Winterizing a Maternity Dress: 2 Formulas with Isabella Oliver



Oh. Heyyyy. Still pregnant. 30 weeks pregnant, actually. Meaning I’ll be achey, tired, bloaty-ish and uncomfortable in the majority of my clothes just in time for the holidays! GREAT. Awesome. Can’t wait.

On that cheery note ha-ha, I started to experiment with different ways to stretch my maternity wardrobe and make it all work for me until the very wonderful end – especially during the holiday season when everyone is looking all fab-u-licious and I’m pining for my sweatpants. So, I think I’ve found one winning way to make my options work (and stay out of the sweats, mostly): winterizing a maternity dress. AKA making a maternity dress that isn’t necessarily a Fall/Winter style wearable during colder weather. It doesn’t stop at just wearable though, ladies. We’re talking warm enough but also ROCKIN’. I settle for nada less.

I put two looks to the test and found it’s all about LAYERING (and a bangin’ lip color doesn’t hurt).

Formula #1. Pullover Sweater + Tights + OTK boots

As soon as I pulled the sweater over the dress…YEP. Instant illusion that I’m wearing a cute, little mini skirt (almost) + the tights and sexy over-the-knee boots? Oh, heck yes. I got so excited about this one that I even did a little celebratory dance around our room. Just so you know.



I added the festive clutch because it called to me in Target saying, “I’m spaaaaaarkly, oh-so-chic and perfect for that fake party you’re not going to!” SOLD.





dress: Isabella Oliver Kerwood Maternity Dress – like most Isabella Oliver dresses, it’s extremely comfortable and has a way of flattering the bump like nothing else. (wearing a size 2).

sweater: Target Pullover Turtleneck Sweater (wearing size Large) – the color and turtleneck style are perfect to pop-over this dress. If you’re looking for something a bit better quality, I’d consider the Classic Turtleneck Sweater from J.Crew (in a size or two up). I love Target, but can already tell this one’s a few-wears-only sweater.

boots: Dolce Vita Neely over-the-knee boots – my beautiful, sexy loves. They’re a cheaper option for those of you drooling over the Stuart Weitzmans without that kind of boot-fund in the bank. Granted, the DVs are still a pretty penny (or two…or three) but if you want a great pair of OTK boots these are lovely and worth considering (quickly, because they’re selling out. no pressure. haha!)

clutch: Jeweled Convertible Clutch – the perfect amount of bling bling. Have an actual holiday party to go to? You cool person, you. Go for a fun bag like this that you couldn’t usually wear when the kids are in tow.

lip color: Revlon Just Bitten, Lovesick – I’ve been buying the Revlon lip colors for a while now and I’m a fan. They never feel weird on my lips (ya know?) and they always have new, fun colors coming out each season.

Formula #2. Cool Jacket + Leggings + Moto Boot

I’ve always loved “roughing up” more feminine outfits with a little grunge (or whatever you want to call it). The Isabella Oliver dress is definitely a more dressy style, but I figured: hey, if I could successfully make it a bit more casual and tomboyish that would be so cool. I threw on a few different layers and some serious moto boots and done. Dress made casual.



Leggings. I’ve been surprised by how often they’ve come in handy this pregnancy. I’ve been wearing them under dresses (that are a little too short), long tops and sweaters or at home with a sweatshirt. I can see that I’ll be getting a lot of wear out of them postpartum, too… like when it’ll still be chilly outside and I’ll have my bum planted on the couch while nursing, nursing, aaand nursing (oh, and also trying to wrestle the other two kids that reside here and their needs).





dress: Isabella Oliver Kerwood Maternity Dress – same as above. If you’re not digging this particular dress and pattern they’ve got quite the selection of maternity dresses. I can’t recommend them enough for all of you pregnant mamas.

jacket: Levi’s Lightweight Jacket – SC is weird with its Fall/Winter weather. Some days are chilly and then other days are mild but I still want something to layer over my tees, etc. I’m a lover of military style anything and this jacket is lightweight enough to work the current weather around here. I still plan on wearing it once it gets colder, but over a sweater.

boots: Frye Veronica Shortie – goodness. Frye. You know how to make a darn boot, don’t you? I’m also digging Vince Camuto’s Pierson Moto boot though…OH!…andand the Roadell toooooo. Sheesh. 

leggings: Blanqi Belly Lift & Support Leggings – well, Blanqi is a great company (started by two rad moms, from the ground up)…not only that, their products for pregnant and postpartum mamas are incredible. This particular pair of leggings gives me that bit of lift/flattening I need for my rear end. Seriously. My bum has reached another bubbalicious level this past month. Ha!!

gloves: Target fingerless gloves…aaaand can’t seem to find now (maybe sold-out online), but J. Crew has these ribbed wool glittens (and they come in a few different colors).

bag: Sole Society, old. Their new Black Foldover Tote is a great one and holds a bit more (hem kids and their shtuff). I won’t be able to get away with carrying just a cross body soon so it’s back to the bags that hold everything come January!

lip color: Revlon Just Bitten, Lovesick

Oh, baby. I am…so tired. Exhausted, really. In fact, I am ready to call it a day and climb into bed at the early hour of…oh, 12 pm. I’m such a partier these days. I bring the house down…or the bump down…in my bed. Partaaaaaaaaay.

I just realized I sound so positive about this pregnancy and baby. heh. Well, I am a sarcastic nincompoop most of the time…and so I joke that way. I have to say though, I am so so so incredibly excited about this baby. I CANNOT wait to meet him. I daydream about that moment right after birth, when they’ll lay him on my chest and I’ll breathe that big, long sigh and feel his warm little body on me. The smell of his little head, his tiny breaths. How much love I will feel for him all within those first few moments. It’s simply the best. It’s amazing.

No matter how difficult it may be with three (and gosh, I am scared), I know that our lives can only be enriched even more by his little life. I wonder what his personality will be like. AH! I can’t wait.



ps. I used my own snazzy hair tutorial for those easy waves. Yeh, I’m what you’d call a Youtube hair expert now. Ha. Totally.


photos: Brandon Brown Photography


  1. Love the dress! I’m 33 weeks, so I feel your pain as the holidays are approaching and I’m not allowed to wear leggings and an oversized T-shirt to Thanksgiving OR Christmas 🙁 I am also obsessed with the Ingrid & Isabel dresses too, I style them so many different ways and can still be comfortable! Great post!!


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