What To Buy At Free People If You’re Over 40

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We love Free People, but will be the first to admit that their clothing can be…confusing. From the often-bananas styling (bikinis and moon boots while tromping through the woods, as one example), to the inconsistent sizing between pieces and the occasional quality control issue…Free People is tricky. While it’s easy for us to be inspired by Free People, it takes a good bit of work to actually find pieces that fit well and are actually wearable! And we’ve found that this has gotten even more true as we’ve gotten older.

Pieces We Actually Love From Free People

That said, over the past year or so, we’ve happened upon some serious Free People gems – pieces that work on our forty-something selves – and wanted to share! These pieces are all well-made (many are made from 100% natural materials), wash and dry well, fit comfortably, look cute, and are easy to style. I will say the draw to Free People clothing for me is often that they are unique pieces you can’t find elsewhere, so when they do fit, they’re fab finds.

Let’s get into it.


Our Favorite Free People Shorts + Shorts Sets

This is one area where Free People – surprisingly – really seems to get it right. Whether you like shorty-shorts or longer pairs, we’ve found some we truly LOVE.

Free People Moxie Barrel Shorts

Free People Moxie Barrel denim shorts styled with a button down shirt, taupe bag, and sandals

Shorts (29) | Shirt | Bag | Sandals

Details + Fit: I’m very picky about how shorts fit and feel on me, especially as I have entered my late 40’s (nothing squeezing and squishing the waist please) and these Moxie shorts are just about the only denim shorts I care to wear. They’re loose enough in the waist and the legs that they don’t bug and they look cute. A bunch of us love them! I have them in two washes.


Free People Harper Set

Free People Harper cotton shorts set, low-back cut

Harper Set (s) | Sandals (more sizes, here) | Daisy Ring

Details + Fit: Made from a 100% cotton that feels a little thick…almost like canvas (but not at all scratchy – it’s very comfortable!), this set is nice and breezy. It has a seriously cool cut – very fashion-girl kind of lines – and is exactly the kind of product I’m always looking for from Free People. The back is low, but you can honestly wear it with any sort of real bra you don’t mind showing off a lil’. I’m packing this set when I go to Greece, and plan on using it as both a cover-up and as a real outfit.

I’m wearing a size small…so I’d describe this one as being very TTS.

I actually tried on several of these sets in this IG Reel, if interested.


Free People Leandra Shorts Set

Free People Leandra shorts set in thick t-shirt cotton

Leandra Set (s) | Sandals (more sizes, here) | Daisy Ring | Bag | Bracelets

Details + Fit: 100% cotton, this set is fantastic. The fabric is a t-shirt material, but much thicker than your average tee. The top is nice and boxy, and the sleeves are extra-long short sleeves that look so freaking flattering. The shorts have a tie waist, but aren’t squeezy – something that is much appreciated since I tend to carry weight in my midsection. I’m wearing a size small, so the fit is TTS (if not the tiniest bit big).

Free People Leandra shorts set in thick t-shirt cotton

Leandra Set (s) | Sandals (more sizes, here) | Daisy Ring | Bag | Bracelets


Free People Strada Set

Free People Strada matching set with swingy boxy top

Strada Set (s) | Sandals (more sizes, here) | Daisy Ring | Bracelets

Details + Fit: 100% cotton, and runs really snug in the waist. Because I’m only 5’3″, I needed the size small just to get the proportions right – the medium size runs slightly longer and more voluminous. If you carry weight in your middle sizing up might be a good idea, but if your waist is smaller than your hips, this set runs TTS.

The fabric is great – it’s like a really high-quality t-shirt, but a little heavier. Overall there’s a nice heft to the fabric, which is why the top has such great swing and drape.

Free People Strada matching set with swingy boxy top

Strada Set (s) | Sandals (more sizes, here) | Daisy Ring | Bracelets


Free People Sorelle Shorts Set

Free People Sorelle cotton-linen shorts set for the beach

Sorelle Shorts Set (s) | Sandals (more sizes, here) | Daisy Ring | Bag | Bracelets

Details + Fit: 88% Cotton, 12% Linen, this set is really breezy. Free People’s linen does run the tiniest bit scratchy (if you have sensitive skin like mine), but it softens up over time. The shorts closure is just a drawstring, so they’re not at all squeezy on the mid-section. This is just a really fun, playful set that looks seriously cute as a beach coverup, or for wandering into a local coffee shop. The color selection is small but really good, too.


