30 Winter Outfits

We’re heading into the first weekend of 2018!  I’m feeling pretty good about the start to the new year, how about you?  If you need a little nudge into the new year check out my 30 Healthy Habits and a fresh way to start your day.  I just started doing this in December and I’m hooked on it!

Today’s post took forever to put together, so I hope you like it!  I rounded up over 30 winter outfits to inspire your cold weather wardrobe! But, instead of just linking everything, I took the time to call out my special pieces that I recommend with fit and style tips.  And I highlighted the sales because so many things are marked WAY down now!

My goal for my blog has always been to share my real life with you, and to energize and inspire you in your own life and that means with fashion too!  I’ve always felt uncomfortable if a post came off like, “hey, look at what I’m wearing today” as opposed to being more helpful.  Does that make sense? That’s also why I’m starting to combine fashion and productivity posts together.  I figure it’s the best of both worlds in that way!

30 Cute Winter Outfits


THE LEGGING ANKLE JEANS : If you’re lucky, you can find the sale ones in your size, but snatch them up quick. I feel like every time I look at these jeans (which is often), they’re available in a different size. Here’s the link to the full price version #wompwomp. If I’ve said it once, I’ve said it a million times – these are the best jeans. I don’t often recommend designer brand jeans – they’re so expensive! – but dang, are these worth it!  I don’t know how they do it, but they make you look so super skinny and they make your legs look so long!  Both of which are miracles for me at 5’1 with bigger thighs for my size.  No wonder nearly 300 women gave them rave reviews!  Mine are a 25, they fit TTS and hold their shape all day long (no sagging booty)!! ?

BOOTCUT JEANS : It’s not easy to make a 5’1 girl look tall, but even I look leggy in these jeans!  I will say they stretch with wear, so size down.  I’m wearing 0P and the length is fine on me with a heel. They have a lot of stretch, which makes them ultra comfy, but also looser throughout the day. With a bootcut jean, you can really accentuate your shape by tucking in your top and adding closed-toe heels to make those legs look they go on forever.  A pointy toe adds even more length. This is also the same brand of my fave budget skinny jeans!
BUDGET FRIENDLY RIPPED SKINNY JEANS : I’ve come to rely on Articles of Society as a great budget-friendly brand of jeans.  They’re typically a little thinner than a designer jean and have a lot of stretch, but they are always super comfortable!  You can size down if you’re between sizes. I usually wear 25, my true size.

STRETCH SKINNY JEANS : For a darker, more dressed up skinny jean, I’m smitten with this pair that has a light whiskered finish for an extra cool vibe. They are mid rise, skinny style but not like a jegging, more like a true jean. They are under $100 and fit TTS, with petite sizing too!

Aqua Patagonia pullover

Fleece Pullover S • The Legging Ankle Jeans 33% Off • Boots • Hobo Bag

This fleece comes in 7 colors and it’s super warm. I’m usually an XS in tops, but in this pullover, I preferred the Small for a little bit of roominess.

Fall fashion inspiration - knee high boots with jeans and cozy cardigan, plaid scarf, white top #fallfashion #boots #plaid #scarf

Snuggly Cardi XXS 35% Off •  Boatneck Top XSP •  Budget Skinny Jeans 0P •  Knee High Boot • Similar Link Necklace 40% Off •  Earrings • Similar Plaid Scarf Under $15 • Aviators • Reversible Tote • Wrap Bracelet 

This amazing cardigan is still on sale for UNDER $30 and in this cream color and black. It’s warm and snuggly and long enough to add that extra level of cozy. This particular scarf, one of my faves, is no longer in stock, but I linked one that is very similar and very on sale! It’s got the look of a good plaid blanket scarf with the convenience of being an infinity scarf!!

Red plaid shirt with jeans and black vest black boots

Plaid Top • The Legging Skinny Jeans  33% Off • Boots 50% Off • Similar Vest 33% Off

The highlight of this outfit for me is for sure the $85 boots. If you’re the type that doesn’t want to commit to a major boot purchase in the fall months – now is the time to do it!!

black jeans cognac booties

Similar Tunic 33% Off • Black Jeans 24 (size down)  • Tote • Scarf $6

This scarf is currently $6. Yes, $6. The other colors are also marked down. It’s a great addition to your scarf collection!!

