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


  • Reply Steph February 12, 2019 at 10:37 am

    Ths is such a great piece. I love the back V, I also love dark florals for winter!

    • Reply Tilden February 12, 2019 at 5:04 pm

      Thank you Steph! Dark florals for winter are my fave to incorporate too! xx

  • Reply Marta February 12, 2019 at 10:46 am

    Confession: I’ve never tried any of the styles you mentioned, including the lbd… but the good news is I’m trying to change my style a bit and I’m definitely gonna take your post into consideration next time I go shopping. The dresses you linked are absolutely gorgeous, the lace ones are my favourites though.

    • Reply Tilden February 12, 2019 at 5:03 pm

      YOU GO GIRL!! Changing & trying new styles can be so daunting but I applaud you for it! I can guarantee any of these dresses would be fantastic to try out. Can’t go wrong with wrap front &/or lace xx

  • Reply Jordan Nelson February 12, 2019 at 1:22 pm

    Wrap front dresses are a fave of mine. They accentuate all the curves I want them too haha

    • Reply Tilden February 12, 2019 at 5:01 pm

      They’re my favorite too! So chic & sophisticated in all the right places! xx

  • Reply Lex Clouthier February 12, 2019 at 2:36 pm

    This piece is so classic! Love it!

    • Reply Tilden February 12, 2019 at 5:00 pm

      Thank you Lex!! xx

  • Reply Maureen February 12, 2019 at 3:56 pm

    These are all classics! I love a good floral dress any time of the year. Your black dress is beautiful and so timeless. Love the v-back and your handbag is icing on the cake! So cute!

    Maureen | http://www.littlemisscasual.com

    • Reply Tilden February 12, 2019 at 5:00 pm

      Thank you so much Maureen!! xx

  • Reply Alicia February 12, 2019 at 4:49 pm

    You make this look so effortless & chic! The simplicity of the LBD lets your gorgeous necklace & the sassy reg gingham bag POP! All around so beautiful! xo

    • Reply Tilden February 12, 2019 at 5:00 pm

      Thank you so much Alicia!! You’re so sweet xx

  • Reply Jessica A Jannenga February 17, 2019 at 11:27 am

    This is so sleek and stylish on you! I love the dress with the black booties. I have been looking for more midi dresses myself.
    thanks for linking!
    jess xx

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