What to wear with a spring dress in winter

I'm going to Miami this weekend for a girls' trip with some of my oldest friends, so while it's still technically winter, I have beach weather on the brain. Also, I have so many cute spring and summer dresses, it's a shame they have to languish in my closet for months. So today I'm breaking all the rules and wearing my warm-weather dress now. Take that, January!

This dress was a Cyber Monday score; I've had my eye on it for months and it recently came back in stock with an offer I couldn't resist. Between the shape and the embroidery, the sleeves are kind of over-the-top, but I think they're actually really flattering in that they're so big, they make the rest of your body look smaller! It's also been ages since I've worn an empire-waist dress—like since the '90s—but since the hem is banded, it helps contain the wide shape. One thing to note about this dress: it's quite short, and I actually had to let out the hem. It was an easy fix though, and I'm thinking of doing a tutorial on Instagram stories!

The biggest aha moment here was the over-the-knee boots. Pretty much every blogger I follow on Instagram has a pair (or several), so after years of thinking they weren't for me, I finally caved and bought a pair on major sale.  This was the first pair of over-the-knee boots I've ever owned, and I love them so much, I'm kicking myself for having not bought a pair sooner. (But I plan on making up for lost time by wearing the heck out of them this season.) They are easy to get on and off, the heel is totally walkable and comfortable, and my favorite part is that they go up so high, I don't even have to shave my legs!

I'm a believer that your accessories should coordinate but not totally match (so 1950s), so to harmonize with the taupe suede of my boots, I picked this camel leather crossbody (last seen here), which holds a lot more than you'd think. Circular bags are still on trend this year, and this one is really reasonable for the quality of the leather. Plus, it's by Baggu, which is a local San Francisco brand!

Since this dress has so much going on, I kept my jewelry simple and delicate. These are two of my favorite necklaces—they layer together nicely, and since there's a mix of metals, they pretty much go with anything. Same with my favorite X ring and Miansai screw bracelet—you've seen them here before, and you'll see them again!

So, I realize I'm lucky enough to live somewhere that I can be outside in January and not have a coat on, so I'll try to keep my winter complaints to a minimum. But I will think of you all fondly while I'm sipping umbrella drinks on the beach in Miami!

OUTFIT DETAILS: Free People Mini Obsessions dress || Sole Society Catalina boots || Baggu circle purse || Stella & Dot Luna pendant, Abundance necklace || Miansai screw cuff || X-ring || YHF Los Angeles Cashton sunglasses


Patti said...

Such a charming dress, and the OTK boots are terrific with it! Thanks for linking up, xo


Unknown said...

Love the embroidery. I think it totally works in winter. Have a blast in Miami!

Laura B said...

Gorgeous dress! Love how you made it work for colder weather!

RuthyAnnie said...

This dress is absolutely beautiful. I love the embroidery on the sleeves and how you paired it with the OTK boots.


Unknown said...

Yes girl, break the rules! Why wait for Spring with a dress that cute? Especially in Miami: I feel like there's totally a fashion exception there! I definitely agree that the accessories should harmonize but not totally match! The taupe purse is a win with those stellar over-the-knee-boots!

~ xo Sheree
Posh Classy Mom

Clairejustine said...

Such a pretty dress Cheryl. It looks great with these boots :) Thanks for sharing at Creative Mondays.

Jessica Jannenga said...

I am a fan of OTk boots and love your taupe ones, they will go with anything and are a refreshing change from black. Love the embroidered boho vibe of the dress. have fun on your trip!
thanks for linking!
jess xx

Shelbee on the Edge said...

Yes, Cheryl! This is absolutely fabulous! I love all the fun details on this dress. And the otk boots are the perfect footwear to transition the dress for cooler weather. I love wearing my spring dresses with boots and sweaters in winter. Great look, my friend.

Thanks for linking up with me.


Shelbee on the Edge said...

Cheryl, I just wanted to pop in and let you know that this post will be a featured favorite on tomorrow's #SpreadTheKindness Link Up!


stylesplash@live.co.uk said...

Such a pretty dress, I love the embroidery. It looks great with the OTK boots. Thanks for linking up!

Emma xxx

Elegant Duchess Fashion and Lifestyle said...

how was your trip to Miami?

You look adorable, I love the boots! xx


Chloe said...

Wow! Really LOVE this dress! The sleeves are so fun and unique! This outfit looks so good with your OTK boots too! :)

xo, Chloe // https://funinthecloset.com/los-angeles-winter-popjulia-review/

Mary Tait said...

Love this dress, what a great find! And I love all the accessories--they are just perfect!