Under $100 Winter Dresses To Wear Into Spring

Mid-Length, Signature Black.

You really can’t go wrong with a LBD to wear during any of the four seasons. But provided winter and most of spring is relatively chilly, a mid-length dress is a great option to wear. When I saw this particular black one I’m wearing above, I loved it for all the dressier occasions I could wear it to during the winter. It feels like a nicer t-shirt dress in fabric, but accentuates my waist with a built-in fabric belt which is so clutch! The slit makes it easy to wear & all around adds to this sophisticated option you can wear from the office to dinner.

Dark Florals With Sleeves.

Florals aren’t just for spring-time merriment. In fact, I love wearing them during the winter because I feel like they cheer up the moody city lol. With the addition of a sleeve and a darker choice of color, you can comfortably wear the print during the winter without fear of stares. But TBH if anyone stares at you, they’re probably just jealous of your happiness & you don’t need to associate with humans like that anyway.

Structured Lace.

I LOVE wearing lace & just because it’s cold out, that doesn’t mean you can’t incorporate it. All you have to do is go for higher necklines & longer hemlines to make it work. There’s seriously nothing sexier than a structured lace dress, especially for date night. Just pair with sheer tights and heeled booties that make you feel like the powerful boss lady you are.


This particular style has become a favorite of mine, as I find it fits my body better than most others I’ve previously owned. When I found this stunning red one while browsing for Valentine’s Day dresses, I really adored how it fit in all the right places while not suffocating me in the process. Plus, I can totally wear something this bright into spring & definitely into the summer. In the meantime, I’ll pair it with my favorite pair of sheer tights to “winterize” it.


Dress: ASOS (wearing US 6) | Coat: ASOS | Booties: Coach (old, similar here) | Bag: Neely & Chloe

Earrings: ThePeachBox (use code ‘tobebright’ for 15% off) | Necklace: Sequin