Imagine: the year is 2007, we’re in a major metropolitan area (US or otherwise). You’re an office professional and you’re also a woman. Monday, 6:30 am. An alarm clock goes off. Coffee, shower, outfit, toast with jam, makeup, brush teeth, leave for work—in that order. After the shower you check the newspaper for a weather report—clearish skies, low 50s as the high, high 20s as the low. Outfit. Outfit. What’s outfit again…

In 2007, I used to spend my time imagining myself as an at least 20-something professional. I lived and worked among the adults instead of enjoying recess with my fellow nine year olds. The fictional adult self I pictured myself as in 2007 was tall, like 6 feet in flats. She still wore the same little rectangle glasses as my child self does, but as a grown-up they are Chanel. She could wear heels without foot pain. She required what I used to call a “big girl bag,” aka she had enough stuff to fill out a medium-sized leather designer handbag. She could also fill out a bra underneath a work blouse or dress or whatever cool thing she’d be wearing. She had dilemmas like wondering how in the hell she’s supposed to dress for a 20-something degree Fahrenheit weather range as a 20-something year old woman. “Transitional,” as they used to say in the magazines to describe clothes that could go from day to night, from high temperatures to low.

“Transitional” is a resonant word to me as a 26 year old, what some might call a transitional age. Now officially on the other side of my 20s (when I celebrated my birthday last month, a former date 15 years my senior pointed out via Instagram DM described me as “26 going on 62”), I think I get the 2007 flavor of transitional dressing. It’s a smart midweight jacket with a thick cashmere sweater and a t-shirt underneath. It’s wool tights and a funky skirt on bottom, or trousers with thigh high socks for warmth. It’s a loafer, not a brogue. If you’re a heel wearer, it’s a polite block silhouette in a zany color or a somewhat suggestive stiletto in a shiny patent. It’s a big leather tote that can fit the jacket should you need to strip off a layer.

When getting dressed for work as an actual adult in 2024, I frequently recall to my imagined future self from 2007, a gal with an important job requiring a rigid yet unspoken office dress code, despite the fact that I work at an independent fashion magazine and can wear wool underwear as pants if I so choose. I share the same age as my fantasy self, but I am not 6 feet tall. Rather than little Chanel glasses (I tried this once, but got my swag jacked so hard I left it to the birds), I wear little blue Balenciaga frames, or sometimes my purposefully geeky Celine Coke-bottle tortoiseshell glasses when I want to be funny. I can fill out both a bra and a big girl bag, but can’t wear heels due to joint pain. I understand how to dress for the weather, but still can’t dress for the weather. The transition to the other side of my 20s has taught me that transitional dressing isn’t what it used to be.

Today, transitional dressing contains multitudes: transitional weather, day-to-night occasions, as well as a new notion of the hybrid or multiuse garment, like a hat that turns into a purse. A fashion dohickey, if you will. In 2007, transitional clothing meant layerable items suited for the many weather and formality-level changes that the typical person on the go needs for an eight-hour work day plus afterwork frivolities. In 2024, transitional clothing doesn’t need to remain appropriate between the office and the club, but from remote Zoom meetings to (maybe) leaving your house for the first time at 7:30 pm. We used to need transitional clothing to cover a lot of ground and occasions, but as we’ve started to work from home more post-pandemic, our clothing has standardized to the point where the traditionally transitional (say that five times fast) way of dressing doesn’t apply anymore. Instead, transitional dress still means multi-occasion wear with the added definition of modular accessories. Rather than the perfect leather jacket to transition seamlessly from office to party, we have an abundance of laptop-sized bags with a million and one compartments for digital nomads who work from anywhere (meaning from coffee shops or friend’s houses, globally) and matching “separates” (don’t get it twisted, these coordinating sets are ostensibly sweatpants) that can be formalized with funky footwear and the right jacket. This 2020s-specific idea of transitional dress as multi-use fashion products joins the tasteful layering and day-to-night leather jacket of 2007-transitional dress as an entirely new definition for the word in the fashion dictionary.

For this impending holiday season, I’ve compiled a list of brands with transitional products that add an edge to this upgraded definition of transitional clothing, including frilly pajamas that double as chic two-piece sets or home goods that can become warm accessories.

DAMSON MADDER

PERFECT BRAND FOR: your friend who’s always running late, your post-coquette friend who unironically loves bows, your friend who hates thinking about getting ready in the morning yet loves being pretty

If you’re a girl who wears clothes in New York, I bet you five American dollars that you’ve seen Damson Madder’s funky ads on Instagram Reels. After bodying the more depressing ills of the fashion industry (unsustainable practices and crazy fast overproduction, namely) from previous jobs, designer Emma Hill decided to go her own way and start her own brand during lockdown. “The brand really started with the intention to champion quality garments, made from responsible fabrications, but that were exciting and versatile to wear,” says Hill. After two hero styles, the Tilly Gilet and Leopard Cargo Jeans, had a viral moment online, Damson Madder took off.

For its AW23 collection, Damson Madder released a nightwear collection that immediately became a staple category for the brand. I first encountered these pajamas via an Instagram Reel for the brand showing a stressed Hill waking up late for work in her Maria PJ set, brushing her teeth, smoothing her hair, slipping into flats, and chucking a long trench over her sleepwear to head into the office. I pressed my thumb into my phone screen because, pause: those pajamas look like normal clothes! Not transitional between day to night, but night to day. “We have a lot of fun designing our nightwear collections, applying the most playful elements of our design handwriting as a brand like bows, oversized collars, and statement prints to nightwear,” continues Hill.

