Upper East Side Grandmothers Are the Vision—25 Items to Buy

“Old money,” “steal wealth,” and “quiet luxury” are all buzzwords floating around right now. People are looking for a way to tap into these aesthetics, but many of them are looking right past the women who have already been doing it for decades: Upper East Side grandmothers. On a few recent scrolls through TikTok, I’ve noticed that this aesthetic is getting a lot of love, with fashion people piling on intentionally gaudy jewelry, oversize faux-fur coats, tweed jackets, and anything J.Crew.

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32 Rich-Looking Items That I’m Obsessed With for Winter

One thing about me, I’m going to dress like I’m way richer than I actually am. I like to think I have a special knack for finding items that can magically transport me to a different tax bracket. Because after all, it’s about dressing for the life you want, right? This winter, I am taking my love for rich-looking items seriously and plunging headfirst into one of TikTok’s favorite aesthetics, the “rich mom” aesthetic. Think casual yet chic cashmere sweater, elevated takes on jeans, ballet flats, and Mary Janes galore. I was looking for a few new picks to add to my winter wardrobe and found 32 pieces that were too good to pass up.

Keep scrolling to take a pick at the rich-mom shopping list curated by yours truly.

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6 Simple Outfit Ideas for When You Don’t Know What to Wear

Effortless elegance is my fashion goal when it comes to everyday dressing these days—outfits that make me feel polished and put-together but require very little effort. Let’s be honest. When it’s cold and gray out, I’m not always feeling very inspired to assemble anything extraordinary. Instead, I like to rely on a handful of simple yet stylish tried-and-true outfit combinations that I can put together easily and will make me look 10 times chicer.

If you, too, need some inspiration this winter, are stuck in a sweatpant rut, or just need some easy looks that ooze elegance, then take a look below. I’ve scrolled through some of our favorite fashion accounts and selected six simple outfits that are super easy to put together. With just two or three pieces max, you can quickly achieve a chic and cohesive look—zero effort required. You’re welcome.

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This Chic Accessory Will Make Your Jeans Feel So 2024

Sometimes, the simplest styling tricks can elevate an entire outfit. As editors, it’s pretty clear to the Who What Wear team that small additions like sleek belts and red socks truly make an outfit. Case in point, our editors’ new favorite winter-approved outfit hack: tights with jeans. 

The layered combination isn’t new by any means throughout the colder months, but lately, we’ve been seeing brands, influencers, and other editors wear their favorite tried-and-true jeans with a pair of unexpected tights for a fun peekaboo moment. Whether you’re opting to layer red tights under jeans or fishnets with your go-to pair of slouchy denim, this subtle, It girl–approved trend is the easiest way to make your winter jeans outfit feel 10 times fresher. 

Below, scroll on to discover some chic tights-with-jeans outfit ideas and shop all of our essentials to get the outfit.

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The 12 Best Snow Boots for Winter, Per This Arctic Resident

As an editor who isn’t adjusted to winter dressing by any means, I have to admit that I panic at the sight of snowfall. Admittedly, I still haven’t bought any true winter boots given the lack of any severe winters in New York City. Most of the time, my chic (but dangerous) studded ballet flats will be fine, but given the amount of snow New Yorkers are expecting in the coming weeks and days, my on-trend footwear isn’t going to cut it.

Instead of combing TikTok for hours for video footage on how to buy the best snow boots, I went straight to the source. Yep, Arctic Circle influencers. After a deep dive through my hyper-niche algorithm, I reached out to Thea Selven, or @svalbardthea on TikTok. As her username suggests, Selven lives on Svalbard. Svalbard is a small, rugged island situated between Norway and the North Pole, making it one of the northernmost inhabited places in the world. Naturally, I knew her advice on getting the best snow boots was invaluable.

“In winter, we can have degrees below -30° Celsius! So it’s all about keeping warm and functional, not so much about what’s trendy and not,” Selven explained. It’s a lesson I can learn as a fickle fashion editor—sometimes, function outweighs fashion!

Below, read Selven’s hidden secrets for buying the best snow boots, and scroll on to discover a few chic pairs worth adding to your cart before more snow falls.



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How to Style a Puffer Jacket, According to a Celeb Stylist

Puffer jackets and chic styling don’t often go together at first glance. How to style a puffer jacket isn’t top of mind for most people. Instead, winter dressing is usually about making sure that you’re mentally and emotionally ready to step out of the door without regretting not putting on that extra layer of clothing.

