Style Scenario: Dressed Up while Avoiding the Winter Doldrums

What are you going to wear? Sometimes it’s good to look at a few suggestions then add your own tweaks and ideas. That’s what these are for. It’s cold. It’s dank. The sun hasn’t shown itself in some parts of the Northern Hemisphere for what feels like forever. What better time to inject a little bit of subtle color into your look? We’ll cover three levels of dress over the next couple of days (smart casual, dressed up, and dressed down). Cheer up buttercup. We’ll get through this together.

The Sportcoat: Bonobos Jetsetter Italian Wool Sportcoat – $208.80 FINAL w/ FROSTEDTIPS ($400). Lightly constructed, an unlined back, made from Italian wool, and has easy to tailor, non functioning sleeve button cuffs. Northern Lights people. Embrace wearing darker pants and a lighter sportcoat.

The Pants: J. Crew Wool Bowery in Slim or Straight – $35.99 FINAL w/ GETSHOPPING ($128). A nice, dark, but leaning more true-blue than navy wool pant that adds just enough color without getting nuts.

The Shirt: Made in the USA Brooks Brothers Button Down – $79.50 ($95). A little spendy, but a timeless classic that’ll wear well and last for a very, very long time. Available in all four of their fits, including regent (slimmer but not a true slim) and milano (a true slim).

The Topcoat: J. Crew Factory Wool Blend Topcoat in Navy – $101.99 FINAL w/ GOODDEAL. Noticeably darker than the bowery pant. A little blue on blue never hurt anyone during the darkest, bleakest time of year.

The Gloves: Club Monaco Racking Cuff Glove – $62.65 ($119.50). It’s gloves-on-sale season. These get an extra 30% off at checkout, no code needed.

The Briefcase: Fossil Waxed Canvas Work Bag – $137.99 ($198). Doesn’t appear to have any noticeable branding? Which can be rare for Fossil. Waxed canvas and leather accents = a nice high/low look here.

The Scarf: Polo Ralph Lauren Stripe Wool & Cashmere Scarf – $46.80 ($78). Just 5% cashmere, so don’t think it’s a 50/50 blend or anything. Nice stripes. Ships and returns free via Nordstrom.

The Boots: Banana Republic Louis Chelsea – $72.59 ($178). A very nice price for an entry level Chelsea boot. Full review here. Extra 40% off happens at checkout. No code needed.

The Belt: Banana Republic Italian Leather Belt in Cognac – $41.50 ($59.50). Or, whatever lighter brown belt you might have on hand.

The Sunglasses: Made in the USA Shwood “Cannon” 54mm Polarized Sunglasses – $101.40 ($169). A bit of an investment, but they’re made here in the states, have a really nice updated wayfarer look going for them, and the lenses are polarized.

The Watch: Orient Bambino 2nd Generation Version II – $169.00. The perfect balance of retro inspiration and modern automatic watch affordability. Hacks and hand winds. Review here.

Coming up tomorrow, we’ll brighten things up during the doldrums with a real casual outfit.

Joe

Recent Posts

Huckberry: 15% off Sitewide Annual Sale

72-hour merino shirts. 365 pants. Blazers and chore coats. Hamilton watches, Italian made boots, and…

17 hours ago

The Best Men’s Style Sales for Singles’ Day / Veterans Day

Spier topcoats, Grant Stone tiers, and Bonobos does a surprise inclusion of their icon Weekday…

3 days ago

Skimp, Spend, Splurge: 10 Types of Fall & Winter Coats & Jackets

Exploring 10 styles of men's outerwear, each with specific options at three different price tiers.

3 days ago

Bonobos 30% off most Pre-Holidays Sale

Now extended through Thursday. It's their "Treat Yourself" event. Select flagship chinos. Stretch premium jeans.…

3 days ago

Steal Alert: 40% off most everything at Brooks Brothers

48 hours only. No bulk buy or rewards club requirements. Just a flat, 40% off.…

3 days ago

Most Wanted Affordable Style – November 2026

Roaring 20s styled watches, restocked half-canvas suits under $300, & more.

4 days ago