I know we don’t have many reasons to get dressed up these days, but I do know I’ve been in a handful of situations where I needed to change out of my 24/7 leggings and put on something I didn’t wear to bed the night before. Otherwise known as anything that makes you look presentable to wear to dinner at your (soon-to-be) In-Law’s place – you get the idea, something purposeful & intentional.

Normally I’m someone who plans outfits out in advance for dinners or any occasion on the calendar that calls for leaving the house. Although I stick to the casual/comfy side 95% of the time, there are moments where I’d rather not wear my go-to pair of white sneakers, especially in the winter months.

So that’s where this classic fall/winter, tried & true, dressy-meets-casual outfit idea comes to my last minute rescue whenever I need to throw something on that looks like I spent more than 5 minutes putting together. An oversized mock/turtleneck sweater, skinny jeans with an over-the-knee boot, and a lil’ hair accessory is all it takes to dress up an otherwise very casual look I’d choose to wear during the day (if not leggings/sweats.)

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A mock or turtleneck sweater is a great choice of top for the winter, especially one that’s slightly oversized to fit like a tunic. I personally gravitate towards this style in the winter because not only does it appear more sophisticated than other necklines, but it also helps to keep your neck warm if leaving the house sans scarf (although it looks great with a scarf draped around the shoulders too!) I’m also a big fan of oversized anything because it allows me to hide underneath it, especially after a big meal. I can’t tell you how many times I’ve unbuttoned my jeans and hid the fact I did under my sweater 😀

Tip: Even if the sweater doesn’t run oversized, buy it in 2 sizes larger than your normal if you know you’ll enjoy it more knowing it will go past your waist (or past any point on your body where you feel most comfortable.) Often times sizing up this way on an item that is meant to be more fitted looks much nicer on than something intentionally bulky/oversized. Less fabric to have to work with, but just my opinion.

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A great trick to hiding unwashed hair or to avoid the need to style it last minute is by pulling it back & adding a hair accessory. I’ve been wearing children’s hair bows for more than a year now and I find it so much fun, especially on a seasonal level! My good friend Elise founded The American Weekend Society brand and makes the cutest hair bows with the best fabric (all of which are hers shown above.) I always get so excited whenever she launches a new collection because I know her fabrics are SO GOOD. Also my dream is to hold onto all these bows (not all pictured btw haha) and save them for my (hopeful) future daughter to wear when the time comes.

OUTFIT DETAILS

Sweater | Denim | OTK Boots | Hair Bow

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Last thing I’ll mention about this look is the choice of OTK boot over an ankle bootie. I honestly love how this style of boot instantly elongates the outfit appearance, which is very flattering especially with an oversized sweater such as this one. I’m more of a fan of flat boots (fave pair here, so worth the investment) but I like the heel option on this pair because it’s a wide block & still comfortable to wear even after several hours.