It could be pajamas. Or it could be athleisure — albeit the most comfortable athleisure you ever did see. And yet…she’s wearing it with a leather jacket. So confusing!! Welcome to the world of Ambiguous Sleepwear. Comfy enough to sleep in, street enough to wear outside.
The term “Ambiguous Sleepwear” is a genius term, coined by my friend Marisa’s mother. And it’s so freaking apt — it’s basically taking Athleisure next level. And who doesn’t want a pair of Outdoor Sweatpants or an Oversized Hoodie or a Sleeping-In-Strolling-Around Sweatshirt?
Three Outfit Ideas Starring Ambiguous Sleepwear
1. The Softest-Ever Sweatpants & Sweatshirt by Beyond Yoga
This set has quickly become my go-to for travel, simply because it IS the set I put on every night. It’s insanely soft, thin, drapy, and flattering. Which is the real reason it’s so good for travel. I can lounge around in it at night, and still look presentable enough for a morning coffee run. So if you haven’t yet discovered the magic that is Beyond Yoga…this set is a great place to start.
jacket: IRO Leather Moto Jacket (size 38 – size up to fit under sweaters)
sweatshirt: Beyond Yoga Cropped Turtleneck (size xs)
sweatpants: Beyond Yoga Foldover Sweatpants (size xs)
sunglasses: Le Specs Weekend Riot – love that these are almost rubbery — they’re super-durable, hit that sort of sporty-glam vibe, and I end up taking them everywhere. (Under $100, too.)
2. Skinny Sweatpants…In Pink
The Free People Kyoto Leggings are, in fact, sweatpants. Just skinny — yet comfy — ones. And they are — by last count — the MOST beloved sweatpants on the planet (I took an informal vote). It really comes down to the bum, but the wide range of color choices doesn’t hurt either.
sweatshirt: Free People Pullover (xs) – Isn’t this just fun and cute? Also in white with black stripes. (And FYI – this sweatshirt is also super-soft with a really flattering fit.)
sweatpants: Free People Kyoto Leggings (xs) – I’ve been wearing black ones for YEARS. (First seen here.) And truth be told, I’ll never EVER quit my black sweats…but the pink have been really fun for a fresh little upgrade.
boots: Stuart Weitzman OTK Boots – People ask me all the time if these boots are worth the price, if they actually stay up, etc., YES. These have been my most-worn boots all winter for the past 2? 3? years running. They make skinny jeans toasty, skirts and dresses comfortable in freezing temps, and they can even save sad leggings outfits. Love. Them.
bag: AER Fit 2 Backpack – still my fav for daily use
3. Matching Tweed Leggings & Hoodie
LOFT’s tweedy little set has been the most perfect thing for pick-up and drop-off. I sized up on the hoodie AND the leggings — they’re comfy, but don’t stretch quite as much a regular leggings.
sweatshirt: LOFT Tweed Hoodie – size small – Size up for a properly oversized fit (more sizes available at…Nordstrom? Weird but true.)
sweatpants: LOFT Tweed Leggings – size up!!
boots: Stuart Weitzman OTK Boots -People ask me all the time if these boots are worth the price, if they actually stay up, etc., YES. These have been my most-worn boots all winter for the past 2? 3? years running. They make skinny jeans toasty, skirts and dresses comfortable in freezing temps, and they can even save sad leggings outfits. Love. Them.
bag: AER Fit 2 Backpack – Still my fav for daily use
Shop My Favorite Sweatpants, Sweatshirts & Other Cozy Pieces
Since taking these pics…there have been some upgrades to the core pieces, and many are totally worth considering. For example: LOFT has just released a TON of shapes in the tweedy boucle fabric (sweatshirts and sweatpants and ponchos — in addition to my leggings and hoodie)…and many are now available at Nordstrom. My Beyond Yoga stuff is available in several pretty colors…but each retailer seems to only be carrying one, meaning you’d have to HUNT THE INTERNETS to see all of them.
Which is where we come in.
So. Below are the pieces that I’ve either featured above, are related to pieces I’ve featured above, or were so freaking cute/comfy/cozy that I had to include. Enjoy!