Styled, Three Ways: Free People’s Oversized, Floral Sweatshirt

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A reader (Hi, Monica!) left a comment on a recent post, saying that she had bought this oversized, floral sweatshirt by Free People, but needed a little help styling it.

First of all, I can see why.  The slightly nuts print is everything.  It’s ‘florals for Spring’ done in a completely unfussy way, and I love it.

Anyway, Monica bought the black, so I did too, but I the blush color is also fantastic.  The blush will read a little more romantic, a little less eccentric.  The darker floral rocks that ‘grandma’s curtains’ vibe hard.

I’m totally digging that vibe.   Here’s how I styled mine….

Flares Are The Main Thing Here

The sweatshirt is so huge, it’s almost dress-like.  So I took it in a Dress-Over-Pants direction, and the best pants for that kind of job?  Flares.  Since it’s early Spring, I added my favorite (and insanely comfortable) Sorel 1964 wedges, and layered the whole thing over a ribbed turtleneck, cause that’s how I do.

Add parka, done.


Outfit Details

Sweatshirt: Free People Go On Get Floral Sweatshirt (size xs) – this is selling out at Nordstrom and Shopbop…but there are full sizes still in stock at Macy’s and Tilly’s.

parka: S13 Canyon Parka (size xs for reference) – on major sale!

turtleneck: 525 Ribbed Turtleneck (xs for reference)

flares: JBrand Lovestory Flares – mine are years old, but JBrand just reissued them.  Also at Nordstrom, Shopbop (lighter wash), or Amazon (darker wash)…and there are a few left of this medium wash (on Amazon).

boots: Sorel 1964 Wedges – this wedges were an epically good buy.  As comfy as sneaks, yet surprisingly high.  I first mentioned them here, and since then, readers have also been raving about them.  A few sizes/colors are on sale at 6pm, too.

sunglasses: McQ Hexagon Brow Bar Sunglasses


Cropped Jeans + Sneaks

To play up the casual, almost boyish vibe of the oversized sweatshirt, I wanted to pair it with converse hightops.  So I used my long-short rule:  long tops almost always look cute with cropped pants.  In this case, the ripped, cropped denim reinforced the Tomboy vibe of the hightop (while showing it off nicely).  This pairing even works in cold weather (I hate cold ankles).

To keep myself from drowning, visually, I pulled my hair up and added a slim black choker to draw the eye.

Outfit Details

Sweatshirt: Free People Go On Get Floral Sweatshirt (size xs) – this is selling out at Nordstrom and Shopbop…but there are full sizes still in stock at Macy’s and Tilly’s.

jeans: AG The Legging Jeans (size 24 for reference – this wash stretches)

sneakers: Converse High Tops – also at Amazon

choker:  Vanessa Mooney Tibi Choker


As A Dress??!!  YES.

I’m so short that I can easily wear this sweatshirt as a dress.  However, if you are taller than my 5’2″ (so basically the rest of the world), then stick a pair of shorty-shorts underneath.  As long as an inch or two of hem peeks out, it works.  Denim cutoffs would work the best, but a little skirt would be cute, too.

Another option?  Leggings.

But regardless of your leg options (bare, shorts, skirt, leggings)….to keep the vibe that sort of effortless, sexy-boho, you really need a pair of flat, over-the-knee boots with this.  Mayyyybe tall boots would work.

And I like to balance it all out with an oversized scarf.

Outfit Details

Sweatshirt: Free People Go On Get Floral Sweatshirt (size xs) – this is selling out at Nordstrom and Shopbop…but there are full sizes still in stock at Macy’s and Tilly’s.

scarf: old (and moth-eaten, shhhh!) – try this Betsy Johnson wrap or this gorgeous cashmere wrap (on sale, nice and big, and in a zillion colors)

boots: Stuart Weitzman Lowland Boots (also at Nordstrom) – for a more affordable option, try the Dolce Vita Neely boots or Sole Society’s Valencia boot.

bag: mine is really old….but Sole Society has a fur bag in gray or blush.  It’s round and cute and ridiculous.  Perfect.






About Author

Shana founded The Mom Edit in 2008. She lives with the love of her life (his name's Mike) and their two crazy boys in downtown Philadelphia. She loves a good styling challenge (her engineering side shows eventually), appreciates kindness, and usually picks scotch over wine, sneakers over stilettos, and denim-underwear, always.

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  1. I have the exact same sweatshirt. I love it. So print-striking and sooooo soft and slouchy and cozy. I pretty much stick to leggings, skinny jeans or cropped girlfriend jeans (a touch slouchy but not baggy). I’m noooooot so sure that this can pull off as a dress even on a shorty. I don’t think I could really pull it off with flares but the flares look great on you with it. For anyone interested in purchasing, I’m a size 4-6 and usually a “small” in things but even the extra small fit me like an “extra large” so size down one size and you’ll still have a “very oversized” look to it.

  2. I especially love the flares! Would you consider doing a piece on what to wear with different style jeans? I have medium wash flares, dark high rise skinnies, and this new cut from J Crew called Rayner jeans (they show them with heels, but I was gonna try to go ballet flat or cool clogs). I’d love your take on good pairings with each style of denim.

  3. Shana……you are the bestest ever!!! Thank you soooooooo much! I have a pair of flares, and cropped skinnies. I’m too tall (5’8″) to do the dress, but will definitely try with my denim shorts. Thanks for helping me take grandma’s curtains from frumpy mom who gave up to fun mom with some style!

  4. This is SO good! I love the first two options. The third, well, I’m not sure about the third. It looks a little bit like you…forgot your pants? I might applaud it if I saw it in person. Letting a little hem peak out (denim) would look awesome. Also, I would never wear a dress or skirt that short with kiddos around. I’m always leaning over and then WHOOPS. You know?

  5. Rosanne Green on

    Your 5’2″?! You photograph like you’re 5’11”. Now I love you even more. (Appreciate your work on this blog!)

  6. Love them all! Especially with the jeans – there’s something so cosy about a long jumper with skinnies and also I’ve ALWAYS loved a long top with flares, especially on a great pair of legs like yours!

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