Jumpstart Your Fall Style With These 38 Picks

Jumpstart Your Fall Style With These 38 Picks
What we're looking forward to this autumn.

Yes, it’s still hot outside, but fall is nearly here, and it’s time to gear up. This fall is all about sartorial simplicity mated to functionality. Soft, warm, rugged fabrics, earth tones, and understated flare (yes, there is such a thing) will keep you looking good, and just as importantly, feeling good.

The days of going to the mall and spending four hours trying to revamp your seasonal wardrobe are gone. We’ve scoured the internet and found the latest fall pieces that hit every budget, and pair value with classic style.

If your fall closet could use an update, take a look at our top picks below:

Slim marled cotton shirt

Slim Marled-Cotton Shirt

J.Crew Factory $34.50

With a linen texture and a marled design, this cotton shirt is somehow a statement piece that’s still subtle. Want to tone it down a bit? Layer it under a sweater.

Brushed Twill Pants in Skinny Fit with GapFlex

Brushed Twill Pants in Skinny Fit

Gap, $69.95

Brushed cotton with GapFlex technology means you’ll be comfortable while still looking professional. And the charcoal color will pretty much match everything you own.

Everyday cashmere crewneck sweater in multicolor stripe

Cashmere Crewneck Sweater in Multicolor stripe

J.Crew, $128

This sweater is beautiful. J.Crew has several decades in the cashmere game, and they’ve got it dialed in pretty well. Lightweight, but still soft and warm; that’s the perfect cashmere sweater. J.Crew has also teamed up with the Sustainable Fibre Alliance, a group dedicated to maintaining ethical and sustainable practices in the sourcing of cashmere.

Navi Ocean

Timex Navi Ocean Watch

Huckberry, $155

Stainless steel, reversible nylon strap, and a hardened glass crystal mean this easy-to-read watch can take a beating. This watch is perfect for casual fall wear, and it’s classic 38mm size can just peak out under your cuff to make a statement without being ostentatious.

The Yosemite Shirt in British Khaki

Yosemite Shirt in British Khaki

Taylor Stitch, $98

The contrast of the white buttons complements the soft, brushed flannel texture of this chamois shirt. Ultra strong, and smoother than silk, this is the perfect fall shirt to throw on with a pair of dark denim.

Fossil Men Townsman Stainless Steel and Leather Casual Quartz Watch

Fossil Townsman Stainless Steel Leather Strap Watch

Amazon, $75.99

They call it casual, but this watch could pass at the office as well. With a quartz movement (which is the most accurate movement you can buy at a decent price point), stainless case, and blue face with gold hands, this watch is timeless (sorry…I couldn’t resist).

Rugby crewneck shirt in pieced stripe

Rugby Striped Crewneck Shirt

J.Crew, $69.50

J.Crew went out on a limb and created a shirt we didn’t even know we wanted. This rugby shirt chops off the collar for a more laid-back aesthetic while maintaining the softness and strength of cotton jersey fabric.

Hemp Chambray Work Shirt

Hemp Chambray Work Shirt

Huckberry, $88

With coated metal buttons and a hemp-blend fabric, this shirt strikes the perfect balance between workhorse and comfortable. And not only is hemp strong, it’s also antibacterial, which helps fights odor when you start to work up a sweat. And no, you can’t smoke it.

Textured cotton crewneck sweater

Textured Cotton Crewneck Sweater

J.Crew Factory, $29.99

Layer this over a button-up shirt with some chinos, or wear it over a t-shirt with denim and a pair of suede chukkas. This sweater is light, versatile, and has a slim cut.

Felted Chore Coat

Felted Chore Coat

Buck Mason, $195

This coat has been boiled twice, aerating the fabric to give it better insulating properties than traditional merino wool. It comes in multiple colors and has a cut that’s perfect for fall layering.

Shawl Cardigan Sweater

Shawl Cardigan Sweater

Gap, $70

This cardigan is cut with a generous fit for layering over your favorite long-sleeved t-shirt or button up. It will keep you warm, and the shaker stitch (think old-school knitting) will make sure it holds its shape.
FRYE Men's Bowery Chelsea Boot

FRYE Bowery Chelsea Boot

Amazon, $276.79

With Goodyear welt construction and military styling, these will stand the test of time in both style and durability.

Walker vest

Walker Vest

J.Crew, $55.50

This imponderous vest is just right to keep the fall wind off your chest without restricting your movement or making you feel like you’re wearing a life-preserver. See how to wear it in our Reader Getup with Khoi from Gentleman Within.

The Fisherman Sweater in Natural Waffle

Fisherman’s Sweater in Waffle Weave

Taylor Stitch, $178

Taylor Stitch created a lightweight wool blend that gives you the texture of a fisherman’s sweater without making you sweat within ten minutes of putting it on. It’s soft, it breathes, and it looks damn good.

Neppy twill shirt

Neppy Twill Shirt

J.Crew, $75

Brushed twill for softness, with a cotton-poly blend for strength. This shirt comes in four different fits and six handsome colors. And if you’re like me, you want them all.

The Air Chino

Lightweight Air Chino

Everlane $58

This summer weight chino is constructed from a poplin cotton with 4% elastane for stretch and comfort. Great for those first few weeks of fall when it’s not quite cool enough yet for wool pants.

Slim Wool Blend Knit Blazer

Slim Wool Blend Knit Blazer

Banana Republic, $298

This blazer looks just as at-home with a pair of jeans as it does with a pair of dress slacks. Brushed, jacquard fabric has a pattern that is woven in instead of merely printed.

