New Year is starting off right!

December was a crazy month for me! Hell, even November was, but that was because I took a 10 day staycation to Indianapolis. Super Fun! But then I was unexpectedly home for 2 weeks in Indiana with family.

Since this took a toll on my social life, I feel like I have lost time to make up for. Good thing I have 3 dates scheduled this week! Can’t wait to blog about them later this week!

In the meantime I am semi-stressing about what to wear as the weather we are having in Chicago is crazy! Normally, I would be in skinny jeans and a cute top, but with all the snow all I can think about wearing is sweatpants and Uggs. Along with no judgement from my date.

This made me think I am sure others in such wintery areas have the same dilemma. I always feel my cutest in some high heels, but that will not be happening this week. Listed below are a few outfits I would totally wear for a first date.

dressy casual 2 I love grey! I love that this olive top is a bit flirty yet the sweater brings it in the make it more cozy. Not a huge fan of the style of boot it is, but pairing it with a similar grey boot or even black I think would totally work. Of course completing the outfit with a cute scarf and earrings would be my choice.

dressy casual 4 Love the loafers! I also just love the simplicity of this outfit. Cute jeans, cute sweater- done and done.

dressy casual 3Love the red! I am a true believer that red is a power color. I think it just makes you feel more confident and after all we all probably need that on a first date! I am digging the cardigan as well, but I must warn you, be careful of flowy open cardigans. They can make you look frumpy if they are just too open. I normally by mine a size smaller to get the appropriate effect.

dressy casualThis is totally my winter style. I love a good simple tank or tee-shirt to go under a cardigan or sweater. I think a great bold necklace always make any outfit look dressier than what it is. Loving these tall boots, but they could still be a challenge to walk in when it is icy and snowy.

blazer Lastly, I feel like  you can never go wrong with a blazer. I am also a HUGE fan of color blocking, when it done correctly. The only changes I would make for this outfit would be to wear a more neutral shoe (black or nude) and bring a neutral handbag. Too much color blocking can make you, in my opinion, look like you are either 12 or a drag queen. Neither are flattering when  you are trying to make a decent impression on a first date.

Enjoy my style, and if you have any suggestion on what you would wear on a first date, I would love to hear them!

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