1
A Tailored Trouser
Wilfred High-Waisted Wide-Leg Trouser
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Even if you don’t work in an office, black slacks are considered casual. I wear this exact pair with everything from going-out tops to oxford shirts and band tees.
Honorable mentions: Fashion editors love to scour secondhand sites for Old Celine trousers. For designer trousers, The Row is a tried-and-true. J.Crew’s options are also great if you prefer a slimmer cut.
2
A Black Crossbody
Chanel Small Classic Handbag
Do I really need to convince you to own a black bag? Probably not. A Chanel classic flap is the ultimate investment (they hold value extremely well on the resale market), but you don’t need to throw down this much money to get the same effect in your life. We highly recommend considering the below styles, too.
Honorable mentions: Madewell’s crossbodies are sturdy, affordable, classic, and will reel in compliments as easily as a Chanel will (true story). Some more brands affordable we love for a simple crossbody: Brandon Blackwell, JW Pei, and don’t forget about buying a used designer handbag.
3
A Leather Belt
UnFader Faux Leather Belts with Double O-Ring Buckle
A belt truly pulls an outfit together. Those are the rules!
Honorable mentions: Frame belts are a hidden gem. They’re pricey, but we doubt you’ll ever need to buy one again.
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4
A Wear-Everywhere Dress
Realisation Par The Teale
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This is not your special occasion dress. Rather, this is the frock you throw on too often, without care, because it’s what you feel your best in. It’s old reliable for days when you don’t know what to wear.
Honorable mentions: Hanifa for the bold, COS for the minimalist.
5
A Little Black Dress
Zara Draped Side Mini
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Ah, the LBD. It’s pretty much the ultimate wardrobe staple. The only thing that’s up in the air? The definition of the word “little.” The just-right length is in the eye of the beholder.
Honorable mentions: Are You Am I is an influencer favorite (but has limited sizing). ASOS is a great one-stop shop for LBDs in range of sizes and styles, but opt for one that isn’t of the single-use variety.
6
A Tote Bag
Telfar Large Oxblood Shopping Bag
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Carrying around NYC merch or an A24 tote bag is a flex, but do yourself a favor and invest in a non-canvas style that doesn’t break down or get super dirty. Hands down, Telfar is the number one pick.
Honorable mentions: Cuyana’s heavy-duty leather totes will last through an apocalypse. Yvonne Koné’s chic styles are made in Denmark, but with the Ivory Coast in mind.
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7
Hoop Earrings
Jennifer Fisher Mini Samira Hoops
Now 46% Off
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What’s not to love about basic hoop earrings? Celebs like Selena Gomez and Rihanna love Jennifer Fisher’s bold styles, but you can opt for thin hoops if you seldom take them off.
Honorable mentions: Mejuri, hands down, makes some of the best jewelry around, and it just happens to be super affordable. Win-win.
8
A Leather Jacket
ACNE STUDIOS Mock Core Leather Moto Jacket
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Very few aren’t into the moto leather jacket. It transcends trends and style preferences, fitting neatly into a hardcore punk look as easy as it does for someone who engages in Taylor Swift fan fiction.
Honorable mentions: All Saints Balfern Jacket ($489) consistently has rave reviews. Stand Studio makes great vegan options.
9
A Denim Jacket
everlane The Modern Jean Jacket
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Like I said, I’ll be the first to admit that not all “wardrobe classics” are for everyone. Despite not owning a jean jacket, I’m keenly aware that it’s the kind of item you should envision yourself throwing over anything, be it a spring dress or a Texas tux. This Everlane style is made with sustainable and eco-friendly practices in mind.
Honorable mentions: Levi’s is the OG. If you can’t skip a designer dud, go for Balenciaga. You deserve it.
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10
A Clean Hoodie
Tier Iced Mango Hoodie
If the pandemic taught us anything style-wise, having a nice hoodie is a new addition to the essentials list. This is not the one you wear while Netflix asks you if you’re still watching. Think of it as an elevated sweatshirt that you wouldn’t mind wearing to a restaurant.
