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Winter 2019 Lookbook

Creating and sharing lookbooks have been a long-time goal of mine. When you start to see clothing for how they move and fit and pair, it’s easier to get more creative with the pieces you already have in your closet (or find holes that need to be filled with intentional purchases).

The Winter 2019 Lookbook is a combination of some classic wardrobe items along with a few special pieces I purchased over the holiday season. I went into the beginning of January knowing my sweater collection was pretty woeful. I had a few college sweaters, some heavy winter ones, and 2 everyday sweaters – but South Carolina tends to be weather weird in the winter. I never know if we’re getting 50 degree days or 20 degree ones (2 weeks ago we were in the 70s!) so I had my eye out for medium to lightweight sweaters to add in.

Along the way, I found a couple sweaters, a pair of dressy black leggings, and a new pair of jeans to add to my closet. Then I was able to get rid of an ill-fitting pair of denim and tuck away the heavy sweaters in the off chance I may need them later in the season.

Below, I dive into what I bought, why I bought it, and how I can create multiple outfits out of the same pieces of clothing.

Accessories and Shoes

Throughout the winter (and fall and spring) I basically wear the same four pairs of shoes over and over. I love them, they go with anything I can dream up, and they’re already broken in. They consist of a pair of Chelsea boots, sneakers, flats, and heeled boots.

Chelsea Boots

From the Toms collection and my first foray into their non-classic shoes. I bought these before our Seattle/Portland trip and haven’t worn many other shoes since.

They’re comfortable, classic and a style I will keep on buying. The suede comes non-waterproofed, but I purchased a waterproofing spray on Amazon and they haven’t suffered much wear.

See the Toms Ella Boots

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Sezane Jack Sneakers

I bought these shoes a year ago from the Sezane store in Soho and they have truly been one of the best purchases I’ve ever made.

They’re comfortable, classic and look a little Golden Goose after wear. At first I babied them – only wearing on the best weather days – but then I realized they were only shoes and I wear them everywhere.

Shop the Jack Sneakers

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Brown Flats

Out of all of my shoes, I get the most compliments on these! They’re comfortable (can you sense a pattern?) and are unique.

I bought this pair from the Moorea Seal website in the color Camel, but I remember seeing the design first on the Free People website.

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Sezane Heeled Boots

These are by far the most trend-setting pair of shoes I own. Navy suede with a silk ribbon tie, I get nervous about wearing them out because I just don’t want to ruin them!

But for special occasions in the winter – these are my go-to! Pair with black or white they’re tres chic and make any outfit so elegant. This exact style is sold out on the site, but their 2019 winter collection of heeled boots are just as dreamy.

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Sweaters and Tops

Right as the weather was turning chilly, I did a once over of all of my winter appropriate sweaters and tops and realized I was still holding on to some college sweaters and ill-fitting/worn tops. It didn’t take long for me to send them out the door and I started browsing favorite sites and their sales to find quality tops to fill the gaps.

White Cowl-Neck Turtleneck

There’s something comfortable about a well-fitting turtleneck. It’s a classic piece that never goes out of style so I was excited to add this beautiful cream one to my collection.

I found it on the Banana Republic Factory site and have been wearing it nonstop recently with pants and skirts. It’s warm but not too chunky so I can easily pair it under coats and jackets for extra warmth.

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Madewell Chambray Shirt

This shirt was a bit of an impulse buy. I technically didn’t need another chambray shirt in my wardrobe, but it was deeply discounted during Madewell’s recent sale and it’s one of those perfect all-season tops.

I couldn’t find it on the Madewell store, but Nordstrom Rack was carrying it as well and the price is still great. I sized down because although it’s supposed to be loose, I didn’t want to look like I was floating in the shirt.

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Fancy White Top

If you’ve been around the blog for a bit, you know that I wear this top a shameless amount. In my defense, I can’t resist beautiful white lace. It has an elevating effect on every outfit I pair it with – from denim to dresses – and looks so chic in the winter under coats.

I bought this at Anthro last year, so it’s unfortunately not still around, but I rounded up a few others that I would snatch up immediately.

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Here’s the thing about coats – if you buy a couple really nice coats and keep them in good condition you may never have to buy another one in your lifetime! I truly believe in investing in timeless, quality outerwear and I’m about 2 coats away from hitting my “set for life” goal. You’ll see 2 coats in the lookbook video, but I just want to talk about the main one here.

Tan Overcoat

I think I paired this coat with almost every outfit in the lookbook #sorrynotsorry because it’s just that good! I bought it right before our NYC trip last year and it still looks brand new.

It’s a size 2 from J.Crew and although their coats tend to run large, I needed this one to be a tad big in order for it to fit over multiple layers. This is my go-to cold weather coat because I can actually wear 4 layers underneath and still button it up. If you wanted a more fitted version, I would size down at least 2 sizes.

This exact coat isn’t on the J.Crew site anymore, but everyone else raves about their Cocoon coat and that would have been the one I invested in had this one not worked out.

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Just like my tops and sweaters, I was also very aware of gaps in my pants collection. I have my go-to pants of course, but I was needing a few pairs of pants that I didn’t have to roll up at the bottom. I’m only 5 feet tall, so unless I’m shopping petite sizes I have to roll up all my pants. Time for some new ones!

I was actually really happy with what I ended up with and am just waiting on a new size of my dream black denim to arrive for this section of my wardrobe to be complete.

Lightwash Denim

Lightwash denim and I are having a moment right now and I’m not ashamed. There’s something delightfully vintage about lightwash jeans and I’m prepared to embrace that trend!

I bought this pair of Paige jeans from Poshmark – brand new for only $25! and they fit like a glove. But if you’re not into secondhand shopping, these pairs were also on my radar.

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You might be surprised, but I only included one dress in this winter lookbook. I love dresses, but in the winter I don’t naturally gravitate towards them. Bring them on the spring/summer/fall, but I truly prefer pants in the chilly months. That being said, the dress I do feature is a closet staple and I couldn’t image a lookbook without it.

Free People Midi Dress

Another one of those “good for every occasion” pieces, this dress from Free People is a must have in any closet. It’s chic, comfortable, and pairs well with boots and sandals alike.

When I first tried it on – 2 years ago now! – I was worried it might be a little too Little House on the Prairie, but after living in the magic of the dress I know it’s a must have.

It now comes in four different colors and I’m thinking about purchasing the Lagoon color for the spring.

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