Five winter wardrobe staples that will never go out of style

After Thanksgiving, I finally pulled out my box of winter clothes from the back of our spare closet and began the process of organizing my closet for the cold Chicago months ahead. Although some people might find it tedious, I actually enjoy the process of changing over my closet each season. (Granted, it helps that I usually have a glass of Malbec in hand and Yo Yo Ma to keep me calm and centered.) 

It's a great time to reflect on my purchasing habits the past year, and analyze what's actually been working for me. There are a number of things that have stayed relevant every winter because they were high quality investment pieces in really simple, classic shapes that I can wear casually, dress up for a party, or toss on for work. Here are the top five purchases that have come out of my winter box every season, dating back to 2008:

#1 A long, slightly over-sized wool coat

In my opinion, a really great coat can make you feel stylish all winter long regardless of what you wear with it. The one I'm wearing in this picture is a Vera Wang wool-and-leather single-button blazer style that I got for a steal and wear constantly. It's roomy enough to wear over a suit or bulky sweater, and is so simple it works great tossed on over jeans and a tee shirt as well. It won't date because it doesn't have complicated tailoring or other adornments.

#2 Dark wash wide-leg jeans

Sure, skinny jeans had their moment for several years but wide leg jeans will never go out of style - they've been around forever and look good on almost everyone. I purchased the wide-leg Joe's Jeans that I'm wearing in the photo above more than seven years ago, and have worn them every season.

#3 A giant cashmere scarf 

I could write an entire post about how much I love this cream cashmere scarf (in fact, I'm wearing it with my pajamas as I write this): it's practical, comfortable, and adds an element of luxury to almost everything you pair it with. (Had I more self-esteem, I would insert a picture of myself in my giant gray sweatshirt, glasses, Retinol cream and this scarf to prove my point.) It cost a lot, but the cost per wear over the years has been pennies. My only regret was not picking it up in multiple colors.

#4 Slip-on leather ankle boots with a small heel and no hardware

My sister picked up the perfect pair of classic leather ankle boots from the Gap years ago, and I loved them so much I hunted them down on eBay and bought two pairs (in taupe and black, pictured below). They look like Isabel Marant but were super affordable, and are a no-fuss, snow-friendly and stylish solution for mornings when I really feel like wearing my UGGS to work but know that my professional reputation can't absorb that kind of atrocity. Simple, slip-on, and unadorned black boots are pretty hard to find but worth waiting for the right pair.

#5 Black cashmere-lined leather gloves

For some reason, cheap mittens and gloves irritate me - they're impractical, and they make everything else look cheap too. They are the winter style equivalent of a seriously chipped DIY Sally Hansen manicure. You really need just one pair of gloves, and they should be the best quality you can find and simple enough to go with all of your coats, hats, earmuffs and scarves. Black leather goes with almost everything, including every single one of my hats like wool berets, cashmere beanies, Russian fur hats, etc. My black leather gloves have been with me for ages, and I love that they give an expensive touch even to a cheapie American Apparel knit beanie as pictured above.

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