Like a lot of people, I’ve gained about 20 lbs over the year due to changing to a much more sedentary lifestyle and stress eating. I’ve come to terms with this as just how it is, and that likely I’ll be able to fit into my much-missed pants and skirts after a couple of months back in a life with a walk/bus commute and dance classes. But in the meantime, I only fit my leggings, sweats, and a few skirts that weren’t terribly versatile as I’d sized out of my jeans, trousers, and midi skirts.
In order to expand my outfit options in the casual-but-smarter-than-loungewear category, I decided to get some dresses that I could mix and match with my existing cardigans. I trawled the internet for a couple of weeks and eventually settled on a pair of Free People beach cover-ups. Not what I would have guessed I’d end up with, but they ended up working really well with my existing garments, including some that I’d had trouble styling in “real outfits” since their purchase. The outfits have been cohesive yet wide ranging enough that I feel like the collection of items could stand on their own as a seasonal wardrobe, even though I didn’t set out to do that when getting the dresses.
I’ll list the items in this “capsule” (it’s not a capsule in the sense that I’m not wearing anything outside the set, just that it’s a bunch of curated items that mix-and-match really well) then go over why I think they work, and then share the outfits I’ve made so far!
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This is the Free People “I’m Still Obsessed” mini dress. I have it in the colors black and petrichor in a size S, which is my normal FP dress size (I’m normally a size 10 in numbered sizing, but FP usually runs large). It’s from the FP Beach line and I think may be intended more as a beach cover up, as it’s got giant armholes and a deep keyhole closure in the back.
Over the last few months it seems that sizes will go in and out of stock in the various colors, so if there’s one you want, I’d sign up for the email alert or check back periodically. I’ve also seen it pop up on resale on Poshmark, eBay, etc.
If you want to search for similar styles, I think the closest query would be “sleeveless smock dress”, as “pinafore dress” or “jumper dress” usually turns up styles that generally must be worn with a base layer. If you want something more substantial, NotPerfectLinen on Etsy has a few styles with the same energy (midi, button-front, oversized) and you can work with them to customize an order, e.g. shortening overall for petite sizing or adding a simple collar. SondeflorShop on Etsy also has similar items like this smock dress.
The supporting cast
All of these pieces I owned prior to purchasing the dresses.
- Dr Martens Leona platform combat boots
- Birkenstock Arizona in Mocha
- Trotters Lizzie derby flats (these run narrow, go up a category in width):
- Chuck Taylor 70 High-tops:
- Comfortiva brown granny boots (also run narrow, although you may get away with normal width if you don’t intend to pair with thick socks)
- Intentionally Blank white pointed toe lace-up boots
- Marc Fisher “Bowie” black patent leather pointed toe lace-up boots
- Dr Martens 1460s (from the Hieronymus Bosch Museum Collection)
- Blundstone 1673 (not pictured in collage because I forgot and couldn’t be bothered to redo it because they only appear in one outfit so far)
Inner layer tops
- Vila petite long sleeve statement collar blouse EU40
- Urban Bliss jersey ribbed high neck sweater M via ASOS (similar item pictured is Uniqlo)
- Short sleeve black lace blouse (old H&M)
- Free People gigot sleeve waffle-knit thermal S (google link)
- Jurassic Park patch chambray shirt S (vintage via eBay)
- Madewell Emmy Plaid Sunday Flannel (google link) S via Poshmark
- Free People Moon River cropped cardigan S (google link)
- Cream cable-knit cardigan S (old Urban Outfitters cotton cable-knit cardigan via Poshmark, google link)
- Madewell floral sweater S
- Uniqlo U fleece bomber jacket S (google link)
- When not wearing an inner layer, I’ve been pairing these with bralettes or cropped camisoles in rust/black for a neater matching look.
- To prevent chafing, I wear bike shorts. Recently I’ve found myself preferring cotton/spandex shorts for skirt layering as they’re more breathable and aren’t shiny. Ideally I’d like a 4-6″ inseam short with a wide panel waistband instead of a thin elastic. I’ve mostly been reaching for the Free People Hot Shot bike shorts (size M) over my random collection of other ancient athletic and lounge shorts, but while the colorways are really cute I am looking at similar options elsewhere. A lot of reviews mention theirs got holes quickly, though I’ve machine washed and line dried mine a couple times with no issues.
Why it works for me
Relaxed fit – the dress blends more easily with oversized layers or layers that don’t match the hem super closely. I find generally the more structured and fitted a dress is, the more it feels awkward to me when an outer layer doesn’t hit at the traditional hem, waist, or hip line. Think more mori kei style with layers or cardigans and skirts draping over each other and less 00s multi-camisole layering. The relaxed fit also makes it physically easy to layer underneath and should transition if I do end up ever losing the quarantine weight (vs a structured fitted dress).
A waist exists – while I haven’t insisted on fit and flare silhouette for about a decade now, for layering versatility I like that this has a clear bodice/skirt divide so that the overall silhouette is lightly defined when pairing this with baggier outerwear like flannels. Personally, I’m okay with wearing super loose silhouettes, but when it comes to super loose + layered outfits I can start to feel like I’m drowning in fabric.
Larger arm holes – Makes it physically easier to layer. Can work with looser sleeves, and the sleeveless cut means I don’t have to figure out how to stuff any voluminous sleeves into fitted outerwear.
