away from the outfit as a whole. It will also come in handy during the fall when piling on the layers is a necessary occurrence. Try slipping yours over your favorite loungewear set as you ease back into “real clothes”.

Fashion Investment Pieces for Everyone In Their 20s: Timeless Everyday Bag

When it comes to investing in your wardrobe, skip the trendy silhouette for the day-to-day and stick with a style that will stand the test of time. Clean lines and neutral hues are a great place to start for those that are a bit stuck. It’s also worth doing a bit of research to be able to identify house codes and brand signatures that are meant to transcend season. A prime example, Coach reissued its archival “Tabby” bag in a plush, pillow silhouette that may have gone viral on TikTok, but it will also remain a tried-and-true classic long after the hype wears down.

Fashion Investment Pieces for Everyone In Their 20s: Bold Going-Out Bag

Every well-dressed person in their 20s needs a statement-making going out bag that will supersede their everyday carryall. Sized to fit only the essentials, the style should be embellished yet versatile enough that it can be worn multiple ways without looking too formal. You can’t go wrong with an art-inspired design or something covered in crystals to add an extra glam factor to even the most basic ensembles.

Fashion Investment Pieces for Everyone In Their 20s: Reliable Boots

In your 20s, there’s always an event to attend. And since you’re on-the-go, it’s important to have a pair of sturdy and reliable boots that are as chic as they are practical and functional. What’s even more important is that they will be able to withstand the wear and tear that comes with your stacked calendar. This is one of the reasons why splurging on a high-end pair made for durability will cause you less trouble down the line.

Fashion Investment Pieces for Everyone In Their 20s: Substantial Coat

If you only invest in one piece for your wardrobe, it should absolutely be a coat — even if you don’t live in a place where it gets cold. For those of us that experience all four seasons, finding a substantial piece of outerwear that’s fully lined and will keep you protected against harsh winds and flurries requires an investment. If you live on the West Coast, put your money towards moisture-wicking layers that will keep you dry (and warm) when the time comes.

Fashion Investment Pieces for Everyone In Their 20s: Undergarments

One of the first signs that you are bridging the gap into adulthood is that you’ve started to sift through your underwear drawer and upgrade to quality brands. Whether it’s seamless shapewear, nude hosiery, or everyday cotton undies, your undergarments should make you look and feel your best, at the same time. As you go through your 20s, think more about the little details and take appreciation for the purpose they serve in your wardrobe.

Fashion Investment Pieces for Everyone In Their 20s: Slip Dress

Slip dresses at any length are essential to the 20-something’s wardrobe; they transcend seasons and trends with ease, regardless of the cut you go with. Whether you end up wearing it to lounge around the house or dress it up with heels and a clutch for a late dinner out, the one-step look is an easy way to give others the impression that you put a lot of effort into your outfit without any of the stress.

Fashion Investment Pieces for Everyone In Their 20s: Menswear Shirt

An oversized menswear shirt is a versatile staple that’s often overlooked. If you want to smarten it up, just add a pair of tailored trousers with loafers and stacks of gold jewelry. However, it can be dressed down too when layered over a cropped top with boxer-style shorts and sneakers when off-duty. Pro tip: Pull a full on Carrie Bradshaw and go a size up to wear it sans pants.

Fashion Investment Pieces for Everyone In Their 20s: Black Oversized Blazer

Even if you have a two-piece black suit, it’s important to have an oversized dinner blazer at your disposal, too. In most instances where the full set may not be necessary, opting for your oversized style with more relaxed pairings is an instant hit. Famous accompaniments include (but are not limited to) boyfriend jeans, biker shorts, or even your go-to slip dress. The bottom line is that it serves a completely different purpose in your closet than the well-tailored set and should be treated as such.

Fashion Investment Pieces for Everyone In Their 20s: High-Rise Denim

If you choose the right denim, it only gets better as time goes by. So if you invest in a few pairs of high-rise jeans in your 20s, by the time you’re in your 30s and 40s, they’ve already been molded to that perfect fit. Plus, as you begin to start safely going out, they’re bound to become one of your most worn pieces of clothing, so they’re worth investing in.

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