Amazon Brand   Goodthreads Men's "The Perfect Oxford Shirt" Slim Fit Long Sleeve Solid

Goodthreads Slim-Fit Oxford Shirt

Amazon, $24.37

Amazon’s tumbled oxford cotton is soft yet sturdy, and at this price point, you may as well get a few of them.

Cotton Textured Shirt in Maroon

Cotton Textured Shirt

Frank and Oak, $59.50

Who says a cotton shirt has to be boring? With horn buttons and a texture that goes one step above oxford cloth, this classic-fit shirt will take you into fall with style.

Raglan Bomber Jacket

Raglan Bomber Jacket

Gap, $100

With a nylon woven shell and a quilted lining, this lightweight bomber will keep the wind out without letting you get overheated.


Long sleeve broken in henley

Long Sleeve Broken-In Henley

J.Crew Factory $19.95

Like a pair of penny loafers the henley will never go out of style. Grab one of these in sage green, and throw it on with your favorite pair of denim and some casual sneakers. You’re all set.


Cole Haan Men's Wagner Grand Penny Loafer

Cole Haan Wagner Grand Penny Loafer

Amazon, $73.84-289.11

While they also sell women’s shoes, bags, coats, and accessories, Cole Haan originally started as a men’s shoe company, and loafers were their bread and butter. The bourbon suede is perfect for fall, and the rubber soles will give you the grip and longevity you need.

Flight Jacket

Flight Jacket by Flint and Tinder

Huckberry, $198

Flint and Tinder modeled this jacket after vintage Air Force issue jackets worn by famous pilots and astronauts. Made in the USA from lightweight cotton, this jacket is the perfect transition piece into fall.

Soft Wear Slim Jeans with GapFlex

Soft Wear Slim Jeans

Gap, $79.95

These cotton-poly blend jeans bring the ultimate comfort with stretch and softness. Cut slim, not skinny, the fit is form-fitting without being snug.


warby parker bryon eyeglasses

Bryon Eyeglasses in Aegean Blue Fade

Warby Parker, $95

With a subtly arched browline, and a bit of flare with the Aegean blue, these acetate frames are daring.

mott & bow slim leroy jeans

Slim Leroy Denim

Mott and Bow, $128

No, you’ve never owned jeans this soft. Mott and Bow wash the fabric several times over the course of a few months, and that’s between sanding it and stone washing it as well.

Seiko Men's Silvertone Stainless Steel Automatic Watch

Seiko Silvertone Stainless Automatic Watch

Amazon, $113.99

Seiko has been around since 1881 and has become synonymous with bang for your buck watches. Automatic movement, stainless steel casing, and a black and green face. No one else at the office will have this timepiece, and you won’t have to go broke to own it.
Wolverine Men's 1000 Mile Fashion Boot

Wolverine 1000 Mile Boot

Amazon, $339.95

When we talk about classic men’s work boots, two names come to mind: Redwing and Wolverine. These boots are for the garage when it’s time for a brake job, but they’re also for a trip to the pub with your buddies once the job is done.

Slub Cotton Raglan Crewneck Sweater

Cotton Raglan Crewneck Sweater

Gap, $50

The slub knit cotton has a casual drape that’s satisfying against the skin while keeping you warm. We like the dark olive and the oatmeal: solid earth tones, which complement any fall wardrobe.

Slim fit flex chino

Slim-Fit Flex Chino

J.Crew Factory, $29.50-34.99

These are available in any color you want (and a few you didn’t realize you wanted). Perfect for work or a night out with your lady, these cotton chinos have a hint of stretch for mobility and the perfect slim cut.

Mens Leather Bomber Jacket In Black

Leather Bomber Jacket in Black

DSTLD, $350

This lambskin leather bomber has been coated to protect against stains yet still maintains its soft, broken-in feel. It’s fully lined with two interior pockets to stash your phone and cinnamon gum.

Slim Fit Cords with GapFlex

Slim Cut Cords

Gap, $69.95

Thin wale cords with a slim silhouette. They’re corduroys: wear them to work, wear them on a date, wear them on the couch.

Slim American Pima cotton oxford shirt with mechanical stretch in plaid

American Pima Cotton Slim Plaid Shirt

J.Crew, $69.50

Through their own blend of sartorial magic, J.Crew has created a stretch cotton without actually adding any stretch material. I know. They’re amazing.

Levi's Men's Standard Barstow Denim Western Snap Up Shirt

Levi’s Western Denim Snap-Up Shirt

Amazon, $34.99

This western style shirt has an updated fit but maintains the ruggedness that we’ve come to associate with Levi’s denim. Giddy up.

Amazon Brand   Goodthreads Men's Standard Fit Long Sleeve Plaid Herringbone Shirt

Goodthreads Plaid Herringbone Shirt

Amazon, $30.00

This classic plaid is highlighted by the subtle herringbone pattern and excellent color combinations. Be sure to check out the navy eclipse and the Green shadow plaid.

Slim fit Thompson suit jacket in Donegal wool

Slim-Fit Suit Jacket in Donegal Wool

J.Crew Factory, $190.00

Donegal wool is named after the area in Ireland where the wool was originally made. It’s flecked, warm, and cozy. J.Crew Factory has made this jacket in a Donegal blend to keep the weight down and the softness up.

Slim fit Thompson suit pant in Donegal wool

Slim-Fit Suit Pant in Donegal Wool

J.Crew Factory, $109.99

If you’re getting the jacket, you can’t skip the pants.

Mike Henson

Mike Henson is a literature teacher in Hershey, Pennsylvania. He enjoys shooting 35mm film, restoring vintage straight blades, purchasing too many American-made goods, and spending time with his wife and their three daughters.