10 Simple Winter Style Tips

Oh, winter. You have officially arrived with your subzero windchill and grey skies.


Winter can be a tough month for style if you aren't prepared. I have compiled my top 10 simple winter style tips for all the lovely ladies out there who are struggling to leave the house in pieces other than yoga pants and fleece. There is life beyond sweats, and I promise you will be (almost) as comfortable and a million times more confident!

The key is finding a few select items to carry you through, and styling them so they look effortless instead of contrived, streamlined instead of bulky, coordinated instead of matchy-matchy.

I found the perfect vest to match multiple upcoming events- truly a piece so versatile I can wear days in a row and not care who sees. The Ashling Vest reverses from fabulous grey faux fur to a cinched-waist army green.

Here is how I wear it a few different ways:


I paired the fur size of this gorgeous Cupcakes & Cashmere Ashling Vest with a simple white v-neck blouse, grey denim and Sorel wedge high ankle boots. Since winter = no need to actually style my hair on a daily basis, I popped on a pom-pom hat to hide my static-y do. I mimicked the shape of the shirt's collar with a long multi-strand chain necklace and added a hint of hot pink lipstick.

Tip: To keep that pasty skin at bay for all of my pale sisters, combine a pump or two of luminizer with your base makeup. It isn't as obvious as bronzer but gives that healthy glow.

Tip: For winter, you can combine your summer lipstick with a more wintery shade to brighten up for daytime. If you prefer something more subtle, swipe the fuchsia or magenta on your lips and lightly dab off while pressing the lipstick in to create a stain.


Tip: When wearing mid-calf boots, do a large cuff of your pants just over the top of your boots to prevent baggy ankles. This looks a little lumberjack chic, no?

To amp up the formal factor of this outfit, I swapped out the denim for cream wool pants and added multiple strands of pearls. The earrings are massive "door knocker" style in gold and sparkly pavĂ© detail. 

Tip: When selecting faux pearls, don't go for pure white because real pearls aren't stark white. I always pick mine up at thrift stores for a few dollars and layer multiple strands.

Tip: Experiment with different shades of red at each end of the spectrum. I used SMASHBOX lipstick in Mandarin because it is more flattering to my pale, pale skin than a deep red. Red lipstick with a blue undertone is more universally flattering but I still find it too stark of a contrast in the winter months.

Tip: To get rid of hat hair, reverse your part before you put a hat on. Just part your hair on the exact opposite side. After removing your hat, spray the length with hairspray and smooth with the actual hairspray bottle instead of hands to prevent oil transfer. Anchor the opposite side of your part behind your ear, pushing the hair up and forward for additional volume.


Tip: To make your look 100x more put together, add a massive pair of earrings. It looks like you put SO much more effort in than you actually did! I keep a pair of large simple gold hoops in my glove compartment for on-the-go styling.

For a more informal look, I reversed the vest to the military green style and added girlfriend jeans and a grey cable knit sweater paired with leopard slip ons. I added structural gold, jeweled and lucite earrings, and a girly pink lipstick to complement the green in the vest. The mom ponytail is in full effect, but kick it up an inch or two higher than you normally would and rough it up, so it is almost on the crown of your head.

Tip: Pair an animal print shoe with any neutral look to keep it interesting. I have leopard in every style- heels, flats, booties, and sneakers!



This is definitely my "mom-on-the-go" look, complete with a leather backpack for my MacBook Air. I love pairing different shades of the same color together in one look- it adds dimension without getting busy.

Tip: Girlfriend jeans are more feminine (obvi) than boyfriend jeans. They sit higher on the hip and have a straighter, more fitted leg. Still incredibly comfortable but add a more structure to your outfit than boyfriend jeans do.


Tip: When wearing a reversible item, wear the opposite color underneath. For example, this vest is green and the underside is grey, so I paired it with a grey sweater. The material that peeks out will match what you are wearing!

Let's talk about shopping now! I am sure you are wondering where I snagged this adorable vest...

How often do you head into a store, only to find that every dress is too short, every top too revealing, and every item too flimsy to last more than one wash? Or the opposite- the style looks more appropriate for your mom, makes you feel frumpy and utterly shapeless?

Finding a store with that perfect balance- classy yet stylish, on-trend yet not trendy, affordable yet high quality- is a total unicorn. And the bonus: staff that are actual stylists who make you feel like you are shopping your best friend's closet. Welcome to Scout & Molly's in Deerfield!

From the minute I walked into the store, the manager Jackie was ready to assist. Here's the thing- she wasn't pushy, she simply took in my personal style and shopping needs then showed me around the store. She pointed out items that were most popular, styles that might match my frame, and accessories to complete the outfit.

After gushing over my vest, I selected it to add to my collection and spied a few more pieces that I am considering.

Frontier Jumpsuit
Bellwood Jacket
Dreamer Satin Jogger 

The jumpsuit would be incredible for anything from a night out with the girls to a romantic dinner. The Beltwood Jacket actually consists of sequins- a way to add shine and sparkle in a sophisticated way. The camo satin joggers are SO on trend- I would pair these with anything from sneakers and a white t-shirt/sweatshirt to heels and a lacy tank.

Here's the best part: My readers receive 10% off in store when they shop at Scout & Molly's in Deerfield! Simply mention that you heard about them through me and you receive a discount on your entire purchase. They are located in Deerfield Square at 740 Waukegan Rd, alongside Whole Foods, Red Door Spa, Pure Barre and Barnes & Noble. I run all my errands in the square and then treat myself to a style refresh at Scout & Molly's!


Cheers to ringing in 2018 with style, grace, and passion not sweats and indifference!

Disclosure: I received an item of clothing for review purposes; all opinions are honest and my own as always.

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