As a new-ish New Yorker who has never experienced a true winter in her entire life, I have to admit that I’m in the latter camp. So when it came to finding a winter jacket that both looked and felt good, I knew I had my work cut out for me—until I asked Karla Welch, that is.

Welch, who has years of experience styling top A-List clientele like Hailey Bieber, Tracee Ellis Ross, America Ferrera, Karlie Kloss, and Lorde, among others, partnered with Canada Goose this fall and winter to make puffer jacket outfits feel more like a creative choice rather than a chore. 

“We really wanted to show how a warm functional coat can add to a look and become part of the entire fit vs. just something you wear to stay warm and dry,” Welch, who partnered with the legacy outwear brand in styling its fall/winter 2023 drop, explained. “This new collection is super flattering on the wearer and the color offerings are in arrays of muted tones with pastels here and there, that can easily work themselves into any wardrobe and on any type of person.”

She’s not wrong—a quick glance at the in-season offerings drastically shows that this isn’t your father’s bulky all-black winter puffer of the past. Earth tones and soft, muted mattes instantly elevate the collection, with a minimalist take on quilting, logos, and hardware from the Canada Goose design team.

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25 Chic Finds From J.Crew’s The Long Weekend Sale

Oh, you thought you could take a break from sale shopping just because Cyber Month ended? Same. Then I stumbled across J.Crew‘s latest, appealing 40%-off sale that’s only running until 11:59 p.m. EST on January 16, leaving me with no choice but to drop everything and look for deals before it’s too late and everything sells out. We can’t have that, can we?

I spent the last hour scrolling through this sale’s offering, hand-selecting the best deals and adding pieces into my cart that I simply have to bring into my 2024 rotation, from denim jackets to satin camisoles to “dripping in wealth” outerwear. Now, it’s your turn. Trust me—this is one sale you won’t regret spending time (and money) on.

(PS: There is another sale happening with up to an extra 70% off select items when you use code SHOPSALE. Discounted prices reflected below.)

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14 of the Best Cozy Sweaters to Wear All Winter

Fashion expert Alexa Chung showcased her coziest sweater on Instagram lately, and ever since, I’ve been keeping a mental list of the best styles I’ve come across, both online and on a couple of recent trips to Oxford Street. Of course, knitwear is hitting the stores thick and fast now that the clocks have gone back and the temperature has dropped significantly. Everyone from H&M to COS has some gorgeous styles I just want to wrap myself up in, and no doubt, you will too. 

Keep scrolling to see my edit of the 14 best cozy jumpers out there right now, from alpaca-blend to cashmere polo necks. They’re all ready to be your new best friend this winter. 

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5 Winter Fashion Trends That Are Ageless

There is a 28-year age difference between my mother and me. (I’m 35, and she’s 63.) Despite the age difference, we tend to gravitate toward similar items because our aesthetics often mirror each other. Although, this probably isn’t so shocking given that age has nothing to do with what you should or shouldn’t wear. I should also note that cold weather is my favorite. While my mom really loves summer, she adores winter from a sartorial standpoint. And yep, there are actually five trends for this season that we’re both loving.

Below, you’ll uncover the still-relevant in 2024 trends that actually started in 2023, and will still be essential for the months of cold weather ahead. You’ll notice everything from the color of the moment to a few trends that are highly wearable and could be styled in a multitude of ways.

Keep scrolling to check out the winter trends that get a yes from us, including visual inspiration for each from various fashion people.

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5 of the Best Narrow-Calf Boot Brands You Need to Know About

It’s boot season, and that means you have every right to scoop up the best boots to replenish your shoe closet. But if you typically tend to struggle to find narrow-calf boot brands for your smaller calves, trust us when we say you’ve come to the right place. There are tons of brands out there that make boots with smaller, narrower calves in mind, and a few brands always hit it out of the park. After doing tons of market research, looking into product reviews, and, of course, wearing these brands ourselves, we’ve been able to compile a list of five of the absolute best narrow-calf boot brands we just know you’ll love. Across the board, each of these five brands is known for making lots of styles specifically catered to narrow-calf people, or some of these styles simply feature a tighter fit. No gapping here!  We know that investing in a good pair of boots might seem like a daunting task, but with a little help from us, your fashion besties, we think you’re going to love not only the brands on this list but also the narrow-calf boots we’ve found. Read on to see and shop our edit, along with the top customer review for each boot style, sizes and colors available, why we think they’re great options, and so much more.