Fall Outfit Inspiration - burgundy sweater, jeans, boots and a plaid scarf #fallfashion

Sweater S • Jeans TTS • Scarf •  Boots • Tote  • Aviators

Barrington Bag (1)

Fleece Vest • V-Neck Top • Budget Skinny Jeans 0P • Slip On Sneakers •  Savannah Zippered Tote • 5 Strand Necklace

Striped Sweater Skinny Jeans and Booties

Sweater XS • The Legging Ankle Jeans • Booties 50% OffBar Necklace • Hobo Bag

I love these booties! You’ll see them again throughout this post. They’re half off, making them under $75, plus they come with multiple color options.

cold shoulder sweater

Sweater 60% Off • The Legging Ankle Jeans  • Booties • Necklace • Tote • Similar Plaid Scarf Under $15

Fall fashion inspiration - long linen blend cardigan, bootcut jeans, plaid scarf #fallfashion #ootd #cardigan

Stretch Bootleg Jeans 0P • Polka Dot Cami (solid cami) US2 • Long Cardigan XSP • Heels ⋅ Reversible Tote ⋅ Aviators ⋅ Y Necklace ⋅ Bar Necklace

Butter Soft Top • Suede Moto Jacket •  High Waist Jeans •  Bag •  Tassel Necklace • Coin Hoop Earrings • Boots

Fall Outfit Inspiration - pink puffer jacket, dark wash jeans with tunic #fallfashion #thanksgivingoutfit #tunic

Similar Tunic XS •  Booties 50% Off • Jacket XS • Stretch Skinny Jeans 0P under $100 ⋅ Reversible Tote under $50  • Similar Scarf • Similar Insulated Jacket 50% Off

Fall Outfit Idea - grey skinny jeans with cardigan and red plaid scarf #fallfashion #thanksgivingoutfit #greyjeans

Grey Skinny Jeans 0 $25 • White Tee XXS • Soft Cardigan XS • Booties 50% Off • Necklace • Similar Plaid Scarf 50% Off • Similar Bag • Aviators

BUDGET FRIENDLY GREY JEANS : Now here are the AMAZING grey jeans!  I honestly feel bad for thinking poorly of Old Navy after trying on this pair and LOVING them!  They are a comfortable mid-rise jean that actually fit me everywhere- the thighs, waist and hips without any gaping in the back.  That’s hard to come by!  Of course they are a little long in 0Regular, but online they also come in short and tall.  (I’m gonna just carefully cut mine with scissors and leave the hem with a raw edge). The quality is nice too- not too thin or scratchy! And like I said, only $15 ($25 if they’re not on sale)! You cannot beat that!


STRETCH CORDUROY SKINNY PANTS : These pants fit TTS and come in both regular and petite (so no alterations needed!).  Whenever Fall comes around, they are one of the first pair of pants I reach for, such a nice change from your everyday jeans! The exact white that I have isn’t available at the moment, but the light tan is actually quite lighter in person. There are, however,  TEN color options and they’re all 50% off!!  

SUPER SKINNY WHITE JEANS : This is the white version of my fave skinny ankle jeans! What makes this pair so special is the thicker fabric and cut.  I tried on so many pair of white jeans and most of them were too thin and too much like jeggings/leggings and made my legs look bumpy and terrible.  Also, they are a mid-rise, so your waistband isn’t in your crotch!  At 5’1 and 105 pounds, I got the size 25 and then had the length taken up and nipped in the waist just a tad. The only drawback to white jeans is that they’re white #duh!, so you just have to make a little extra effort to be careful around food and toddlers (AKA my life).

