Shopping·14 min read

Stylish Gifts for Your Trendiest Friend

Design: theSkimm | Photos: Girlfriend Collective, Hill House Home
October 24, 2022

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You can always count on us to answer the tough questions, like what do you buy for someone who’s incredibly stylish and always on trend? Aka the person you go to for fashion advice, the next big look, and to ask if you should wear that shirt with those pants. So if buying them a gift leaves you and your fave Chelsea boots quaking, let us be that person for you now. (It’s also our job.)

We’ve found things that are sure to delight even the trendiest, most tapped-in person in your life, like an of-the-moment sneaker and an oversized leather bomber jacket. You may even be tempted to pick up a thing or two for yourself too. Go ahead, make them proud.Want more holiday gifting ideas? Check out The Shoppes at Skimm Ave. for our recs for everyone on your list.


An Ugg slipper worn by celebs like Megan Fox and Gigi Hadid…

Say no more. Help them achieve the perfect off-duty model look with these fuzzy slides that feature the classic Ugg plushness on the outside, and come in eleven colors (we’re partial to the hot pink). The platform of this slipper-sandal hybrid ensures they’re comfy enough to scuff around in while running errands or grocery shopping. Just add jeans and a white tee, and TMZ will be hot on their trail. ($37.50+, Nordstrom)

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ASTR The Label

A floral midi dress for literally any occasion…

We love love this dress. We’ve worn it to a wedding, bridal shower, on a date — you name it. It’s the fit that made us never want to let her go. It’s just the right midi length with a not-too-high slit to show a little leg. Plus, the cowl neck is endlessly flattering, and the straps are adjustable. It comes in eight gorgeous floral variations and sizes XS–XL. ($98, ASTR The Label)

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lively pajama set

An all-day lounge set that’s as comfy as it is chic…

Because if you didn’t post your self-care day on Insta, did it even happen? This insanely soft set is cozy enough to make you never want to leave your house. But trendy enough (hiiii, polka dots) to be seen by everyone. And with so much wide-legged, elastic-banded, front-pocketed goodness, we won’t blame you for snagging one for your bestie too. Especially since Skimm’rs can save big when they bundle. Trendsetters, unite. ($50, LIVELY)*

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A denim jacket that’ll never go out of style…

Gifting a timeless fashion piece is like preparing them for all the happy memories they’re about to create in this jacket. It comes in a nice light wash, has a classic fit that’s not too slim or cropped, and is made of cotton so it’ll get softer with each wear. It comes in sizes XXS–3X. ($118, J.Crew)

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A bomber jacket to pair with their athleisure ’fits…

It’s lightweight, breathable, packable, and looks more sleek and put-together than their favorite hoodie. We’d even pair it with jeans for a casual day at the office. Plus, it has a little stretch so it’ll be comfortable as they move from a workout class to running errands. ($44.99, Athleta)

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Dagne Dover

A fanny pack to stash their stuff…

Because long walks are in. This neoprene bag will keep their items secure while they strut their way to their favorite coffee shop. It has an interior pocket for a credit card, as well as a zippered pocket on the outside. It also has a key ring and a place to keep their lip balm (cute). Choose from one of six colors, and they’re ready to roll. ($95, Dagne Dover)

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A pair of sustainable sneakers for their morning runs…

Sustainability is always on trend. These are made with plant-based recycled materials that don’t skimp on comfort or cushioning. They have a bouncy feel and work well for long-distance running, if that’s their thing. They come in neutral colors but also several bright options. Life is short, get them the orange sneaker. ($160, Allbirds)

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A Chelsea boot they can turn into a cowboy boot…

Yes, you read that right. These suede Chelsea boots, with a cushioned sole and barely-there heel, can transform into another style in just one step. All they have to do is strap on the detachable western upper (that’s sold separately) and yeehaw — they’re ready to ride. How cool is that? ($345, Alterre)

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A super high-rise jean for all-day comfort…

If they’re abstaining from the low-rise pant trend (same), these sit above their belly button and will elongate their legs no matter their height. They’re made of organic cotton with a hint of stretch, so they won’t feel constricting when they sit down. They come in eight washes, two lengths, and sizes 23–35. ($98, Everlane)

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A headband to take their outfit to the next level…

Each of these headbands is handmade with a punch-needle technique and has a felt back for added comfort. No hair day will be a bad one when they slide this statement accessory on with a casual white T-shirt and jeans, or a dress for the office. It comes in a daisy or cherry print. S’cute. And for more great holiday gifts from Etsy, shop here. ($17.94, HoneyArtandNature via Etsy)

