Surviving Winter in Style

Key Purchases With An Eye Towards Fall 2025

Hi Friends. Hope you’re adapting well to normal life again following a hectic holiday season. After the holidays here in the North East, a hunker down mentality takes hold as we brace ourselves for the cold, dark and potentially snowy months ahead.

Central Park in the snow

Personally, I have a new appreciation for winter after sitting two of them out while I lived in Savannah. There is a stark tranquility to the season. Post holiday, life seems to slow down just a little. Dry January encourages more nights in, more time to read, visit museums or hit the theater. I find New York City the coziest place on earth in winter with wood paneled restaurants, the beauty and silence that blankets the city after a snowstorm and the refuge of our own snug apartments.

The wood paneling alone is worth a trip to the Cooper Hewitt museum, formally the private residence of the Carnegies

I may be romanticizing a bit here in the beginning for January. My feelings in March may be a different story, but for now I’m fully embracing it. I’m also embracing full-out winter clothes because damn, it’s cold out! Post holiday is a great time to add a heavy duty sweater or boots to your winter mix with much of it on sale.

Classic cozy, the Frank Lloyd Wright house at the Metropolitan Museum of Art

I’ve made an exhaustive search resulting in a selection of worthy buys that have staying power. The full edit is in my recently opened ShopMy store you can visit here. The store will serve as a place to view my edits for What Looks Good. My promise to you is I will only feature items that I consider a good value, made of high quality, mainly natural fiber fabrics, designed with integrity and for longevity. All are wardrobe builders that fit my mandate to buy less but buy better. Everything featured I personally love and would buy myself, and trust me I’m picky.

The Pre-Fall 2025 collections that began to show in mid-December give us a glimpse of what’s to come and informed my choices. Let me reiterate; sale purchases should be just as scrutinized as full price. I shop sales to find high quality pieces I need, blessedly avoiding the sticker shock that comes with luxury clothes now. Though I don’t limit my picks to only sales. The most important thing is to buy the right pieces that compliment your wardrobe and expand possibilities. Another criteria I set for myself when shopping is: will I want this in my closet for the next ten years or longer.

This edit focuses on sweaters, coats and boots with a subcategory I’ll call soft clothes (a term coined by my bestie Eric’s mom). These are the comfort clothes you change into when you come home. They also pose an opportunity to elevate your lounge looks. Comfort is key but you can still slay.

First up, these fabulous ankle boots from Cos (on sale but going fast!). They are similar to the Phoebe Philo boots I coveted until I tried them on, as you may recall, in “A Trip To Bergdorf Goodman”. The exaggerated width of the toe box on the P.P. boots made them feel clownish; see the white boot in the photo above. The Cos boot has the general shape but the width is trimmed down to perfection. Bonus, the heel at 2” looks refined while still comfortable; a difficult category to fill.

The above outfit is the perfect antidote to the winter doldrums. Each piece offers flexibility to a wardrobe that is grounded in black. The sweater and pants work well with your black staples and together give you a new color palette, while still working with your black accessories. I saw these suede pants in the Sézane store and could not believe the price. The real suede looks and feels great and I love the color. I also love the cut of the pants, which is flattering and perfect for oversized winter sweaters. Here, I’ve paired them with the COS boots, but for a more casual look you could go with a flat boot, sneaker or loafer. The pants can be treated as an elevated jean, which makes them a great addition to any wardrobe.

The striped sweater in a wool and cashmere blend adds a sporty touch and relief from all the dark solid sweaters of winter. The cut is just the right amount of oversized and the heavier weight gives it a luxurious feel. To tie the tan with dark brown stripes back to the black boots I added a black cashmere triangle scarf (50% off!) to the neck. A triangle scarf is a beautiful thing. I made them when I worked at Calvin Klein and still have 3 of them. I’m not kidding when I say I couldn’t survive the winter without them. They’re versatile, warm and you can tie them many different ways. I lost one in the Madrid airport, it was my travel buddy for many years, and I still mourn the loss of it. The triangles are often the piece that literally ties the outfit together. I’m happy to see that a few companies are now making them. Aritzia has a less expensive version, on sale here. Trust me, they’re a great thing to own. Last, these COS earrings are just too good-looking to pass up. I love how the backs are integrated into the design and going forward it’s all about chunky jewelry. They’re the perfect size and 40% off!

This coat is on sale and is another COS offering that is too good not to mention. I love the details and longer length. It’s roomy enough to wear over layers and thick sweaters. On those super cold days when you just can’t bear to put on that puffer again, this is a great alternative.

What’s more luxurious than coming in from the cold and swaddling yourself in cashmere? Light that fire, stream that moving and relish the comforts of winter! You deserve it! I’m not a big advocate of sweatpants unless they’re in cashmere. The above from White and Warren are quality and the cut is just right. Most brands make them too baggy for my taste. Quince also has them for less, on sale now in multiple colors here. I love the style of this COS sweater (what can I say, COS is hitting this season). Great for lounging but too good to only stay home in. COS also makes cashmere socks an affordable luxury, I love them in pink, also available in a two pack of neutrals on sale.

I hope this inspires you to hunker down for winter in style. There is much more of the edit here. I do receive a small commission if you buy from my links and store, which makes my work at What Looks Good possible. I’m grateful for your support! Thanks for reading and I would love to hear your thoughts on winter style and how you manage the cold, dark days of winter.

xxx Jolain