Fall fashion - gingham top with puffer vest and boots #fallfashion #outfitidea

Shirt 40% OffVest XS Under $15 • Hat • Skinny Corduroy Pants TTS, 0P 50% OffBoots

owl sweater with gingham top and white cords

Sweater • Shirt 40% OffSkinny Corduroy Pants TTS, 0P 50% OffSimilar Heels • Tote

Sweater • White Jeans • Bag • Heels • Earrings • Sunglasses • Jacket


SKINNY CARGOS: When you don’t feel like wearing jeans, cargos are your answer! They’re super comfy and stretchy and fit perfectly everywhere- and no gaping in the waist, so no alterations needed!  You can dress them up or down and I promise they will become one of your wardrobe staples.  With the 0P, I can wear them cuffed for a little ankle peeking out, or down without hemming.  I wear mine mostly with casual outfits and pair them with tees/cardigans and sweaters.  The good thing about this olive color is that it’s a neutral that looks great with any color!

Fall fashion - cardigan with cargo pants and slip on sneakers #fallfashion #outfitidea

TeeSkinny Cargos 0P • Cardi 35% OffTassel Necklace • Aviators • Bag • Shoes


ULTRA COMFY LEGGINGS : Who doesn’t love throwing on leggings and a long sweater and boots in the winter?! These are my very favorite pair that I highly recommend!  They’re the best I’ve found for comfort, quality and fit- being perfectly opaque, washing well, and holding up for years!  They fit TTS and I wear XS with some extra length on me that I just bunch up a bit around my ankles. A reader, Jenelle, clued me in that Hue has a SKIMMER ankle length version, perfect for us short gals, so they don’t bunch at the bottom if you’re wearing flats.  She said they run a little bigger though.

Striped sweater leggings grey boots.1

Sweater 60% Off •  Ring • Necklace • Leggings • Boots 55% Off • Bag

Cardigan • Leggings • Similar Tunic Tee • Similar Scarf • Y Necklace • Earrings • Kids Women’s Hunter Boots 50% Off

Houston winters typically don’t require snow boots, but we DEFINITELY get use out of our rain boots!  I’ve compared the different styles of boots in the past and talked about being able to purchase kids’ sizes for adults!

If you don’t have a good pair of rainboots yet, I highly suggest investing in a pair.  I promise you’ll be so surprised at how many opportunities to you get to wear them and when you need a pair of rainboots, nothing else will do!  There’s nothing worse than walking around with wet shoes and soggy feet! *I bought the kids version because they fit me well- not too high, and they saved me money! Just subtract 2 to find your kids size! 

Pink Wrap Tunic • Leggings  TTS • Boots •  Similar Bag • Y Necklace

Leggings with black tunic and tall boots #fallfashion #winterfashion 4

Black Tunic S • Leggings XS • Boots TTS • New Version Faux Fur Vest • Bag • Rayne Necklace • Aviators • Bracelet • Ring Trio

Sweater • Similar Jacket • Tassel NecklaceLeggings XS • Boots • Savannah Zippered Tote

Red white stripe tunic and leggings

Tunic Sweater Now $30 Similar Vest •LeggingsBoots 55% Off • Savannah Zippered Tote  • Necklace

This tunic sweater was a most loved piece from 2017. I’m bringing it into 2018 with a vest and some knee-high boots. It’s long, warm and striped – currently all my favorite things!!


Sweater dresses and long sleeve dresses are still great options for cold winter days. They’re easy to style under a longer coat or sweater and add boots or booties with tights to keep your legs warm!

T-SHIRT DRESS : This Must-Have dress is a lightweight crepe material (think less wrinkles!) with sleeves, a chest pocket detail and a great v-neck cut (very flattering).  It comes in several pretty fall colors, and for less than $50, you’ll want to pick up a few! [[Major sale alert! The purple and sand are just $27!! The red, olive and rust are $33!!]] I have the black and navy and want the plum!  The mustard yellow would look so good with all the warm-hued fall scarves and on my brunette friends.  The dress fits TTS and isn’t too short, even on my girlfriend that’s 5’8.  It’s slightly longer in the back, with a higher cut on the side.  Also worth mentioning, is that this black dress is totally opaque, so you don’t need to worry about flashing!  You’ll need a cardigan or jacket with tights in cold weather though!

