When I buy an item of clothing, I try to imagine how I would wear it year-round. I like to invest in pieces that I know will be used a lot. I find it easy to transition from summer to fall and then to winter with only a few changes to the outfit! I especially like to buy dresses year-round and I luck out because I feel like there is more of a selection of dresses in the colder months.

I recently bought this floral dress and I love that it’s darker because it is perfect for fall. I love wearing bright colors in the fall, but I loved that I was able to find a floral dress that wasn’t bright and cheery because I rarely see ones that feature darker colors. However, I bought this to wear in the summer and summer’s days are becoming quite numbered. I then decided to plan outfits for fall and winter so that I can still wear my new dress. Below, I’ll show you I plan on wearing my dress for each season.

Here in Washington, our summer weather typically lasts from July to September so we have another month of warm weather left. I bought this dress a few weeks ago and plan on wearing it through the rest of September since it will still be warm out. In the summer, I dress very simply and with as few layers as possible. I also rarely wear jewelry during the day because I feel like it weighs me down when it’s so hot outside. A typical way I’d wear this dress in the summer is with sandals and only an accessory or two. Above, I paired this dress with brown sandals and a brown belt. It will take two minutes to put this outfit together and everything ends up matching and fitted. It will also keep you cool in the hot summer heat.

I find it pretty easy to transition into fall. I usually throw on a pair of tights and a cardigan and a few more accessories and call it good. I then add boots or flats to the outfit. Since I live in Washington, I usually stick with boots because of how much is rains in the fall. They keep my feet dry and warm. For today, I added black tights and black riding boots to keep my legs warm. I then just added this green cardigan for when it starts to get colder. Finally, I  added these long necklaces for accessories and I am ready to wear this outfit in the fall!

The fall to winter transition isn’t as drastic as the summer to fall one, but as the weather starts getting colder, I have to put on more and more layers. I personally love trenchcoat style jackets–they’re all I own. A great way to winterize this outfit is to simply add a trenchcoat. I added this green one to give my outfit a pop of color. Now, I can wear this outfit out in those cold winter days and stay warm!

How do you wear pieces of clothing year-round? I would like to hear some of your methods! 

Cheyenne Headrick is a Style & Beauty Editor at Chic Galleria. She is a recent graduate of the University of Washington with a degree in English. She likes interior design, watching comedies, and reading. You can follow her on twitter at @cnheadrick.

Tags: belts, boots, dress, necklaces, style, sweaters, what to wear wednesday