Winter Outfits
Winter outfits are always a struggle for me. I find that I have a difficult time pairing different things together. It’s probably because my closet is full of Lilly Pulitzer. These temperatures below 30 do not exactly scream Lilly Pulitzer wearing weather.
I will say I’m very grateful to have power back after this storm that went through on Monday. We got power back late on Thursday and then the internet and phone came back later. However, our phone and internet keep going in and out.
I will say one thing I’m having a hard time finding this year is a nice winter dress. Everything seems to be midi length and I am not here for the midi length. Likewise, it seems that the Little House on the Praire look is continuing.

Cotton Teddie Sweater | $35 (sale) | This is a tried and true item that I keep going back to year after year.
Jeans | $50 | These jeans are just a suggestion; obviously as far as winter outfits go, you can wear any jeans that you’re comfortable in! My J.Crew Jeans have lasted me since college so I know they will continue to last for a long time.
Long Sleeve Henley | $27 | I love how easy this is to mix and match!
Cozy Belted Wrapped Sweater | $35 | I would wear this with a basic tee or tank underneath it. I love wrapped sweaters because they give the impression that you’re dressed up more than you are.
Off-White Jeans | $40 | I’m here for a good winter white pair of jeans. This will definitely fit the bill! Wear them with a darker colored sweater or shirt.
Dolman Sweater | $70 | This is a Loft sweater-and one perk of Loft is they often have a sale.
Long Sleeve Mini Sweatshirt Dress | $40 | I love these dresses. I have multiple. Pair them with boots and you’re good to go!
Curved Perfect Skinny Pants | $90 | Again, these are from Loft, so they’re on the more expensive end. However, I will say I love their pants. They also have these in regular (not curvy) fit.
Skinny Corduroy Pant | $70 | I got multiple pairs of these my first year teaching (in my district we’re not allowed to wear jeans unless it’s Friday or we have a jeans pass). I love them. They’re great for moving around all day, sitting on the floor, getting dirty, etc. I love the color options they have for these.

Wooly Button Pocket Skirt | $70 | Again, a pricier item; however, this is a skirt that will last you for years. This is a skirt that can go with any color top. Add a cute pair of riding boots and you’re out the door! Skirts might not seem like they should be part of winter outfits; however, I love a good winter skirt.
Ikat Jacquard Skirt | $70 (sale price $60) | Match this skirt with a white top and you’re good to go!
Adler Skirt | $98 | As this is a Lilly item it’s definitely on the more expensive end. However, I will say this is an adorable skirt that will make a great statement! This is paired on the website with an Elsa top; however, you can pair it with any solid top (especially black).
Spanx Faux Leather Leggings | $98 | Y’all, these are the best investment you will ever make in a pair of leggings. I wear them all the time, they’re comfortable, and they really make a dressy look. You cannot go wrong! I love shopping for Spanx products at Nordstrom-especially now that Nordstrom is now part of Rakuten again! If you haven’t joined Rakuten, sign up here. Every quarter you will get money back either via check or PayPal.
Sweater Dress | $58 | I love this! So cute and comfortable, yet dressy at the same time. It is a chenille fabric, so it is super soft (warning-before you wash it, the dress will shed). I would pair this with a navy or black scarf and a pair of riding boots.
Frye Melissa Knee High Boot | $368 | I know, I know. Almost $400 for a pair of boots? Yes. I’m telling you this will be a purchase you will not regret! My Frye boots have lasted me since my freshman year in college (10 years!). I love them and I’m obsessed with them. Sam Edelman also makes a comfortable boot and is a fraction of the cost ($156 on sale!)
Ariat Dixon Bootie | $189 | Y’all-these are expensive, but if you buy them they will last you for YEARS. Ariat is a known western brand boot that also branched out into the English riding world. You cannot go wrong with a pair of these. I used to not be able to wear them; however, they redesigned their footbed recently (I’ll be honest I’m not exactly sure when), but it was a GREAT move for them. They also come in a calf hair bootie, which might be the ones I end up with.
PJ/Lounge Top | $15 | Match this PJ/ lounge top with any of the more casual items (I wear “lounge” tops out all the time for a more relaxed look).
Jogger | $20 | Pair this with the lounge top for ultimate relaxation at home. If long pants aren’t your thing, that’s ok! Pair it with these shorts ($15!).
Here are some more winter outfits essentials. Remember, don’t buy anything unless you’re truly going to wear it!
Which piece is your favorite?
xx,
Lindsey