
As much as I love getting dressed up, I am team cozy and comfy. I get dressed up a few times a week if I have fun plans, but the rest of the time, I just want to be comfortable! Be it jeans and a tee, really good cashmere, or a cushy pair of wide-leg sweatpants, I’m happiest wearing laid-back pieces. Today, I’m sharing a round-up of super comfortable outfits. I hope you enjoy!
Speaking of comfy, cozy, I just found out that Lake Pajamas made us a code! GracexLAKE gets you 10% off sitewide. My favorite easy set is now available in dark green and black, and this is the best robe ever.
PS – you might also enjoy: the correct order to apply your skincare products, last year’s winter knitwear edit.
8 Comfortable Outfits

Wide leg sweatpants + mary jane flats
I cannot shut up about Mirth’s ultra-comfortable wide leg sweatpants. They are the best. (We have a code too — GRACE15).
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Heavyweight TeeThis COS tee is so great. I love the slightly thicker, heavier weight fabric. It gives it some nice structure!Shop
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Lounge PantsThese are just so extraordinarily comfortable. I love them so much.Shop
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Ballet Flatsthe cutestI wear these so often and the leather is so soft.Shop
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Lip TreatmentA plush lip balm with just a bit of color.Shop
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Gold Link BraceletPerfect for everyday.Shop
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Face Moisturizermy favThe best moisturizer ever ever. I love this stuff.Shop

wide leg sweatpants + stripes
I was half awake when I took this photo, but I wanted to show it here so that you can get an idea of how the wide-leg sweatpants look on. This is one of my most favorite striped tees.

barrel jeans + fun sneakers and a cute top
One of my favorite things about the new barrel jeans trend is how comfortable they are! Here, I styled a cute top with my Everlane barrel jeans (these are really cute + a great price), lurex socks, and my super special Chloe sneakers. Hair gets scraped back in a bun because sometimes you just can’t be bothered.
With regard to the Chloe sneakers, sometimes I won’t invest in basics like sneakers and tees. I’m so glad I did with these as they make even the most boring outfits feel special.

cashmere monster
I was gited this sweatshirt and these wide leg pants from Garnet Hill earlier this season and I cannot get enough. They are just the BEST but also… machine washable! I need more washable cashmere in my life, this is a gamechanger because I like to sit all day in my cashmere. I love that I don’t have to be precious with this set!
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Diamond StudsA classic!Shop
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Cashmere SweatshirtThe comfiest and it’s washable!Shop
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Cropped PantsfavoritesThes are just the best. I want to snag more colors!Shop
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Crew SocksRed socks look so cute with this ensemble!Shop
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Suede Loafersthe bestMy most favorite loafers! I’ve got black, red, and tan!Shop
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Face Maskthis is so goodThis face mask is so good, especially after a long flight. It puts the moisture back into dry, dehydrated skin!Shop

Stripes & slippers
This one is perfect for lounging at home, doing your skincare, watching a movie, ETC! I love this Amazon set so much. Mine has held up fabulously in both the washer and the dryer (not always the case) and it’s perfect for a cozy night in. Add a fun sock (and a coordinating clip), cozy sherpa slippers, and boom. You are ready to vegetate, in the cutest way possible. For extra credit, pour yourself a glass of wine and slap on my favorite eye masks!
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Claw Clipfun!The cutest claw in one of my favorite colors.Shop
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Striped SetinexpensiveThe best cozy set; I love this!Shop
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Ribbed SocksIf you don’t match your socks to your hair clip, what are you even doing? 😉Shop
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Eye Masksbest affordable gemThese are an incredible price and make such a difference for bags, brightening, and fine lines.Shop
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Dome StudsTop off your cozy look with a fun earring!Shop
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Sherpa SlippersSuper sturdy and very comfortable!Shop

tee + shorts, with pops of red
I am a big fan of making my comfy outfits feel a little pulled together by adding a pop of a bright color (chartreuse and yellow also work nicely). Case in point: the scrunchie (a Mango gem!) and red sweater. Also, I’ve gotten very into Guest in Residence. It’s Gigi Hadid’s brand, so that cracks me up a little but their cashmere is so super soft! This pullover has such pretty pointelle details. I also have this striped pullover and love it so much. Red and burgundy make a great team.
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Cashmere Pulloverpretty detailsThe coziest and it has the prettiest pointelle details up close!Shop
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Pointelle Teegreat basicThis is such a pretty tee. Definitely size up, I wear the largeShop
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Mid-Rise ShortsMy favorite cutoffs are on sale!Shop
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Flower Scrunchiefun touchThis cute scrunchie makes for such a fun touch!Shop
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Drop EarringsA great basic!Shop
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Buckle Sandalson saleThe best sandals. I’ve worn these to death and they are now on sale!Shop

colorful wide leg pants
I wore this outfit to the movies with friends, and it was so easy (and comfortable). And these pants are the best ever. My sister recently borrowed them to wear for her trip to New York, and I miss them. (We have a code, by the way — use GRACE10.)
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Wool SweaterCute and comfy. Tie it over your shoulders or bundle on up.Shop
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Striped TeeHands down, my favorite striped tee!Shop
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Straight-Leg Pantsthe bestThe coolest pants! Use GRACE10 for a discount.Shop
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Claw ClipA cute little claw to clip hair back.Shop
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Quarter SocksMy favorite quarter socks.Shop
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Suede SneakersChloe’s sneakers are the coolest. They are a big splurge but I wear mine so often.Shop
Disclosure: If you buy something through my links, I may earn an affiliate commission at no cost to you. I only feature things I truly love here. Thanks for your support.
Comfort is KING! As I enter my 50s, I find myself spending more money on quality, comfortable clothes. I want to be swathed in beautiful cashmere with chic trainers and simple, but elegant REAL jewelry. I want flattering jeans (not so easy these days) and pretty leather driving moccasins or ballet flats. I want to look luxuriously COMFORTABLE, like a Hollywood actress on her Saturday off.
Everything you said!
Thank you for showing your “half awake” photo. It is obvious that your skin has been properly cared for through the years and you look beautiful even w/out makeup. I turn 40 next year and have been struggling a bit with my skin and its changes plus all the changes that come w/ just getting older body wise. Sometimes seeing other women who are “older” than me in natural photos is a good reminder to myself that proper skin care + a combo of other things pays off down the road and we don’t always have to be camera-ready at all times in order to be beautiful. And, turning 40 (or even 50/60/70…..) doesn’t mean we have to lose sight of the cool stuff. 🙂
P.s. Can’t wait for this year’s gift guides!
🙂 40 is young! xx