We’re Feeling Nostalgic in Ashlee Simpson’s Retro Collab

“On a Monday, I am waiting. Tuesday, I am fading. And by Wednesday, I can’t sleep. Then the phone rings, I hear you—” Oh, sorry, just bopping out to a 2004 hit. If you too grew up singing along to the angsty “Pieces of Me” by Y2K teen idol Ashlee Simpson, then this is the place for you. The singer turned reality TV star turned fashion designer has come out with a new collection entitled, yep, you guessed right: Pieces of Me.

The sweetly named collaboration with female-founded brand Smash + Tess reflects what Ashlee Simpson Ross loves most: her husband and children. So the collection fittingly includes styles for women, men, and kids, particularly jumpsuits and overalls. (And you better believe Ashlee and her family modeled them on-site, too!)

The laidback retro-inspired pieces come in a muted ’70s-esque color palette that’s both classic and versatile. The womenswear styles are also available in Smash + Tess’s standard inclusive sizing (3XS through 4X) to ensure as many of us as possible can add a piece of Ashlee to our wardrobes.

Inspired by what Senior Writer Karina Hoshikawa perfectly describes as Ashlee’s iconic “rocker-meets-boho style,” we on the R29 Shopping team were excited to try some S+T X Ashlee Simpson Ross Pieces of Me styles. See our looks below.

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Far Out Overalls in Groovy Grey, $150

“As a millennial girlie who loves overalls — and had multiple Ashlee Simpson bangers burned on her ‘middle school anthem’ CD mix using Windows Media Player (what a throwback) — these Far Out Overalls are a revelation. The baggy silhouette feels super-comfortable to move around in, and the stretchy cotton-spandex fabric is a lot less cumbersome compared to denim overalls, which are usually way heavier and more rigid in construction. They were cozy enough to lounge around the house in but also give enough casual chicness to wear for a weekend outing.

“The heather gray color looks great with basics like a solid black turtleneck or a nautical striped bateau top. Full disclosure: The legs are quite roomy, and with an almost 29-inch inseam, they really dragged on the floor for me. So I’m fully planning on taking these in a couple inches at the tailor’s. Miss Simpson, however, wore hers loose with the hem touching the ground — so it might be fine if you’re a bit taller (and cooler) than me and into the baggier, Y2K-inspired look. I would recommend going a size smaller than what you usually wear since I personally prefer the top half of the overalls to be a bit more form-fitted.” —Venus Wong, Senior Travel Writer


Disco Slip Dress in Cool Cream, $120

“Normally, I’m wary of slip dresses as I like dresses with more structure to shape my body; however, I was quite enchanted with this elegant floral patterned pick designed by Ashlee Simpson Ross (BTW thank you very much for your contribution of ‘Pieces Of Me’ to my childhood). The dress was very soft and comfortable, almost like a nightgown and I recommend sizing up if you have a bigger chest. It paired perfectly with a belt to accentuate my waist, and my boots for a retro-modern take on the Western aesthetic.

“I love how Ashlee Simpson Ross created a collection for her whole family with pieces to match her husband and children and just HAD to see if the pieces actually looked good with a significant other, ergo, see my boyfriend Louis’s thoughts below:” — Becca Sax, Affiliate Coordinator


Radical Button Up Romper in Vintage Brown, $160

“To be honest, I was very apprehensive about this jumpsuit. My normal style is more like Air Maxes, fitted cap, and maybe a logo hoodie from the one or two brands I like. So I was really surprised with how much I liked this jumpsuit and how natural it looked on me. I’m a small guy (5’5”, 135 lbs.), so I got an XS, and it’s still light and airy in a very nice way.

“I honestly want to wear it around the house just to lounge around in. I could see myself wearing this to a day party with a pair of brand-new white sneakers. It’s also great for letting a couple buttons loose with a fresh white tank top underneath. I’d wear this to a summer night party, too, and undo the top, tying it around my waist with a white undershirt for a night of sweaty dancing.” —Louis


Wicked Wide Leg Romper in Vintage Brown, $150

“I don’t really own any jumpsuits or overalls, so since this collection is chock-full of them, I decided to try one out for myself. I opted for the Wicked Wide Leg Romper, choosing brown since it’s a shade I think I can pull off both in the spring and fall.

“Ashlee is seen modeling the romper with a slightly baggy, relaxed fit. But my suggestion is that if you want to have a more snug fit, go down two sizes from what you typically wear. I initially ordered a large, but the proportions were too large in the chest area and too long, so I sized down to a small. While it slightly tugs around my hips, the material is stretchy, and I still have room in my chest and shoulder area, so I don’t feel constricted.

“The retro front zipper adds some extra interest and makes for easy on-and-off access, which I really like. But I actually love the back of the jumpsuit the most. I think if you saw me from the back down a street, you’d be like, “Wow, that girl looks like a cool, hipster mechanic,” and I’d be thrilled that you thought that! I can see myself wearing this retro one-and-done jumpsuit for some weekend ventures when I don’t want to stress about assembling an outfit and want to ensure I’ll be comfortable all day long.” — Victoria Montalti, Associate Affiliate Writer


Disco Slip Dress in Cool Cream, $120

“As someone who grew up with Tiger Beat and J-14 posters on my bedroom walls, Ashlee Simpson’s collab with Smash + Tess truly spoke to my angsty pre-teen soul. When I think of Ashlee, I immediately think of her rocker-meets-boho style, which definitely comes through in the collection. However, the standout piece for me was without a doubt the Disco Slip Dress. For starters, I absolutely love a slip dress — so simple, so chic! — and the V-neck and midi length looked so pretty on Mrs. Simpson Ross.

“(Also, I’m on the petite side, so the fact that they had smaller options was a definite win for me!) The XS was true to size and the ivory, brocade-esque fabric had such a cool vintage vibe that I loved all on its own (but if you get chilly, it also pairs well with a denim jacket or oversized cardigan). My fiancé said it looked like I was wearing an expensive curtain — which I can only assume he meant as a compliment. I for one can’t wait to wear it out on dinner dates and rooftop drinks this summer.” —Karina Hoshikawa, Senior Writer

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