Frye is a brand all fashion people know and love. Known for its craftsmanship and attention to details and trends, its shoes, and especially its boots, always tend to sell out quickly. This American-made company started back in 1863 and has since grown to be one of the best boot brands in the world, not only because of the beautiful and timeless styles but also because they cater to those with both narrow and wide calves. Frye boots tend to go anywhere from $300 to $500 depending on the style, but each boot is crafted with premium leather—so just keep that in mind!

This timeless style comes in multiple colorways and can be styled with anything from skirts to dresses, leggings, jeans, and more. Size Range: 5.5-11. Colors Available: Dark Brown, Saddle, Banana. Materials: Leather. Customer Review: “Beautiful leather boots! Even more comfortable than I had expected! These exceeded my expectations, and I cannot wait to have these as a staple in my wardrobe.”

Cowboy boots aren’t meant to be too tight around the calf area, and if you have narrow calves, you’ll love the way they perfectly rest against your legs. Size Range: 5.5-12. Colors Available: Dark Pewter, Black, Ivory, Brown, Black Tooled, Chocolate. Materials: Leather. Customer Review: “Gorgeous and fit well! Very well made!”

The button details on these boots are simply perfect, and with an easy pull-on nature, these will easily come off and on for those with narrow calves. Size Range: 5.5-12. Colors Available: Whiskey, Mahogany, Cognac, Black, Grey, Redwood. Materials: Leather. Customer Review: “I’ve been wanting these for years and finally got them! They are beautiful and comfortable- perfect if you have narrow feet and thin legs. I love them!!”

There’s nothing we don’t love about these tall boots. And while we’re fans of the caramel hue, they also offer a lot of other color options for every aesthetic. Size Range: 5.5-12. Colors Available: Caramel, Black, Black Brush Off, Redwood, Antiqued Black, Dark Brown. Materials: Leather. Customer Review: “I have slender legs and these boots fit me perfectly – thank you for making great quality leather products.”

If you’ve been to a luxury shopping mall or scrolled through your favorite influencers’ social media feeds, chances are you’re already familiar with designer Stuart Weitzman. This brand began in 1986 and is known for its sexy styles, stunning silhouettes, and sturdy designs. Additionally, its boots are available in multiple width options, typically including narrow, medium, wide, and even extra wide. With a higher price point (from around $600 to $2000), these shoes are definitely an investment, but we think they’re well worth the splurge.

Stretch booties are the perfect style for those with narrow calves because they will hug your feet in all the right places! We’re obsessed with this specific pair from Stuart Weitzman. Size Range: 3.5-13. Colors Available: Black, Taupe. Materials: Leather. Customer Review: “These booties are made with high-quality leather. They are stretchy around the ankle which I love because of this you can wear them with a dress or skirt. My favorite thing to wear these booties with is boot-cut jeans. It gives them an elevated look.”

For a classic black bootie, you can’t go wrong with this simple style that will remain in your closet for years to come. Size Range: 3.5-13. Colors Available: Black. Materials: Leather. Customer Review: “Love these Chelsea boots. Perfect height. Beautifully made and super comfortable. Very happy with my purchase.”

If you’re on the hunt for an over-the-knee boot that fits your narrow calves, look no further than this beautiful option our editors are in love with. Size Range: 3.5-13. Colors Available: Black. Materials: Leather. Customer Review: “Oh my goodness, I feel so confident and beautiful wearing these. Elevates every single outfit and the best-fitting boots in the world.”

Whether you’re into a grungy look or just want a style that gives a bit more edge, go for this fun style that’s available for people with narrow feet. Size Range: 3.5-13. Colors Available: Black, Oat. Materials: Leather. Customer Review: “I was introduced to Stuart Weitzman shoes in the mid 1980’s. They are the best shoes I have ever seen and worn.”

Founded in 1928, Cole Haan has been a pioneer in the shoe industry for both men and women. With luxe designs and special attention to leather, we love looking to this brand for narrow calf boot options. From traditional riding boots to ankle booties and even combat boots, there’s a style available for anyone. The typical price range is $90 to $250.