This season, the Antonella and Barbara PJ sets are reimagined in red tartan and leopard, as well as a blue stripe and rich cocoa brown with pale pink trim. You can purchase them here.

VISO PROJECT

PERFECT BRAND FOR: your friend who works from home, the design and home decor aficionado in your life, anyone who prioritizes being comfortable, anemics or anyone who runs cold

We’ve seen the bulky mohair sweaters from Marni, but have you ever seen the same swag, just translated into a blanket? Look no further than VISO PROJECT, a lifestyle brand started by David Vivirido and Francesco Sourigues after their 15-year-long careers in luxury brand consulting and publishing. “We started the brand while we were both still living in Barcelona,” says Vivirido. “At the time, we had opened a small art gallery and bookshop, selling a variety of magazines, photography, and illustrations. We began to wonder, what about unique home or design items? Everything on the market seemed either generic or outdated and that was essentially how VISO got started.”

Ranging from seasonally colored porcelain wares to blankets and throws in sumptuous cashmeres and mohairs, VISO PROJECT’s product line transitions from serious grown-up houseware to cheeky conversational pieces. Hypothetical scenario: You attend your Design Friend’s brownstone for a dinner party. After setting your keys and things down on a rare Lazzoni-manufactured catchall table, you’re welcomed to a rare knotted oak table where crunchy-looking hors d’oeuvres await on a white porcelain plate trimmed with navy crescent moons. Halfway through the appetizer, a centaur carrying a bow and arrow is revealed on the plate’s center; the person next to you has a long-haired figure holding scales on theirs. You’re a Sagittarius, your tablemate is a Libra. Design Friend winks at you as if to say, “Yes, I thought of that.” Everyone laughs, but the joke is one of taste, not hardy-har bar humor.

Another hypothetical, still from Design Friend’s house: You and your fellow guests have finished dinner, lounging in a bespoke conversation pit consisting of equally rare and equally Italian furniture to the entryway table with wine and expensive chocolate. Despite the alcohol, you’re a bit cold, but don’t want to ask for a lumpy yet heat-retaining blanket to disrupt the incredibly curated aesthetic feng shui. This den is so chic, I deserve to be cold. Wrong. Design Friend tosses you a pink and maroon striped mohair throw in a designer-looking pattern. It clashes beautifully with the unique upholstery, and is also incredibly soft. You wrap yourself in it, and become the furniture. A perfect transition from form to function, fun and high design.

You can buy the Porcelain Zodiac Plate 0301 here and the Mohair Blanket 0903 here.

TOM ADAM

PERFECT BRAND FOR: your friend who steals hotel robes on press trips, the person in your life who can’t shut up about breathable fabrics, anyone you know who’s traveling to Lisbon or a similar area in the next year

“Only dead fish go with the flow,” says the founder of Tom Àdam, Tom Vitolins. “Every lifestyle business is about how to do things differently and be authentic. Pajamas were having a huge moment in ’60s Hollywood, and then there was a period where people weren’t taking them as seriously.”

Inspired by Nike founder Phil Knight’s philosophy on a performance running shoe that still maintains a beautiful aesthetic, Vitolins gives us Tom Àdam, a lifestyle brand centered on a linen lounge set inspired by mid-century button up pajama separates. “The beauty of linen is that as you wear it, it ages nicely. The fabric becomes something else entirely—my linen doesn’t shrink, expand, or get a hole, the texture itself changes, says Vitolins.

Is the Tom Àdam Loungewear Set a pajama set or daywear separates? It can be both, depending on how you want to transition your wardrobe. Tom Àdam has also collaborated with a series of ultra-chic hotels including SO/ in Paris, the CERVO Mountain Resort in Switzerland, and The Hoxton in London to keep the luxurious collared pajama spirit alive in all its glamor.

For this holiday season, Tom Àdam is releasing a wonderful line of candles shaped like food: a raw egg, a Moka pot, a baguette. These candles don’t double as food in the same way the loungewear sets double as pajamas. However, they do make a great statement piece.

Find the Tom Àdam Loungewear Sets here and the food candles here.

SUNDAE SCHOOL

PERFECT BRAND FOR: active stoners, reformed stoners who still possess stoner essence, your snackish friends, your friends who need to replace their drug rug with something chic-er

The Sundae Flowers mochi gummies have taken social media by storm over the past year, but did you know about Sundae School, Sundae Flowers founder Dae Kim’s foray into streetwear? Just me?

Not only does Kim produce the flower in adorable gummy form, he makes the comfy clothes that go along with vegging out. “Back in 2017 when I first started the brand, I coined the term smokewear, your uniform for your recreational habits,” says Kim. “Whether it’s the best fitting comfy sweats or an office siren look that makes you both look good and feel comfortable, our team’s design philosophy lies in never sacrificing comfort for style.”

On a spectrum of comfort to style, Sundae School’s Fall Winter 2024 collection meets in the middle with Korean-inspired elastic-backed jeans engineered to accommodate munchies bloating (the Hanbok pants) and extra-plush puffer jackets complete with the “Signature Sleeve” stash pocket for your…gardening tools. From the couch to the deli back to the couch again, Sundae School has got you covered.

“Sundae School’s mission is very simple: We want you to take a break!” says Kim. “In a world that glorifies hustle culture and always pushes you to do more, the best lesson I’ve learned in my 20s is that sometimes you have to chill in order to move forward. Cannabis has been a catalyst to help me relax. Moving forward [with the brand], I’m excited for the team and I to put our foot on the gas pedal and create more.”

You can buy the mochi gummies from Sundae Flowers here, and shop Sundae School’s Fall Winter 2024 collection here.