Old man winter is knocking on the door so I’m here to hit you with affordable and stylish options for your winter wardrobe. As you tuck away your summer wardrobe, the following winter must-haves are the perfect complement to the basic building blocks for a frugal, functional, and fashionable wardrobe outlined in the classic Mr. Everyday Dollar post The Clothes Every Guy Should Own.
The total for all ten of these items will run about $550 (less than the cost of five Kanye West white t-shirts!). While that’s a decent chunk of everyday dollars, keep in mind that all these items are classic and timeless pieces, meaning they won’t go out of style overnight. Think of them as an investment to keep your winter wardrobe functional and fashionable for years.
1) Snow boots
A pair of heavy winter boots need to be waterproof, insulated, and breathable. The Sorel 1964 Premium T boots in Tobacco meet these requirements, plus have that timeless beard-and-flannel-shirt look. Retail is $140 on Sorel’s site, but can be had for less than $100 on Amazon.
2) Wingtip boots
You can’t go wrong with a pair of $80 Beeswax Clarks Desert Boots as everyday footwear (fact: I wore mine out and had them resoled). The sturdy and versatile Sebago Hamilton, however, is a winter-ready waterproof leather boot that looks great with chinos, jeans, and corduroys. They run big so you’ll want to size down a half size. From Sebago $199, but they go on sale at Amazon for $100.
3) Wool socks
A couple pair of hearty wool socks will keep your feet warm throughout the winter. Wigwam knits these Merino Wool Socks (65% merino wool/27% stretch nylon/8% spandex) in Sheboygan, Wisconsin. Both The North Face and Smartwool socks don’t live up to the quality that these Wigwams do. Available on Amazon for $12/pair.
The J. Crew Bayswater is the peacoat by which all other pea coats are judged. The overall cut, the arms, the shoulders – it’s absolute perfection. The drawback is that it’s expensive, but around the February/March timeframe they will go on blowout sale. The Thinsulate version in Black, regularly $275, can be snagged for just over $100 when J. Crew clears their inventory.
A pair of high-tech ski gloves will look out of place in many situations (read: most). What you want is a pair of leather triple-top-stitch gloves, like the cashmere-lined light brown pair from All Gloves. Bluefly sells them for $69, and about $50 on sale.
A bright scarf will add a boost of color to a dark peacoat (see: #4). Don’t know how to wear one? The playboy look of the 4-in-hand knot (how-to video here) is a good bet. For $15, the Sierra Trading Post Lambswool is a great option.
7) Chunky cardigan or pullover
Instead of rocking a jacket or fleece, invest in a heavy knit cardigan or pullover to wear throughout the fall and winter. Look for a great cable pattern and no zippers – less suburban dad-ish – like this $80 (after 40% off coupon) shawl-collar pullover from Banana Republic.
8) Heavy belt
You need at least one belt. Make sure it matches the color of your footwear of choice. GAP makes reliable and cheap belts in both brown and black that last for years. Regularly $30, a 40% coupon brings it under $20.
9) Colored corduroys
After you’ve covered the workhorse colors of grey and brown you can get a fun pair of cords. Slim to your body is the name of the game here, so choose the Levi’s 514 cut if you have tree trunk size legs, or opt for the slimmer lines of the 511 if you’re leaner. Retails for $58, at Amazon for $35, but regularly on sale at the $25 price point.
10) Chambray shirt
If you’ve invested in the shirts that create the foundation of a wardrobe, your next step is Chambray. Inspired by blue collar wear, it looks just as amazing if you’re a laptop-toting cubicle jockey. $20 from Old Navy, but it may need to be tailored to bring in the sides and sleeves to skim the body, which should cost around $15.