Textured fabric and gathered skirt – While the dress is fairly minimal in design and a lightweight knit, it’s thick enough not to show every single seam and bump of a shirt beneath it, and the earthy linen-like texture and substantial amount of skirt fabric give it enough body to feel like a proper dress and not a flimsy beach cover up.
Wearable as-is – I tend not to reach for pieces that must be paired with a cami or a specific cut of cardigan. I’m lazy and my closet is a mess, the chances of finding the corresponding piece are slim. I wouldn’t wear this without additional pieces to an office setting, but I’d wear it to answer the door or if it’s warm enough, around the neighborhood. Given that I’m going to be WFH for the foreseeable future, that works for me.
The surrounding items
Mix of inner and outer layers – nice for style variety and also temperature. If this was unwearable without a base layer, I wouldn’t get to wear it during warmer days.
Mix of dressy and casual – to cater to my capricious fashion whims, both the shoes and the tops can be combined from styles ranging from dressy goth to camp counselor due to the mix of utilitarian and cutesy pieces. But for the most part things are either utilitarian-casual or cute-casual, not all out camping techwear or Event Dress, so they can easily coexist.
Mix of colors and color values – this is really important for me to not get bored with things. For other people, the styles or silhouettes might make a bigger impact, but high contrast combos in different configurations just feels the most different to my brain.
Fair-weather friend – You may notice that I have bare legs in all of these outfits. I’ve tried pairing these with tights a few times, and I always feel that the overall vibe with the knee length skirt is too conservative looking for me. It’s not so off putting that I wouldn’t throw on a pair of thermal tights with the long sleeve combos in a pinch and just enjoy the color combo, but I would rather pair opaque tights with a true mini for a more youthful look, or with a full midi skirt for a more vintage inspired style and more dramatic proportions. We’ll see if my mind changes come colder weather, but if it doesn’t, there’s always layered leggings with sweaters.
Casual – Due to the earthy and casual fabric of the dress, I don’t think I would wear it to any event with a cocktail dress code or fancier. It can definitely be dressed up especially with the lace blouse and more feminine shoes, but only to a point if considering traditional markers of dressiness. This guide from the Gentlemen’s Gazette despite being tailored to (hah) menswear has a good overview of how to evaluate color and fabric. Although YMMV for anything cultural like this. I live in the Bay Area, where you wouldn’t get kicked out of watching an opera if you showed up in jeans and a tie dye shirt but I love an opportunity to dress up! Again, for personal style this doesn’t matter, but dress expectations are sometimes a thing and if for some reason I needed a more all-occasion capsule I probably would have gone with something like a ponte shift dress.
With base layer
Without further ado, the outfits:
Ready to run through town or the forest for a cute adventure
Goth Girl Goes to Garden Center
Getting some vague academia style vibes from the trouser sock + derby combo and the mock neck (which I know isn’t terribly visible here)
But now make it ~witchy~ (it’s carried by the boots)
Gigot + grunge. I feel like my head seems small compared to the outfit, I might add a white headband if I do this again.
Slightly spooky/autumn vibes
ft. cute bat necklace from TheWoodsOfWonder
The dressiest option
With outer layer
aka basic layering, I don’t have that much to say
Check out how much the shoes change the look though
Again, just shoes and hair changed! It’s not like I look like a totally different person, but imo it’s at least a totally different energy.
The socks really tie it together
Kind of an art student thing here
We have reached the button-downs! A casual light grunge sort of thing. I want to try this with the black dress and a colorful sock at some point.
Light side vs dark side flannel looks
17 outfits and counting, and I don’t feel like I’ve nearly exhausted the options. It’s been a long time since I got anything that meshed this well with so many existing pieces in my wardrobe, so even though it’s been a few weeks I am still completely chuffed at how great these have been to mix things up. I’d previously had a hard time wearing the button down shirts outside of loungewear because they always felt too masculine or shapeless for my taste, but I really like them with the shorter dresses! And importantly I’m glad I like them with my three current favorite walking shoe options: the Dr Martens Leonas, derby flats (not for like, hiking grade walking, but fine around town), and Birkenstocks. I like to think of these as “Ghibli Girl” dresses because they have a kind of free-spirited adventure-ready girliness to them which is easier for me to wear than other fantasy-based aesthetics like all-out cottagecore, mori kei, or light/dark academia.
I’ve mostly been alternating between these outfits and straight-up athleisure the past few weeks and I haven’t been this happy with my wardrobe in a long time. I don’t know why it took me so long to get into layered dress looks, but I’m glad I did now. What better time to experiment with style than WFH anyway?
I was originally intending to keep upsized purchases to a minimum but I LOVED the sleeveless options so much, I ended up getting the sleeved versions too (one from Free People directly to confirm fit was the same in size small, the other from Poshmark) so I could roll into video calls or breezier weather without layering. I am 100% here for the big sleeve macro trend we are in the middle of now so the frolicking-ballet-background-peasant sleeves were definitely a plus. As usual these are like 2 inches longer than I would ideally like, and I might hem them someday, but even with that I’m still really stoked about these because they feel like the most mgetsdressed dresses ever.
Thanks for checking in! Have you had any quarantine-induced style revelations in the last few months? Let me know in the comments!
I love feedback! Feel free to leave a comment below on whether you found this post interesting or helpful, even if you don’t elaborate on it 🙂
For more analysis in a similar vein, check out these previous posts 🔬 Learning From Miss Louie’s Capsule Wardrobe Formulas and Tips for maximizing the visual interest of a capsule wardrobe