1
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.
2
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.
3
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).
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4
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).
5
A Basic Coat
Lauren Ralph Lauren Double Breasted Wool Blend Coat
A winter coat is essential no matter your aesthetic (unless you live in a warm weather climate). There’s something so easy about the ever-flattering double-breasted coat—it’s genderless and basic in the best way possible. Our tip for finding the best one? Look at the fabrication first and foremost. When winter rolls around, wool is king.
Honorable mentions: Max Mara for those looking to spurge on the very, very best. For wallet-friendly outerwear, & Other Stories makes great silhouettes that toe the line between classic and modern.
6
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.
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7
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.
8
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.
9
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).
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10
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.
11
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.
12
Flattering Jeans
Good American Good Legs High Waist Crop Skinny Jeans
Now 50% Off
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This might feel like an endless search, but when you find your perfect pair of jeans, you just know. This can vary from straight legs to skinny, but owning denim that complements your assets is an instant mood-booster. Good American makes great mid-range denim.
Honorable mentions: AGOLDE is a gold standard for those looking for that perfect, straight leg style that isn’t a mom jean (Levi’s Wedgie fit also deserves a call out). For skinny styles, try Frame’s popular Le High ($190) style or surprise, surprise, another Levi’s style that boasts over 60,000 reviews on Amazon.
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13
Leggings
Alo Yoga 7/8 High-Waist Airbrush Legging
Now 40% Off
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Here’s another pandemic-influenced pick: chic leggings. We live in these now, so owning a good pair might just make you want to work out. The best part about Alo Yoga’s leggings is not only the quality, but the color range and matching sets.
Honorable mentions: Beyond Yoga’s spacedye leggings for a pair that feels like a second skin. TikTok’s viral leggings do work, just FYI. For more options, check out our roundup here.
14
A White Tee
Uniqlo U Crew Neck Shirt
15
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.
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16
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.
17
"Comfortable" Formal Shoes
Stuart Weitzman Nudistsong High-Heel Sandals
These are the heels you bust out for every special event, because you know you can stand in them all night long. Just listen to your feet and stick to a style that you’re comfortable in, be it a stiletto or a block heel. Stuart Weitzman’s Nudistong heels are a celeb-favorite for a reason.
Honorable mentions: Salone Monet has a cult following for its inclusive color range, so you can find your true nude shade.
18
Simple Ankle Boots
Brother Vellies Empire Platform Boot
Whether you’re team brown leather or team black leather, a simple ankle boot is a year-round essential (yes, we sometimes wear ankle boots in the summer too).
Honorable mentions: By Far boots veer toward less classic, and are a fave brand amongst the Bella Hadid types. Khaite makes industry-loved boots that come with a high-fashion price tag. For a high street budget that doesn’t skimp on quality, look to COS, Free People, and trusty Dr. Martens.
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19
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.
20
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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