Written by 10:28 am Economics

43 Sharp Men’s Style Picks As We Leave Summer and Head Into Fall

We’ve done the shopping for you to make style easy.

Traditionally the market teaches us that there are four seasons and our wardrobes magically switch from summer shorts to fall flannels from one day to the next. But in real life, of course, our wardrobes are always in a constant state of transition – both from one season to the next – but also in evolving our personal styles from where we are to where we’re going. That may be because of our style needs changing due to life or work circumstances, or our aesthetic preferences shifting as we age and trends progressing.

Whatever the reason, the most important part of a changing wardrobe is finding resources to serve as thought-starters and inspiration and are shoppable for one-and-done ease for the guy on the go. For that reason, we’ve “gone shopping for you” as the season – and our personal styles – transition.

image of a man wearing a green jacket over a white shirt

Garment Dyed Surplus Jacket

Madewell, $54.60

One of our favorite types of jackets, the field jacket is an easy way to (surprisingly) elevate both casual and smart casual outfits. See how to wear a field jacket in our full guide. This one from Madewell is lightweight, a perfect update to the one I picked up from J.Crew Mercantile several years ago, still wear, but is now out of stock.

image of a pair of white sneaker shoes

Advantage Eco Sneaker

Adidas, $48.50 $70

A visual child of the classics Adidas Stan Smith and Nike Killshot, this vegan offering from Adidas adds detail in the marled sole.

image of a short sleeve button up shirt

Sierra Dobb Chambray Shirt

Pendleton, $39.75 $79.50

A simple, refined pattern in a handsome muted red/pink, easily worn with shorts or under layers for a more put-together look.

image of charcoal grey twill pants

Slim Fit 5-Pocket Stretch Twill Pant

Amazon Essentials, $21.10 $24.90

A slim, 5 pocket twill pant in charcoal is easily the most versatile pair of pants you can own. Throw in some stretch and they’ll be your favorite too.

image of grey cotton shorts

5.5″ Cotton Casual Shorts

Amazon, $27.98

For the man who likes shorts to actually be short, these grayish-blue steretch waist shorts are an easy pick for the end of summer.

image of a person wearing a crewneck sweater and slim fit pants

Lambswool Crewneck Sweater

Goodthreads, $55.90

Fair Isle sweaters have a long, storied heritage, and pair well with most aesthetics, from preppy to streetwear and everything in between.

image of a green sport coat

Cotton Unstructured Sport Coat

Spier & Mackay, $248

The unstructured cotton sportcoat is probably the most useful blazer a modern man can own. It can be easily worn in place of a regular jacket with casual outfits made up of jeans and t-shirts, or can be worn in smart casual outfits for work or dates with a dress shirt, trousers, and boots.

image of a floral print button up shirt

Floral Print Short Sleeve Shirt

Spier & Mackay, $58

There’s no question that floral shirts are both modern and historical and are a sharp option for any guy: The trouble is finding a gentlemanly pattern that can be worn casually or more put-together. This one from Spier & Mackay (one of our 32 best clothing brands for men) nails it with the muted color palette and moderately-sized pattern.

image of a blue long sleeve chambray shirt

Denim Western Shirt

Spier & Mackay, $68

This denim shirt shares some of the upscale details with our grail-worthy Taylor Stitch western shirt but at about half the price. See how to wear a denim shirt here and here and here.

image of a white and brown stripe linen shirt

Linen Cotton Oxford Shirt

Spier & Mackay, $68

I’ve got my eye on brown striped dress shirts: It seems like lots of well-dressed guys in my digital orbit are rocking them with great effect.

image of a short sleeve blue and white polo style shirt

Moisture Wicking Performance Zip Polo

Express, $54

Generally hate polos because you feel like a guy wearing a retail uniform? Break out of the ordinary with a bold stripe.

image of a close up of a green sweater polo

Sweater Polo

Bonobos, $99

The knit polo is one of my favorite ways to dress casually while still looking like I have my -ish together. This option from Bonobos has a subtle and varying pattern for look that seems right out of The Rock’s playbook.

image of charcoal grey pant

All Week Flex Pant

Bonobos, $49 $119

For the man who has to wear pants BUT ISN’t HAPPY ABOUT IT.

image of a dark blue quilted jacket

The Quilted Jacket

Bonobos, $69 $229

I’ve owned several quilted jackets over the years and they always elevate a fall outfit. Classically rugged but more polished than your typical nylon winter jacket.

image of taupe brown slim fit pants

Stretch Cotton Chino

Suit Supply, $129

How do you keep the comfort of chinos while giving them a rakish European vibe for more dressed up outfits? Suit Supply’s Porto Chino features premium fabric with details like the extended tab closure for that effortless no-belt look.

image of a light brown long sleeve shirt

Merino Wool & Mongolian Cashmere Shirt

Suit Supply, $169

What do you get when you add a Johnny collar and raglan sleeves to a cashmere sweater? A drool-worthy pull you can wear anywhere except for the most formal of events.

image of brown canvas pants

Canvas Workwear Pants

Old Navy, $30.80 $49.99

A budget-friendly take on the OG-107 pant.

image of a navy blue curved hem short sleeve shirt

Slub Knit Curved Hem Shirt

Old Navy, $8.40 $14.99

Generally we have to sacrifice detail when shopping frugally, but Old Navy is offering a curved hem t-shirt with textured slub knit for less than $10.

image of a rugby style polo shirt

Rugby Polo Shirt

Old Navy, $30 $39.99

The 90s are back – the rugby shirt is one of the few things I have no complaints about.

