Heads up: Buying via our links results in us getting a commission (not always, but just about), which helps keep the lights on around here. We also take your privacy rights seriously. Head to learn more.
Welcome to the unhappiest time of the year. The winter doldrums are often cold, dark, dreary, sloppy, messy, and bleak. Which means it’s a perfect time to dress well, . Everyone is miserable! Which means a little bit of intentional (but not obnoxious) color can brighten a room, and possibly someone’s mood. Maybe that mood is yours. Maybe it’s your partners. Maybe it’s some public-facing worker who has had 27 schlubs be rude to him or her that day. A little effort and mutual respect can go a long way.
Dressed Up
The Suit: . From their less expensive . Italian wool, nice details and construction, ships and returns for free. Be aware that Suitsupply insists on making their jackets with functional sleeve cuff buttons, which admittedly is cool, but those can be expensive to tailor if they don’t fit the length of your arms just right. The less expensive option:
The Shirt: . Good quality and they do their best to keep them in stock.
The Tie: . Has some rich-looking texture, while costing less than a quarter of a hundred dollars. We’re working our way towards Tie Bar’s $99 free shipping threshold, so stand by for more picks from them…
The Pocket Square: . A muted brownish red, with a floral pattern signaling the season on the (distant) horizon. (checks math… okay we’re at $93 so far at Tie Bar, so…)
The Socks: . Cheap! Cotton and not wool, so you won’t get the wicking and temperature regulating properties that wool brings, but… again: Cheap! And now we’ve finally triggered the free shipping threshold at Tie Bar. So we got that going for us.
The Watch: : Sharp. Assembled in France. Powered by a Miyota automatic movement. Priced in euros. Free shipping and returns from France to the United States.
The Shoes: ($178). Recently restocked and (for now) are $30 off. They’re sleek, they’re made well, and the materials used are quite nice for the price. That and the subtle, rubber sole will help keep you upright on late-winters slick sidewalks and stairs. .
The Belt: ($110). Or whatever medium or even dark brown dress belt you have on hand. Style “experts” will say to try and match your leather accessories as close as possible when assembling an outfit… but most of us just really don’t care as long as they’re in the ballpark.
Smart Casual
The Blazer: ($300). Made from a soft, knit stretch-cotton flannel from Italy’s Emmetex mill. No shoulder pads. Soft construction. Will look just as good over a t-shirt as it would over an OCBD.
The Sweater-Polo: ($78). Spier knows merino. And this sweater polo is knit from 100% pure merino. The “denim” blue is, oddly enough, a perfect contrasting compliment to dark wash jeans.
The Jeans: . A much more affordable alternative to . Full .
The Watch: . . Really nice. Band it comes with is black, but with 20mm lugs that’s an easy swap out if you’d prefer a brown band to match your belt. But really, again, .
The Socks: . The best, most versatile socks on the market.
The Boots: ($475). Dark green suede that somehow remains subtle. Make sure you treat them with some before you head out into the muck that is the winter doldrums. Goodyear welted in Port Washington Wisconsin. On sale, but these should be first quality. So no restocking fee, no “slight cosmetic blemishes,” and they’ll ship/return for free.
The Belt: . The new standard. .
Athleisure
The Jacket: FINAL ($198). From their excellent, easy to move in, won’t make you look “puffy” Down for It All line. Note that this one is the jacket style that doesn’t come with a hood. Which some will prefer. Final sale though. No returns or exchanges. The (much) more affordable alternative:
The T-Shirt: w/ EXTRA50 and ships free w/ FS24 ($30). Part of the big Under Armour January clearance event. True performance wear here. Not cotton based. So it should wick and breathe and all that good stuff.
The Joggers: . 80% poly / 20% spandex. So built with more stretch than most.
The Hat: ($30). An inexpensive favorite. Acrylic/wool blend. Red, but not fire-engine red thanks to that heather-effect.
The Bag: ($110). They keep making these things because people keep buying and liking these things. Separate shoe compartment is a nice plus.
The Socks: . Excellent workout socks. Excellent casual socks. And they have flying outhouses on them, so, that’s a clear plus.
The Sneakers: ($135). Mostly gray but with pops of “bronzine.” Beefed up a bit for winter weather. They’re not mountaineering boots, but they’re better than, say, Chucks. Keep your expectations reasonable, and you won’t freeze your toes off by picking these over something truly waterproof if the weather is a disaster. Dark gray base should hide reasonable splashes of mud, dirty snow, etc.
The Watch: . . Really nice. One of Orient’s best. Deep green dial.