Our Favorite Free People Tops (Tees, Tanks, Sweatshirts, Sweaters & Fleece)

One honorable mention for now…stay tuned for more.

We The Free Take 2 T-Shirt

We The Free Take 2 t-shirt in soft white fabric, relaxed fit

at Nordstrom | at Free People | at Zappos // pearl + leather necklace

Details + Fit: This tee was in my recent article about the best white tees you don’t have to tuck in and I love it. It’s the perfect length and a super soft fabric. It’s a bit sheer which I like for summer, but some of the other colors are not. It comes in quite a few color options and I definitely want more. At under $40 it was one of the lower priced t-shirts I found in my round up.

We The Free Take 2 t-shirt styled with navy satin track pants and blue sneakers

Tee (M) | Pants (M) | Sneakers (tts)


Our Favorite Free People Jeans, Pants, & Matching Sets

This section includes one of our most-worn pairs of denim ever, plus comfy pants and even comfier matching sets.

Free People Pull On Jeans

Free People pull-on jeans in black wash with flat front waistband worn with a cropped green tee

at Nordstrom (blue wash) | at Free People

Details + Fit: These are some of my most-worn jeans lately, especially for the shoulder seasons and warmer months. They’re soft and lighter weight and oh so comfortable with the pull-on style waistband. It’s flat in the front so it doesn’t dig and the hem at the bottom is nice and wide to give them that cool drape at the bottom. I brought them on my most recent trip and they’re so good. I have to wear my shoes with a bit thicker sole to make them work on my 5’4″ self, but worth it.


Free People Moxie Barrel Leg Jeans

Free People Moxie barrel leg jeans in two washes

at Nordstrom | at Free People | at Bloomingdale’s | at Shopbop | at Zappos

Details + Fit: 100% cotton, these are one of my very favorite pairs of jeans, and a good “starter pair” if you are still thinking about barrel or baggy jeans. Even Linzi loves hers! These jeans do run big – I typically size down one size in mine. I’m wearing the regular length here, but they’re now available in tall sizes. I own these jeans in two colors, and they’re the jeans I often get stopped while wearing. They’re comfy, easy, and seriously cool. One of FP’s very best pieces.


We The Free Jetset Knit Pull-On Pants

We The Free Jetset knit pull-on sweatpants in black styled with tee and sneakers

Pants (M) | Similar Tee | Sneakers

Details + Fit: I adore these sweatpants. They’re absolutely leveled up from actual sweats into actual pants and they are something I grab all the time. They’re baggy and have cool details and are just so easy to wear. The pockets make them look like ‘real’ pants or like you tried a bit harder and this is always the goal with getting dressed in my book. Look like you tried when really it was easy. They do run big. I could probably wear a S but like the oversized fit here and the drawstring waist accommodates that.


Free People Miller Set

Free People Miller cotton knit lounge set

Miller Set (s) | Sandals (more sizes, here) | Daisy Ring | Bag | Bracelets

Details + Fit: 100% cotton knit – this one feels like it’s made out of a sweater material, I was actually thrilled (and shocked!) to find that it’s all cotton! It’s super cozy, runs huge (I’m wearing a small and the pants are sliding off – I don’t mind, tho), and is honestly such an unexpected favorite. My husband – oddly enough – loves it, and even my teen boys always compliment this set. Wild.


Free People Hot Shot Relaxed Matching Set

Free People Hot Shot relaxed matching tank and comfy knit pants set in sporty pants with trucker hat

Matching Set (S) | Hat

Details + Fit: This set is so freaking comfy for those days when I’m bopping around in warm weather and just want to be sporty and in pants. I wear the pants a lot mixed with other tops, too. The material is soft and stretchy and lightweight without being too heavy. The pants have a comfy wide waistband. The tank is perfect for popping over a sports bra, cami or swimsuit. The fit does run big. I tried a Medium and wound up sizing down to a Small in this.

dual image of Free People Hot Shot matching set pants styled with black top and sneakers and as a set with a crossbody bag at Animal Kingdom

Similar Top | Matching Set (S) | Similar Sneakers | Slides


That’s it! Have you guys encountered any FP gems you love? Spill! We’d love to know.

xo,

L & S

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