MAGIC DRESS : It’s not everyday that you find a dress that literally flatters every figure! This “magic” dress has the perfect amount of side ruching and a cute criss-cross “V” in front that lengthens your leg line! It comes in a ton of colors and also sleeveless for under $60!

9Fall Fashion Work Outfit #fallfashion #outfitinspiration

Black Skirt XS • Similar Sweater •  Earrings $6 • Similar Scarf • Tights • Boots • Similar Bag • Coat XS

2Fall Fashion Work Outfit #fallfashion #outfitinspiration

Black Skirt XS • Similar Sweater •  Earrings $6 • Similar Scarf • Tights • Boots • Similar Bag • Aviators

sweater dress.2

Sweater Dress 60% Off • Jacket • Boots • Necklace

pink sweater dress with grey scarf

Sweater Dress XXS • Boots • Similar Scarf • Similar Clutch  • Necklace

Fall Outfit - white bell sleeve sweater dress with dark red vest and knee high boots #fallfashion

Similar Dress • Similar Bag • Boots TTS • Necklace • Vest • Similar Scarf

I LOVE this white sweater dress – so did a lot of people as it sold out pretty quickly. I’ve linked a similar grey one by Eliza J that looks the same and with more fun sleeves!

Black shirt dress under $50.12

Shirt Dress XS Up to 40% Off ⋅ Suede Moto Jacket XS   Pendant Necklace ⋅ Hoop Earrings ⋅ Similar Black Bangle ⋅ Old Booties (new version 20% Off) ⋅  Watch ⋅ Ring Trio ⋅ Similar Clutch ·  Aviators

Project OneWay SugarLand Towne Square (3)
Magic Dress • Scarf • Booties 50% Off

Magic Dress

Magic Dress XS • Similar Poncho 50% Off • Boots • Tassel Necklace

Party Outfit- black tee with pink tulle skirt

Top XSP • Skirt XXSP 40% off • Similar Jacket • Similar Heels • Similar Clutch  • Similar Bracelet • Ring • Earrings • Aviators • Watch

This tulle skirt is so fun and flirty! I enjoyed spinning around and all the layers, though thin, actually made this a very warm look! The pretty rose color I have on in this picture is sold out but I found similar versions in Black, Peach and Pink.


And if you happen to be sitting at home in your pajamas today (like we are!) you might want to take advantage of these after Christmas sales from the comfort of your couch!

NORDSTROM • Great sales even though the Half Yearly Sale is over! This Maxi Dress is 25% off and this 40% Off Hazy Day tee looks great for LAZY days – or working out 🙂

LOFT • Free shipping on orders over $125. Check out this adorable Flounce Blouse and this COZY-looking Velour Open Cardi – both are an EXTRA 60% Off!!

ANTHROPOLOGIE • Extra 40% off sale items! This Lace Top looks like a great addition to your closet!

EXPRESS • Extra 40% off sale items! If I needed a work shirt, this one is under $30!

GAP • Up to 40% off! Refresh your tees for under $10!!

JCREW • Up to 75% off original prices! This is peplum and velvet… yes please!

OLD NAVY • Up to 70% off! Cute cami for under $10!


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Meet Megan

Hi! I’m Megan, mom to a thoughtful teenager and spunky young girl. We call Houston home and recently moved into our dream home. I traded my lawyer hat to become a full-time blogger in 2010. I love sharing my passion for affordable fashion, home decor, organization, & fitness to help inspire you to take care of you!


  1. What sort of coat do you suggest wearing over the long cardis? I love a long cardi but in Boston, a winter coat is a MUST when heading out doors (especially tomorrow with a -20 windchill). I always feel silly when my longer sweater is hanging down beyond my coat, but it seems only a full length jacket would solve that problem. Any suggestions on how to make it work?

  2. What is the list app you use? I remember reading about it; however, I cannot find it now. Are you still using it? I remember you said that you could add pictures to your lists.

    1. Hi! It was probably Evernote! It takes a minute to get the hang of it, but once you start using it, it can be really useful. I do still use it!

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