A classic style that you can wear for years to come, the Noelle Boot from Cole Haan deserves a spot in your shoe closet. Size Range: 5-11. Colors Available: Black, Chestnut, Tornado. Materials: Leather. Customer Review: “Excellent quality and good fit. I just love them!”

With a slightly square toe and a narrower upper portion, this boot will look amazing with an assortment of outfits. Size Range: 5-11. Colors Available: Black, Irish Coffee. Materials: Leather. Customer Review: “Very flattering booties. I have long, narrow feet and these worked well.”

Riding boots are such a versatile style that can go with all sorts of aesthetics, and we love how this boot is both timeless and trendy at the same time. Size Range: 5-11. Colors Available: Black, Black Woven, British Tan. Materials: Leather. Customer Review: “These boots are beyond expectations!!! The fit, the leather, and the quality are exceptional.”

Combat boots are another boot style everyone knows and loves, and these specific ones are our current faves for those with narrow calves. Size Range: 5-11. Colors Available: Black. Materials: Leather. Customer Review: “Great boots! Comfortable and high quality.”

Established in 2005, Marc Fisher is a shoe brand fashion people need to know about. With fair prices and a wide assortment of sizes to choose from, those with narrow calves will find that there are plenty of boot styles. We especially love this narrow-calf boot brand because of the classic silhouettes that will never go out of style. As far as pricing goes for boots, most are in the $170-to-$300 range.

Our fashion editors have been loving the biker boot trend, and these nice-fitting boots from Marc Fisher just might be some of the best the market has to offer. Size Range: 5-11. Colors Available: Dark Natural, Black. Materials: Leather. Customer Review: “Great boots. Nice fit. True to size.”

We love a slouchy boot moment, and these comfortable ones from Marc Fisher would look stunning any time of year. Size Range: 5-11. Colors Available: Dark Red, Taupe, Black Leather, Black Suede. Materials: Leather. Customer Review: “Comfortable.”

The block heel is what initially sold us on these knee-highs, but honestly, the entire boot is pure perfection. And if you have narrow calves, you won’t be dealing with any gapping or feel like you’re swimming in them. Size Range: 5-11. Colors Available: Black, Medium Natural 102, Medium Natural 103, Medium Natural 104. Materials: Leather. Customer Review: “Super soft and comfortable boots! Fit perfectly and the heel height makes me feel I can wear it all day with no pressure. Definitely, it will be my first choice of this winter in my closet.”

We’re willing to bet that everyone (and we mean everyone) is familiar with Steve Madden. With a revolutionary take on shoes, this is a brand that’s approachable and offered at various price points (typically $100 to $250). Getting its start in 1990, Steve Madden has since completely taken off and is now one of the leading brands in the shoe industry—with some of our absolute favorite narrow boots to shop!

Coastal cowboys will adore these cowboy boots from Steve Madden. We’ve personally worn these and can attest that they’re not too wide. Size Range: 5.5-11. Colors Available: Black Mult, Chsnut Sue, Bone Leather, Green Leather. Materials: Leather. Customer Review: “The most comfortable boots ever. The inside feels so amazingly soft. Very sexy and elegant, especially the bone color. I’m purchasing another color for sure. Maybe the black or maybe the brown, I’m not sure. I love them all.”

A classic leather knee-high boot is a necessity for any fashion person. This style from Steve Madden features a pointed toe and slim upper portion that’s made with narrow calves in mind. Size Range: 5.5-11. Colors Available: Black Leather, Black Crocodile, Oatmeal Suede. Materials: Leather. Customer Review: “These are the perfect boot. I have never been a fan of kitten heel until this pair. So comfortable. For dressing up or down. I love to pair them with a skirt & tights! You won’t regret these!”

A platform boot with moto edge? Sign us up. If you have narrow calves, you’ll especially love the way these rest. Size Range: 5-11. Colors Available: Black. Materials: Faux Leather. Customer Review: “I have scrawny legs and ankles. 5’2. They hit right below my knee and don’t slouch. No gap and wasn’t tight. Very comfortable too.”

This mid-calf boot is perfect for those who have more of a narrow footing and calf, and we simply adore the colors on offer—especially the tan suede option! Size Range: 5.5-11. Colors Available: Tan Suede, Black Leather, Chestnut Suede, Bone Leather. Materials: Leather. Customer Review: “Love them! Comfortable and stylish.”

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