Fall is definitely my favourite season to dress for. Boots, sweaters, and pretty knits are back, and we can start wearing jeans again without feeling too hot. My work wardrobe is usually business formal, so I like to try out new styles on my down time. I decided it was time to update my closet with pieces that can work for dinner, casual Friday at work, and even date night. Here are a few of my favourite tried and tested fall date outfits.

 Casual Coffee Date


Sweater and Pants, J Crew. Booties, Target. Watch, Michael Kors. Bag, Danier

For a coffee shop date, you want something cute but casual. The pants are basic khaki’s and the sweater is very light and soft, so you can sit back and chat without feeling too stuffy or restricted. Adding booties makes an otherwise plain outfit seem more hip and on point.

Outdoor Activity


Jeans, Calvin Klein. Sweater, Old Navy. Jacket, The Bay (old). Scarf, Express (old). Boots, Nordstrom. Bag, Rebecca Minkoff

Pumpkin Patches, Thanksgiving Parades, Santa Clause Parades, and Winter Fests are great dates but hard to dress for. The key is to layer your pieces. In this outfit I have a tank top on under my sweater, and once I add my coat, I will be toasty warm. Remember to bring a scarf and mittens, and wear a crossbody bag to keep your hands free to hold a cup of cocoa, hot apple cider, or your sweetie’s hand.

 Dinner and a Movie


Jeans, Calvin Klein. Sweater, Ann Taylor Outlet. Boots, Marc Fisher from Macy’s. Purse, Alexander Wang.

 On Dinner and a movie night, I like to dress up a bit but still stay on the casual side. You might only be going for pizza and a movie but it is date night after all and I like dressing for the occasion. This outfit is pretty but still laid back. The embellished top makes it a bit fancier, but with jeans it keeps the look just casual enough. Add some sexy tall boots and a knockout bag and you’ve got a great date night outfit.

 Fancy Date Night


Skirt, H&M (old). Denim Shirt, J Crew. Booties, Winners. Clutch, Louis Vuitton.

 For a fancy night out, you can really shine.  This outfit is one of my favourite looks. The summer skirt is transitioned to the colder weather with the addition of tights. By adding a denim shirt, it takes the look from sexy to funky. The important thing to remember here is footwear and accessories. I went with black booties but I’ve also worn this look with pink shoes that match the skirt. For jewelry, I’ve added a sparkly necklace from Jewel Mint. I like a pop of sparkle against the denim because it feels more luxurious and less lumberjack. This outfit is pretty, and comfy.

I like to be comfortable on dates and not fiddling with my outfits. No matter where you are or who you are with, discomfort shows and you won’t be able to fully enjoy yourself if you’re picking a wedgie or trying to pull down a too-short top. I hope my outfits have given you a few ideas for cold weather outfits. Do you have a must have Fall piece? Is there an item in your wardrobe that makes you feel like a million bucks when you put it on? Leave a comment below and let us know.

Written by Cat