Chinos, Chukkas, Polo: Brown, Olive, and Blue (and a jacket for fall)

About the Author: Adam Terry is a thirtysomething salesman in the construction industry. He enjoys whiskey, watches, boots/shoes, family time, and working on his dad bod father figure.

Chinos, Chukkas, and a Polo is our ongoing series out to prove the benefits of this simple combination. There’s a million ways to do it, the benefits are numerous and significant, and it can be executed at all levels of style budgets. Head here for a further explanation as to why chinos, chukkas, and a polo works. Click here for the growing archive. 

The Polo: Rhone Delta Pique Polo in Navy – $88. Rhone’s Delta Pique polos are simply the best performance polos on the market and I’ll fight anyone who says otherwise. They have a trim, but forgiving cut that’s great for everyone – including those of us who are still carrying around a few extra Doritos Locos tacos. The fabric is lightweight, very breathable, and holds its shape wash after wash. Best of all, they have hidden buttons underneath the collar to help keep it looking great all day. The more affordable option: Target All in Motion Performance Jersey Polo – $20

The Jacket: J. Crew Denim Trucker – $103.60 w/ SHOPNOW ($148). Denim jackets are about as American as apple pie, modern era baseball, and bourbon whiskey. They’re incredibly versatile and perfectly fill the lightweight jacket niche for these transitional weather “shoulder” days in between seasons. The most classic, all-around stylish version is the Levi’s Type 3 “trucker” jacket that was introduced in the late 1960s. My favorite modern, readily available version is this one from J.Crew and while the specific washes and colors will vary from year to year, you can almost always find one in a dark to medium wash that pairs well with everything but other denim. For sizing, you’ll want to size up a little as it’s a layering piece.

The Chinos: Bonobos Stretch Washed Chinos 2.0 in Caper – $99. A well-fitting pair of chinos will go a long way to elevating your style game above those around you. In 2023, the most popular and most versatile fit is a straight or slightly tapered cut that fits your frame well, allows for some flexibility and comfort, and lets the fabric drape. Avoid skinny or aggressively tapered cuts and make sure you get the pants hemmed. I highly recommend these Bonobos stretch washed chinos as they fit well and the stretch fabric feels very comfortable. The more affordable option: Check out J.Crew Factory’s Flex chinos for around $40 on sale.

The Sunglasses: Spier and Mackay Model 05 Sunglasses – $45 ($55). Over the years, I’ve tried numerous pairs of sunglasses from various brands at varying price points, but I always come back to Ray-Ban’s utterly fashionable Wayfarers… yet they can get pricey in a hurry. Spier and Mackay make an excellent homage, complete with polarized lenses, for noticeably less.

The Watch: Orient Ray Automatic – $165ish. Reviewed here in the most recent edition of the Double Time series. The Orient Ray is a versatile, do everything diver. The 41mm case diameter wears a touch smaller, so it looks as good with a suit and tie as it does with chinos and a polo. In-house automatic movement. Bezel has nice, snappy action. While the bracelet does have some polished inset bits between the center track and outer links, it’s subtle enough to still wear casually. It’s not overly gleamy.

The Belt: Nordstrom Rack Made in Italy Suede Belt – $40. Add a visual break and some texture to your otherwise simple outfit with a suede belt like this one from Nordstrom Rack. For casual outfits, it’s not imperative that your belt perfectly matches your shoes; just try to match the overall formality with a similar color tone and texture. You should still avoid the Menswear 101 faux pas of wearing a brown belt with black shoes, though.

The Socks: Darn Tough “The Standard” Crew Lightweight Socks (Navy) – $24.  If you haven’t heard, Darn Tough socks are the de facto Dappered mascots (they might not know this either, to be fair). They’re made well, super versatile in terms of style, feature merino wool that helps keep you cooler for longer, and offer an incredible value because you’ll use them every day. Plus, they are made in the USA and have a lifetime warranty. My go-to is “The Standard” crew lightweight option that can pull double duty as both casual socks and dress socks if you’re not a fan of the over-the-calf style. The more affordable option: Check your local TJ Maxx/Ross for “irregular” Darn Tough socks. These have small fit or shape issues and won’t have the lifetime warranty, but they’re usually under $10.

The Chukkas: Nordstrom Blaine Chukka Boots – $101.95 ($119.95). Recently reviewed, these budget-friendly chukka boots from Nordstrom straddle the line between business casual and relaxed casual pretty well. Dress them up with a button-down Oxford and chinos for days in the office, or dress them down with a polo and dark denim for a simple but effective smart casual outfit for running errands, date nights, and social events.

Want more of these Chinos/Chukkas/Polos outfits? Head here for the archive. We’ll be rebooting this series as the warm weather rolls on with currently available items. But this is the archive if you want it.