image of a long sleeve black polo shirt

Uniqlo, $49.90

For a more wallet-saving option than the Bonobos and Suit Supply polos, this merino wool knit polo is the smart way to test the waters on the look.

image of a print long sleeve hoodie shirt

Bonfire Fleece Baja Hoodie

American Eagle, $59.95

A hoodie with detail.

levi's 501 light wash straight fit jeans

Levi’s 501 Jeans


For a guy who needs a straighter fit jean because he’s got that leg routine on lock or for the rest of us experimenting with a looser fit.

image of a white linen shirt

Linen-Blend Button Up Shirt

Abercrombie & Fitch, $33.60 $60

The camp collar shirt and the white linen shirt are two of our favorite summer styles.

image of a geometric pattern sweater short sleeve polo shirt

Johnny Collar Geometric Sweater Polo

Abercrombie & Fitch, $28 $50

Like the Chris Evans/The Gray Man retro polo style but not ready for vibrant patterns or colors? Here’s one that will fit right in with your work wardrobe capsule.

image of a blue plaid long sleeve shirt

Madras Plaid Mill Shirt

Alex Mill, $145

Alex Mill is the next step up if you love a classic J.Crew style.

image of black stretch jeans

Made in California Super Stretch 5-Pocket Denim Pant

Gustin, $81

Investing in quality clothing that supports American jobs doesn’t have to cost you hundreds of dollars. These deep black 5 pocket pants will look great in smart casual outfits and will look killer in casual outfits for years if they fade.

image of a cotton twill long sleeve shirt

Cotton Twill Blanket Shirt

Outerknown, $148

Equal parts your favorite flannel and shirt jacket, the beach-inspired blanket shirt from surf brand Outerknown will be your go-to this fall.

How to wear a shirt jacket:

image of a man wearing a short sleeve shirt

Slub Curved Hem Tee

Buck Mason, $42

Buck Mason is a brand that pays attention to the details in its reviving of classic and long-standing men’s essentials. Their “Venice Wash” combines a natural enzyme rinse with small batch dying to create distinctive but subtle color variations.

image of a black leather jacket

Bruiser PCH Jacket

Buck Mason, $548

Buck Mason’s new PCH jacket has a design reminiscent of my 1940s California motorcycle jacket.

image of charcoal grey herringbone pants

The Easy Pant

Taylor Stitch, $128

The Easy Pant features a charcoal herringbone pattern and an elastic waistband – the result is a refined but still mega-comfortable pant that can easily cross casual-dressy boundaries.

image of a dark brown oxford long sleeve shirt

The Jack Oxford Shirt

Taylor Stitch, $125

A subtle brick-red organic oxford cotton with a tailored armhole and shorter fit to be worn untucked, Taylor Stitch’s Jack Oxford is an upgrade that makes perfect sense.

image of a red shawl collar sweater

Checker Stitch Shawl Cardigan Sweater

J.Crew, $138

Branch out of neutrals with this deep red shawl collar collar cardigan. It’ll be a sharp layer for the end of summer and be your favorite hoodie alternative all of fall.

image of light tan suede clog shoes

Birkenstock Boston clogs

J.Crew, $145

One of our top summer shoes for guys who don’t wear sandals, the Birkenstock Boston also works surpassingly well in cooler weather also, with many-a-well-dressed guys wearing them with intricately patterned, textured socks.

image of a green corduroy ball cap hat

Corduroy Baseball Cap

J.Crew, $39.99 $49.50

Those who say baseball caps have no place in a well-dressed man’s wardrobe have over-corrected. A refined pull like this emerald green corduroy cap is a simple piece with a lot of sharp details.

image of a blue and white striped long sleeve shirt

Organic Cotton Oxford Shirt

J.Crew, $44.99 $79.50

Multiple widths on the stripes give this OCBD unique character.

image of a blue short sleeve shirt

Camp Collar Harbor Shirt

J.Crew, $48.99 $69.50

Take a t-shirt, give it buttons and pockets, and equip it with a camp collar, and what’ve you got? The lazy man’s secret style weapon.

image of a long sleeve button up white corduroy shirt

Cuisse de Grenouille Corduroy Overshirt

Wittmore, $200

Made in Portugal and designed in Paris, this corduroy overshirt is like a light light jacket.

image of white and navy knit shoes

The Royale Knit

Greats, $119

These are one of my go-tos when I don’t want to think about what to wear. They’re machine washable, and their minimalist design works with refined summer or fall outfits effortlessly.

image of blue and white sneaker shoe

Classic Nylon Sneakers

Reebok, $70

Paired with some cuffed Levi’s 501, these classic Reeboks are as comfortable as they intentional.

image of brown and white suede sneaker shoe

Era Pig Suede Sneakers

Vans, $70

Upgrade your favorite Vans to pig suede for a look that is more startup boardroom than beach boardwalk.

image of a white high top sneaker shoe

Chuck 70 Tonal Leather Sneaker

Converse, $95

An all-white leather version of my fav parchment Converse Chuck 70s.

image of moc toe style boot shoes

Diplomat Moc Toe Shoe

Thursday, $199

I’ve had my eye on the Dipolmats for years – they’re a lower profile version of the classic moc toe work boot, making them easier to wear in more smart casual outfits.

image of a slip on loafer shoe

Scarsdale Slip On Loafer

Allen Edmonds, $119.97 $195

A sap brown suede version of the loafer we featured in our What to Wear to Work When It’s Hot Capsule Wardrobe – and now it’s on sale.

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