How to Double Your Winter Outfits for Under $30

Maximize your winter outfits!

Despite being Caribbean-born and firmly tropical-blooded, I somehow ended up living with a snow bunny who wants to go out and do things in cold weather. When it’s chilly out, you know that bulking up is not my style, so I needed a creative way to build more winter outfits – and it all started with a wardrobe malfunction at work (eek.)

When 12:30 rolled around, I was already outside on my way to the nearby H&M. Though I’m not a regular customer, I know I can expect to find vigorously search for affordable basics. Thankfully, the universe heard my distress signal and put exactly what I needed near the entrance of the store: a rack of long-sleeved black turtlenecks. For the first time ever, I escaped the giant store in minutes.

I put it on as soon as I was back in the office and three things happened:

  • My outfit looked 10 times better (I did the math)!
  • It made my necklace pop.
  • Most importantly, I was comfortable and could resume projecting confidence without worrying about errant straps.

Keep in mind that I hadn’t worn a turtleneck shirt since sixth grade, when I had one in each color of the traffic light(true story.) By the next week, I had worn all of my staple winter outfits. I was about to settle for the “I-haven’t-washed-my-favorites-yet” sweater/pants combo when I remembered the turtleneck. Of course! It fit perfectly under another dress, and that made two new winter looks with minimal effort.


I had to know how many more winter outfits I could make.

So I threw myself a dress-up party and tried the turtleneck with almost all of my summer dresses, and it was personal style gold. I was already wearing tights under dresses for fall, so this was a seamless addition to that same formula. Extra tip: to keep the layering smooth, tuck the shirt into the tights (I call this the interpretive dance base layer.)

This system is comfortable, chic, and easy to put together for any occasion. Over the last month, I’ve worn it for work, happy hour, and a holiday dinner. At this rate, I’m ordering at least one more shirt, and considering a second color. To prevent your winter style from looking too uniform, switch up the shoes and accessories based on the dress. The easy way to do that is to treat the base layer like a backdrop. Instead of trying to match it or coordinate to it, focus on the dress/skirt as you’d normally wear it and the look will come together. For this post I’m only featuring five winter outfits, but I could have just kept going – can you tell how happy this makes me? I love getting more mileage out of my clothing!

For the weekends:

My weekends are reserved for boyfriend time, cleaning, and writing, so if I’m leaving the apartment, it’s either for casual brunch or fancy brunch. For the casual look, I layered a short cutout dress with a faux leather & fur vest, heattech tights and my OTK boots. For the fancy look, I chose my Altuzarra x Target tuxedo dress. In warmer weather, I normally wear a crepe tank under this to soften the daring dip at the front, so the higher neckline here emphasizes the lapels and throws attention to the beautiful embroidered cranes on the shoulders.

Casual Winter Outfit
Formal Winter Outfit
[show_shopthepost_widget id=”2231764″]

For the office:

I’ve become addicted to these over-the-knee boots and I just want to wear them with everything. I was hesitant to wear them to the office at first, but working in a design office makes it easy to experiment with style. I may need to feature some of my coworkers on here soon, the fashion world isn’t the only place where office dressing isn’t boring!

Neutral winter outfit for work
Colorful winter outfit for work
[show_shopthepost_widget id=”2231755″]

Party Time!

This outfit is my favorite so far! I chose a neutral grey dress and enhanced it with jewelry & a pop of color in my accessories. The statement necklace brings in just the right amount of glitz (for me), and being able to wear (flat) purple booties is always a win!

[show_shopthepost_widget id=”2231763″]

What do you think?

  • Would you try this look out?
  • How do you layer up for the winter months?

Full Gallery

P.S. This post contains affiliate links to similar styles of what I’m wearing. I tried my best to recreate the looks, but most of what I wore is sold out! If you’re interested in a particular piece, feel free to tweet me!