Off the Shoulder Dress + Over the Knee Boots

Off the Shoulder Dress + Over the Knee Boots in Boston, Massachusetts

Since New England’s style is so casual, sometimes it just feels SO easy to throw on a t-shirt, oversized sweatshirt, leggings, and go on the weekends; Especially in cold weather! If you haven’t been to New England in the winter, you don’t understand how casual it can really get. Style almost completely goes out the window once it gets to the temps where you can’t feel your face. But, it is totally possible to stay warm while also looking cute and put together!

Off the Shoulder Dress + Over the Knee Boots

Some of my inspiration for this outfit from a look that was recently seen on Gigi Hadid. I’ve been completely obsessed with her since a few years ago when she made small appearances on Real Housewives. Gorgeous, genuine, and killer style. I could go on forever about why I love her but I will stop. One thing I love about Gigi’s style is how effortless and wearable it is for the everyday girl. I have paired an off the shoulder sweater dress with over the knee boots. This off the shoulder sweater dress is obviously not quite as oversized as Gigi’s, but makes it feel more wearable for a non-celebrity on date night (I swear they are so lucky that they can get away with wearing pretty much anything).

I have been obsessing over Stuart Weitzman’s suede over the knee boots for years now, but I just haven’t been able to pull the trigger because of the $700-800 price tag. It got bad you guys …. to the point of obsession where I was (okay still am) checking Tradesy, E-bay, PoshMark, Vestiaire Collective… everything…. every single day for like a year LOL. I still haven’t completely given up (still saving those pennies), but fortunately, there is another option for those of us who can’t get enough of over the knee boots.

In the fall I purchased Ivanka Trump’s over the knee boots and they have surprisingly held up pretty well for the price. I recently purchased these over the knee boots and I’m obsessed. They are faux-fur lined in the foot area with a heel that’s the perfect height whether you’re dressing for the daytime with jeans and a t-shirt or date night for a sexier outfit. They tie in a bow in the back just like the Stuart Weitzman boots. Although I do still love my Ivanka Trump boots (similar), these are much better quality.

I wore this monochrome look for date night followed by drinks in the Old Port in Portland, Maine at Fore Street and Central Provisions (go immediately to both if you haven’t been) and recreated it in Boston. For colder weather when I was in Portland, I wore leggings underneath for a warmer, more toned down feel to the outfit. What are your tips and tricks for staying stylish in cold weather? I would love to hear! xx