What are you going to wear? Sometimes it’s good to look at a few suggestions then add your own tweaks and ideas. The old saying goes something like “If March comes in like a lion, it’ll go out like a lamb.” Alternatively, it could come in like a lamb (a false spring) but then expect it to go out like a lion (cold and blustery heading into April). This one’s for those plugging along right now through lion-like cold, rain, and general unpleasantness. If your weather is more lamb-like, we’ll get to that soon.
For this “Lion” scenario, note two keys to dressing well when the weather is wet and generally unpredictable:
- Wear machine washable pants instead of dry-clean only suit pants or trousers (in case some of the slop splashes/splatters up on your legs).
- Favor versatile, weather resistant shoes or boots with a subtle rubber sole.

The Raincoat: Charles Tyrwhitt Showerproof Cotton Raincoat – $319.20 w/ PROPER3 ($399). Bit of a splurge, but the Brits know how to look good in the rain. That and if you can invest in a piece of versatile outerwear, it can be worthwhile. As you’ll wear it with everything and in almost all conditions. Doesn’t get more versatile than a simple, classy, navy mac. The More Affordable Option: Cole Haan Signature Raincoat – $169.99 ($300)
The Sportcoat: Rodd & Gunn Textured Wool & Cotton Sport Coat – $224 ($448). Interesting but still reserved. 61% wool, 37% cotton, 2% elastane. Non functioning sleeve cuff buttons. Ships and returns for free via Nordstrom. The More Affordable Option: Charles Tyrwhitt Sweater Blazer Cardigan – $129 ($209)
The Shirt: Target Goodfellow Performance Dress Shirt – $33. Inexpensive and pretty good. Reviewed here in white.
The Watch: Timex 40mm Marlin Moonphase Green Dial – $169. Fun, but still dressy. 40mm case diameter should work for most wrist sizes.
The Pants: BR Factory Slim Tapered Grayson Pants in Grey Glenplaid – $45 ($100). Clearly going for a British gentleman look here. Dressy but still machine washable. Know they run a little short, so if you’re inbetween inseam sizes or unsure, size up. My 5’10″/185 takes a 32″ inseam on these, whereas I can sometimes take a 30″ depending on the brand/pants. Here’s how a 32×32 in the light blue looks on my frame.
The Umbrella: Totes “Gentleman’s” Wood Handle Umbrella – $23. A classic that provides good coverage but isn’t as large (or as obnoxious) as a monster golf umbrella. The hooked handle allows you to sling it over your arm/wrist when you need that hand to open a door or grab your phone.
The Socks: Darn Tough The Standard Merino Blend Socks – $27. Just the right amount of cushioning without getting bulky or thick. Made in the USA.
The Boots: Allen Edmonds Weatherproof Hamilton Dress Boots – $199.97 ($495). Goodyear welted to a rubber studded sole. Weatherproof leather. Ideal for this scenario.
