$100.00 $54.01 (46% OFF)

Rain jackets are a tricky category. Some work but are too hot on the inside, while others are the opposite. Marmot, for the price, balances both pretty well. It’s breathable yet waterproof, and, because it’s far simpler than most other options, looks good while doing it.

$14.99 $9.98 (33% OFF)

Cushioning separates good socks from the great ones. No, dress socks don’t have any — and there are some excellent ones out there — but no one ever wears them for their comfortability. These Hanes, however, are plush to the max. 

$98.00 $49.00 (SELECT SIZES 50% OFF)

Unlined trucker jackets wear well deep into summer. Sherpa ones, however, would leave you sweating through. Cop this one while it’s on sale and shelve it until the season changes.

$36.00 $22.50 ($14.50 OFF)

One of our readers pointed out that Columbia’s PFG shorts are an excellent alternative to Patagonia’s ultra-popular Baggies. They were right! These boast many of the same qualities and come in a ton more colors. 

LIKE PATAGONIA BAGGIES? THEN YOU’LL LOVE THESE SHORTS, TOO

$98.95 $89.95 (10% OFF)

Sealed seams and a DWR finish render TNF’s Venture 2 jacket waterproof. But, it remains ultra-light, packable to 1/10th its size and a solid top layer no matter the forecast.

$160.00 $120.00 (25% OFF)

A bomber jacket is a pillar style as far men’s jackets goes, and Alpha Industries’ MA-1 option combines classic elements and modern touches quite well. It’s a complete choice for anyone new to the shape or well established in their ways.

$89.00 $53.35 (40% OFF)

The quintessential quarter zip done by the outdoors experts at The North Face. A super-sweet deal on one of the best damn jackets out there.

$38.00 $29.90 (21% OFF)

While pullovers are probably more popular, the zip hoodie offers breathability and a different look entirely. American Apparel’s ultra-soft, unisex fleece option comes in several colors, each with contrasting white ties. 

SHOP THE BEST SWEATSHIRTS FOR MEN

$89.50 $46.40 (48% OFF)

It’s difficult to name another piece of clothing more important — at least to my wardrobe — than a Levi’s Trucker Jacket. It set the standard for top layers and has been steadily produced ever since. Cop one in classic Indigo or several in an array of washes. There are plenty to choose from.

$47.95 $28.49 (41% OFF)

Wedding season, after a year-long hiatus, seems to be in full swing once more. Maybe your go-to shirts have gathered some dust. Refresh your inventory with this simple option by Calvin Klein. They’re cut to fit a ton of different neck and sleeve sizes and are on sale in a few different colors. You can never go wrong with white.

$95.00 $66.50 (30% OFF)

You aren’t beating Lacoste’s classic Pique Polo. It comes in array of colors — like 15, if we’re counting — and sizes. There’s this one, called Boabab Green, but get yours in your favorite hue; they’re heavily discounted. 

$248.95 $149.35 (40% OFF)

One of The North Face’s most advanced jackets, the Carto Triclimate features lightweight insulation to combat colder weather, a DWR finish for water resistance and zip-in construction on the inside for seamless integration with other TNF products.

$39.50 $31.65 (20% OFF)

There are several differences that separate board shorts from swim trunks. This Quiksilver pair falls under the former, because it boasts a longer inseam. 

$15.00 $14.10 (6% OFF)

Sure, this isn’t the biggest steal you’ll see on Prime Day. But every penny counts, right? Plus, these are underpriced to begin with. They’re solid T-shirts constructed from a blend of polyester and cotton and tailored to be well-fitting. (Tip: save an extra 20% at checkout.)

SHOP THE BEST BASIC T-SHIRTS FOR MEN

$42.50 $26.68 (37% OFF)

Treat yourself. It’s time to upgrade those dingy drawers you’ve been holding onto since high-school. (Honestly, really hope you haven’t been.) Either way, these 95-percent cotton, 5-percent spandex boxers offer stretch and comfortability and cooling properties. 

$69.50 $41.70 (40% OFF)

The 511 is Levi’s slim fit jean. It’s as cared for as the 501, if that makes sense, so there are dozens of washes and they’re available with the Water<Less marker — meaning they've been made using significantly less resources.

READ ABOUT ALL OF LEVI’S FITS

$98.00 $78.40 (20% OFF)

Well, well, well: Alex Mill’s high-quality clothing makes its way to Amazon. Score on this super-soft, mid-weight French Terry sweatshirt while it’s on sale.

$53.70 $49.99 (7% OFF)

This already reduced Calvin Klein denim jacket — in an almost suede-looking color called Bronx Light — exudes an aura of luxuriousness typically unfound at this price. Plus, it’s nearly-neutral tone pairs well with most other earth tones.

$24.99 $19.99 (20% OFF)

Dockers’ classic short works as well on the deck as it does dinner. It’s a no-frills take on the chino short, a summer staple everyone should own. Yeah, the 10-inch inseam is longer than most want theirs to be, but we’ve all seen “Sandlercore” making the rounds.

$57.00 $49.00 (12% OFF)

From Kanye West and Justin Bieber to A$AP Rocky and skaters worldwide, Dickies have been donned by many. Get in on the madness with this unlined Eisenhower jacket. It’s workwear done well that pairs with almost everything. 

$16.81 (SAVE 20% AT CHECKOUT)

Nothing beats busting out a brand new pair of white socks. Gildan’s are soft, feature arch support and don’t lose their shape after a few wears. 

SHOP THE BEST EVERYDAY SOCKS FOR MEN

$42.00 $24.99 (41% OFF)

Give white pants (and workwear) a whirl without emptying your wallet. Dickies’ Original 874 pants are well-loved for several reasons: they’re durable, well-designed, relaxed through the legs and available in an array of colors. Plus, the cut is somewhere perfectly in-between skater and industrial uniform.