I find that dresses are the trickiest and most anti-climatic item to buy. Hear me out: the event that warrants buying a dress, and the day-of wearing, is the fun part. Browsing online, plotting with friends, purchasing something new and shiny (the dress itself or the accessories to go with it-or both!), and the event itself is a process I enjoy. I’ve rounded up my  winter dress picks (ever better: the one I’m wearing is under $100 and now comes in 8 colors)!

The anti-climatic part of  purchasing a dress: figuring-out where to wear dress A, B, and C for the second or third time to get your money’s worth out of the dress. My mental checklist to wear a dress after the initial wear: is this event with the same group of people, is the season right, how many pictures are on social media of me wearing it? It sounds ridiculous as I’m writing  this down, but the struggle is real!

| Dress: ASTR the Label | |Shoes: Target | Earrings: Lisi Lerch |

|Fur Coat: Marshalls (sold out, similar linked) | Lip: Bobbi Brown Luxe Lip in Neutral Rose |

Picture Credit: Elizabeth Grant Photography

I wore this red lace dress to a fall wedding:  it was a black-tie optional event so I dress it up with these strappy heels and all-time favorite Lisi Lerch earrings. For a winter wedding, I opted to switch out the nude heels for black strappy heels and added a faux fur stole (try a fun multi-colored option if you’re going for a statement)! A teddy bear jacket is a way to accessorize but keep a winter dress warm on a chillier night.

Let’s get our money’s worth: How to style for spring:

You could easily wear this dress to a semi-formal spring or summer occasion with classic Jack Rogers sandals or these go-with-everything wedges! I bought this dress with the intention of wearing it for the wedding, but knowing I can wear it again in different seasons and to different occasions made the purchase worth it! Even better, we’re talking a under $100 price tag! When I purchased this dress, it was only available in three colors, but now you can get it in this pretty evergreen, plum, and my favorite, navy! If you want to be 100% versatile, stick with the classic black!

I rounded up a few more winter dresses that you can shop above! My theme: rich colors, textures, and classic (timeless!) silhouettes!

What’s your strategy when it comes to buying dresses?