Honorable mentions: Champion if you want that retro look (i.e. something that might mistake you for a Gen Z-er). Aritzia’s shrunken hoodie ($70) is my personal favorite. Pangaia makes stylish and ethical sweats.
11
A Transitional Sweater
H&M Sweater
Now 43% Off
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The actual style of this sweater is dependent on you, but owning one that is equally cozy enough for both brunch and lounging at home is important. I own two of these H&M sweaters and constantly get compliments on them.
Honorable mentions: With its high-quality cashmere and semi-psychedelic takes, The Elder Statesman’s knits are a fashion insider favorite, but come with hefty price tags. Alternatively, Victor Glemaud makes knitwear that both you and your mom will like (a true feat).
12
An Easy Slip Dress
Fenoel Sundance Slip Dress
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A slip dress is the kind of item that you think is a lot, but you end up wearing 24/7. Choose a color or print that speaks to your daily wardrobe.
Honorable mentions: I’ve lost track of how many of Silk Laundry ’90s dresses ($265) I own.
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13
An Oxford Shirt
Gap Oxford Perfect Shirt
Now 30% Off
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Think of an oxford shirt like a lightweight cardigan. You can wear it to the beach, to work, and over a slip dress.
Honorable mentions: Alex Mill ($125) makes a solid silhouette. For a heftier weight, try L.L. Bean’s affordable styles (I prefer the men’s styles, which are cut a little wider).
14
Basic Flats
Mansur Gavriel Square Toe Ballerina
A flat shoe that isn’t a sneaker or a sandal comes in handy when you’re running into the office unexpectedly. If you’re opposed to the ballet flat, we are a little obsessed with loafers.
Honorable mentions: H&M can be a great option for those looking to spend less, but these styles aren’t likely to last a lifetime.
15
White Sneakers
VEJA Espalar Sneaker
A pair of white sneakers hits different. Whether you like them a little scuffed or freshly buffed, they go with just about anything in your closet. Vejas in particular are sustainably made and endlessly loved by Meghan Markle.
Honorable mentions: Nike, of course, no matter the style.
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16
Shoes for Errands
Birkenstock Arizona Split Birkenstock Sandals
Now 55% Off
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You can choose to go minimal or weird with this wardrobe suggestion. These shoes are the ones you run around town in without a care in the world.
Honorable mentions: What can we say, Crocs are having a moment that doesn’t seem to be ending anytime soon.
17
Special Occasion Jewelry
Mateo 14kt Gold Pearl Curve Form Earrings
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Jewelry on a night out transforms not only your outfit, but your mood. Maybe it’s a necklace that you inherited from your grandma or a pair of earrings you invested in, but consider this something that puts a smile on your face every single time you wear it.
Honorable mentions: Irene Neuwirth’s beautifully carved stones are future heirlooms. The Last Line makes playful fine jewelry accessible. BaubleBar’s line of demi-fine styles is also a great alternative.
18
Everyday Jewels
Cartier Love Bracelet
You have jewelry you swap in once a year, and then you have jewelry that you forget to take off. Cartier’s Love bracelet is a steep investment, but it’s literally screwed onto your wrist, rendering its price-per-wear more than worth it.
Honorable mentions: Mejuri, again, deserves a shout-out. We also love basics from Oma the Label, ByChari, and Tiffany & Co. (if you can swing the latter).
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19
Face-Framing Sunglasses
Celine Cat Eye S193 Sunglasses
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I will reach for a pair of basic sunglasses over on-trend styles 95 percent of the time. Find a classic frame you love, and you won’t regret it.
Honorable mentions: Celine sunglasses are known for being the investment pair amongst fashion editors, but you really can’t go wrong with Ray-Ban. Meanwhile, Le Specs and Aperçu are both Insta-friendly brands that keep getting better and better.
20
A Flattering Swimsuit
JADE Swim Evolve One-Shoulder One-Piece Swimsuit
Now 60% Off
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Having a timeless bathing suit alongside your arsenal of wilder styles is essential for making you feel comfortable at the beach or pool. We deeply appreciate Jade Swim, because all of its styles strike the perfect balance between modern and classic.
Honorable mentions: Solid & Striped and Everlane for classic maillot silhouettes.
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