4 Winter Outfits You Can Wear to Make it Through the Winter + FREE 7-Day Winter Outfit Guide

I’m sorry to tell you that winter is still here. 😩😂 If you’ve been feeling the grind and need a little inspiration or spark to help you get through it, here are 4 winter outfits that you can copy!

These outfits are from the Winter Wardrobe Guide that is available in the PMT Style Club. Each month, members receive a booklet of outfit prompts to help them plan what to wear.

You can get a small taste of the guide by downloading my FREE 7-Day Winter Wardrobe Guide. It actually has 15 outfits that you can pick and choose from to help you get dressed this week, including casual, work, athleisure and date night outfits. This guide has you covered!

And, if you want to jump into the PMT Style Club for spring, it’s opening again on March 1st! Come get a fresh start with your wardrobe! We’re starting the season off with a closet clean out challenge (!!), a spring wardrobe workshop, and all of the usual style masterclasses with professional stylists, Q&A sessions where you can ask me all of your style questions, the Spring Wardrobe Guide, and more! Learn all about the PMT Style Club HERE and sign up on March 1st!

Until then, here are four outfits from the guide that you can copy to help you through the winter slog!

SIZING: I’m 5’6″ and usually S/M or 6 in clothes and 8.5 to 9 in shoes.


Nice Outfit: white balloon sleeve sweater + black flare pants + cognac booties + gold pendant necklace

1. Work
One way to make “boring” black and white less boring is by playing with silhouettes. I recommend having one pair of standard black pants for work, and another pair in an alternative silhouette to change things up.

So, find a pair of alternative black pants (or whatever your preferred neutral is), and wear it! When you pair it with tops you would normally wear with more standard pants, it will give your outfits a fresher feel.

These pants are STRETCHY and really comfortable, but they look very polished, professional, and dressy. And, they just make a bit more of a statement than standard black pants, without being overpowering. You can wear them in a work look like I’m doing here, and you can dress them up for a special occasion, like I’ve shown in the past, HERE.

These pants are available in both black and navy, in sizes 00 to 20, and in regular, tall, and petite lengths. Lots of options that you can see HERE. I wear size 6.

To add one more element to create visual interest, I added cognac to the mix instead of black shoes. I like how the cognac softens it up a bit! You can find the boots HERE. I wear size 9.

Shop the Outfit:
Sweater: Nordstrom (exact—wearing size S; similar)
Pants: Gap (exact—wearing size 6)
Booties: Amazon (exact—wearing size 9)
Necklace: c/o Dear Mushka (exact)


Casual Outfit: tan striped long sleeve tee + tan sherpa fleece zip-up jacket + medium wash straight leg jeans + taupe sneaker booties

2. Casual / Weekend
This is an easy casual outfit to copy: Wear a printed tee of some sort, then wear a casual layer that’s in the same color as one of the colors in your print. That’s called “color pulling,” and it helps your outfits to look cohesive.

I love zip-up fleeces or sherpa jackets as cozy, casual layers in the winter that keep you warm! You can of course wear a cardigan, but jackets like this are so much warmer. This particular jacket is mostly sold out, since it’s the end of the season.  But in case you can find it in your size, it’s really lightweight but thick and cozy. Find it HERE. I wear size XS as it runs pretty large.

This tee was sold out for a bit, but it appears to be available in a few sizes. And it’s on super sale! Find it HERE. I’m wearing size M as I sized up for a bit of a looser fit.

Shop the Outfits:
Striped Tee: Kohl’s (exact—wearing size M)
Fleece Jacket: Kohl’s (exact—wearing size XS, runs large; similar)
Jeans: Nordstrom (similar—I wear size 6)

Sneaker Booties: Nordstrom (similar)

Necklace: Nordstrom (exact; super similar)


Dressy Casual Outfit: green puff sleeve sweater + black skinny jeans + black lug sole boots + gold pendant necklace

3. Nicer Casual 
If you’re looking to stay casual but step it up just a bit, go for something like a sweater with special details and well-fitting black or dark wash jeans. The special details will elevate the look and dress it up a bit without being dressy.

Shop the Outfit:
Sweater: Nordstrom Rack (similar, similar)
Jeans: Liverpool Los Angeles (similar, similar—I wear size 4)
Boots: Nordstrom (exact—wearing size 8.5)
Necklace: Nordstrom (exact; super similar)


Nicer Date Going Out Outfit: black and white polka dot blouse + black leather jacket + cognac corduroy pants + black suede booties + gold initial pendant necklace Nicer Date Outfit: black and white polka dot blouse + black blazer + cognac corduroy pants + black suede booties + gold initial pendant necklace

4. Date or Going Out
If you’re headed out to dinner, try a blouse with a moto jacket or a blazer! I personally love moto jackets, but if a blazer is more your style, do it! Both options totally polish up outfits.

This is a blouse that I reviewed a few weeks ago and also showed in the recent post “7 Outfits With Bootcut Jeans for Winter”. Here it is again but with brown corduroys this time! I love how corduroys add some texture and dimension to the outfit. But, this outfits works just as well with dark wash blue jeans or black bottoms. It’s totally up to your preference.

The blouse is available in 2 solid colors and 5 prints and in sizes XXS to 5X. Check it out, HERE. I wear size S.

Finish it off with pointed toe shoes. Pointed toes will sharpen up the look and add another element of polish which is great for a date outfit. These booties have a high and narrow shaft that works nicely under different types of straight leg pants. Find them HERE. I’m wearing size 9.

Shop the Outfit:
Top: Amazon (exact—wearing size S)
Moto Jacket: JCPenney (similar, similar)
Blazer: Nordstrom (similar, similar)
Corduroys: Gap (exact—wearing size 6/28; similar, similar)
Booties: Gap (exact—wearing size 9)
Necklace: Nordstrom (exact; super similar)

Those are some outfits that you can try and some tips for pulling them off with pieces in your own wardrobe!

If you want a booklet of 15 outfits to help you push through the rest of winter, download my FREE 7-Day Winter Wardrobe Guide by clicking that link and entering your info!

And, if you’d like my help with your style this spring, join the PMT Style Club when it opens again on March 1st! Join us for the closet clean out, spring wardrobe planning, all of the great masterclasses, and more! (The members LOVEDDDDDDDD one of our recent masterclasses with a top-tier image consultant who helped us identify our best colors!)


Closet Clean Out Challenge + Spring Wardrobe Workshop and More – Opens March 1st!

If you’re ready to get out of the winter funk and step up your style this spring, join us in the PMT Style Club when it opens on March 1st!

The PMT Style Club is a seasonal style membership that combines wardrobe strategy and done-for-you resources with style lessons, personalized tips, and the power of community. You’ll find motivation, practical style help, and the support you need to feel your best everyday.

You’ll get access to style Q&As with me, wardrobe guides, outfit prompts for an entire season, style courses, and masterclasses with professional stylists, and get to connect with other women who won’t think you’re weird for loving a good outfit, plus you’ll have a place to ask all of your style questions.

Get the help that you need to get unstuck and love your style again!

CLICK HERE to join the waiting list to get notified when it opens and join us!

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