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Girlfriend Collective

A half-zip pullover that’s incredibly cozy…

Bless whoever invented the half-zip sweatshirt. Time and time again we find it’s the best light layer for everyday wear. This one is made of recycled micro-fleece for the softest sweatshirt they’ve ever owned. It has an oversized kangaroo pocket, a slightly cropped length, and an adjustable hem that can be cinched up when the wind is doing more than whispering. We love the baby blue, but it also comes in black and gray. Psst…use code SKIMM20 at checkout for 20% off (minimum purchase of $100). ($98, Girlfriend Collective)

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A bodysuit that will become their blazer’s new best friend…

Finding a good bodysuit to pair with jeans and a blazer is absolutely essential for a fashion-forward person. This one has a high neck, is made of recycled polyester with just the right amount of spandex, and has a full-coverage bottom. Aka it has every element to be their new wardrobe go-to. It also has removable bra cups, comes in three solid colors, and sizes XS–4XL. ($78, Frankly)

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Saks OFF 5TH

A shirt-jacket by an early-aughts brand…

Your stylish friend already knows, Juicy Couture is back in a big way, and they make much more than their classic velour tracksuits. Like this soft faux leather shacket (who couldn’t use a shacket?) that looks just as good layered over a white tee as it does over a dress for the office. It’s also perfectly oversized. Juicy, indeed. ($79.99, Saks OFF 5TH)

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New Balance

A New Balance sneaker cause all the cool kids are wearing NB…

It’s likely they already know that New Balance is undergoing a major revival. Impress them by being in-the-know and gifting them these vintage-inspired 574s. They come in red and navy colorways, and look great when paired with trousers for the office or a pair of leggings on the weekend. Plus, they’re super comfortable. They can thank you later. ($84.99, New Balance)

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A cowboy boot they’ll wear for years…

Okay, hear us out. We know these are pricey, but they’re an investment piece they’ll be grateful for. These midcalf beauties have a small heel, pointed toe, and contrast piping like traditional Western boots. They have a padded upper, so when they’re mounting their horse or, more likely, showing up to work with the coffee that made them late, they’ll still be comfy. We’re having a hard time choosing between the white, brown, or black. They’re that good. ($498, Reformation)

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A bomber jacket that looks way more expensive than it is…

The jacket of the moment is a leather bomber. When we saw this one, we couldn’t believe the price tag. The brown leather is soft and comes with an already worn-in look. Like they just pulled it out of their dad’s closet. Size up for an even roomier fit. ($102, Nordstrom)

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A trench for rainy, windy days…

Every capsule wardrobe needs a trench. They’ll find themselves grabbing this one for more than just blustery days, as it’s a great transitional weather piece too. It’s made of water-repellent cotton, has a belt to cinch the waist, and a notched collar. Pro tip: All the fashion girlies tie the belt in the back, but we’re betting they already knew that. ($119.99, Nordstrom)

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Hill House Home

A dress so comfortable, they’ll want to lounge in it…

The nap dress trend is still going strong. If they’re into the idea of dressing for their inner coastal grandma, gift them this variation of the original, but with added smocking at the bust, a ruffled hem, and midi length. This is slightly more Alice in Wonderland at the tea party, but we’re here for it. It comes in several different patterns and either wrinkle-resistant fabric (yes, please) or cotton. ($150, Hill House Home)

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A ring you can customize…

Because personalized jewelry is always a good idea. Engrave their name on this 14K-gold plated band. Or their nickname, a cute phrase, or the name of your shared favorite spot from the college days. The max is eight characters, so feel free to get a lil’ crazy. Plus, the block lettering is so chic. ($138, BaubleBar)

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Naked Cashmere

A cashmere sweater that always looks good tucked into jeans…

The boatneck style, the effortless slouchiness, the ribbed trim. Chef’s kiss. Choose from one of three neutral colors, and you can sleep peacefully at night knowing you’ve given them something they’ll never get tired of. It comes in sizes XS–L. ($135, Naked Cashmere)

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A pair of joggers they’ll never want to take off…

These are made of sustainable French terry that will retain its shape and never pill, no matter how fast they’re power-walking to get those errands done. The best part: They feel like walking around wearing a cloud. They’re that soft. There’s no harm in picking up a pair for yourself as well to see what all the fuss is about. ($98, Softwear)

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Saks OFF 5TH

A two-tone watch that goes with everything…

This stainless steel bracelet-watch is simple yet eye-catching. It has a round face with pretty Roman numerals. It’ll complement any of their existing everyday jewelry, so there’s no need to worry about whether they’re a gold or silver person. Bling, bling. ($75, Saks OFF 5TH)

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*This denotes a sponsored section.

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