Winter Outfit Inspo

January 8, 2019

Maison Scotch Coat I Winter Outfit Inspo I Meghan Donovan

We’ve officially reached that time of year where getting dressed is rough. I find myself struggling to pull together outfits and need to look through my archives in order to get dressed in the morning. (It does not help that I’m also on a self-imposed shopping freeze!) We have several months of winter still ahead. So I thought I’d share some winter outfits from years past to give you some inspo when it comes to outfit arranging particularly now that we’re all back to work and having to put aside the leggings/sweaters all day, err day that I know prevails around the holidays. (Tell me it’s not me!)

Winter Outfit Inspo

Cute Winter Outfit Inspo I wit & whimsy

A faux shearling coat, corresponding colored knit, cozy beanie, skinny jeans + suede booties.

Preppy Sweater Dress Winter Outfit Inspo

A sweater dress + over the knee boots (similar for less here, too).

Plaid Coat and Booties Winter Outfit Inspo

A plaid coat with a chunky turtleneck and black skinny jeans and black heeled booties.

Meghan Donovan of wit & whimsy discusses affordable wardrobe essentials

An oversized blazer (similar here, here), distressed jeans (on sale) and black pointed toe flats.

Neutral Winter Outfit Inspo

A black and gray monochromatic look of a waffle knit sweater, gray jeans, over the knee boots and a chic black coat with an oversized collar.

All Black Look with Pop of Red

A dressier date night look of a cashmere sweater (less expensive one here and one here) and lace pants and black pumps.

Gray and Black Winter Layers

Lots of layers with a knit sweater over a plaid button down, gray jeans and black heeled over the knee boots. Top it off with a gray coat + black cashmere scarf.

Styling Faux Leather Leggings Winter Outfit Inspo

Leather leggings (on sale) with contrasting white pumps and a bomber jacket.

Styling a Duster I wit & whimsy

A duster cardigan (more here, here) paired with a plain white tee, dark wash jeans and heeled booties.

Camel Coat Winter Outfit Inspo

Go sporty spice by pairing sneakers with distressed jeans and a cozy cableknit.

Boyfriend Jeans + Pumps Winter Outfit Inspo

Pair boyfriend jeans with a striped tee (size up in this tee!) and classic black pumps. Top off the casual meets chic look with a beanie.

Vince Leather Jacket I wit & whimsy I Meghan Donovan

Make shorts work year round by layering them over tights and adding a cashmere sweater and leather jacket with heeled booties.

Meghan Donovan styles Everlane's puffer jacket

Make your practical winter wear like Bean Boots and puffer jackets a bit more stylish by adding a monochromatic sweater and fringed scarf.

Styling a cape I Winter Outfit Inspo

Switch up your outerwear by adding a cape into your rotation.

Teddy Coat and Kick Flares on Meghan Donovan

Go cozy and stylish by leveling up a teddy bear coat. Other chic teddy bear coats here, here and here.

Day in the life I wit & whimsy

Layer a striped tee under your favorite chunky knit sweater and pair with cropped jeans and suede booties.

Fall to Winter Travel Outfit I wit & whimsy

Pair an oversized sweater with velvet or leather leggings and a chic pair of sneakers.

Fall Outfit on wit & whimsy blogger Meghan Donovan

Dress up with a knit skirt, a cashmere sweater (less expensive one here) and a pair of suede heeled booties and a cute striped scarf.

Winter Neutrals on Meghan Donovan of wit & whimsy

Go for winter neutrals by pairing your favorite white jeans with a cream sweater and camel coat (another great one here.)

Winter Work Wear Outfit Inspo I wit & whimsy

Layer a silk button down with a sweater and top it off with a cool moto jacket.

J.McLaughlin Sweater Jacket

Pair a festive red sweater with a sweater jacket or coatigan for warmth and layer over faux leather leggings.

. . .

Hope this helps you guys as you get up, get dressed and get out the door! Do you have a favorite look from the above? Would love to hear!

p.s. leathering leggings four ways and a look back on 2018.

[Bekka Palmer and Carter Fish Photography]

comments +

  1. Shirley says:

    Thanks for all of the inspiration! I find this time of year to be challenging for dressing as well and this post is perfect!

  2. Yana says:

    Great post this morning! Love getting ideas (especially for winter) and all of your outfits are gorgeous!

  3. Kate Scott says:

    So many great ones, bookmarking this for the next four months!!

  4. Nancy says:

    See what a positive the shopping freeze can be? Its great to go “shopping” in our own closet every once in awhile. Preferably with the fresh eyes of a good friend (or Amy in my case) and pull out some old favorites we had forgotten about. You look lovely in all of these pulled together looks. Thx for the inspiration Meghan.
    Happy New Year. xo

  5. Libby says:

    OMG this helps so much! Every outfit I tried on this morning, and looked at in the mirror, I would say “too christmasy”, and take it off. This cycle happened multiple times, and was actually quite comical! ahahaha

    xoxo Libby

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