There is a very specific moment every October when a man opens his closet, stares at nine nearly identical T-shirts and a hoodie he's owned since college, and realizes summer was covering for him. The weather changed. The wardrobe didn't. And no, the quarter-zip from your company retreat does not count as a personality.
So for Cohesive's first men's fall issue, I went to someone who dresses men for a living. Dina Cerchione has spent more than 30 years styling celebrities and reality TV guests, with costume design credits on America's Got Talent and Deal or No Deal, and she personally styles Howie Mandel. She does a lot of it on network TV budgets, which means she knows how to make a regular guy look camera-ready without a celebrity's bank account. Her first rule? "What you're wearing has to be done with intention."
To keep things honest, I scored every piece on four things Dina kept coming back to: Price, Versatility (can it go to the football game and the dinner after?), Staying Power (will it look dated in two years?), and Fall Factor (texture, weight, color, the stuff that makes October feel like October). Each gets a score from 1 to 5, for a total out of 20. Then I ranked them inside their categories, because comparing a loafer to a sweater is like comparing a dog to a sandwich.
Jackets
1. Levi's Vintage Faux Cow Suede Trucker Jacket, $139.95
Recommended for: The guy who owns exactly one jacket and wants it to be the right one.
The stylist's take: This was the first thing out of Dina's mouth when I asked what never goes out of style. "It's like, what, Levi's brought them in in the 1800s? I don't even know when they started, right?" she laughed. "It's never going to go out of style. So spend the money on it." This version lists at $139.95 and was marked down to $97.97 when we checked, so you can test her theory before going full suede.
Scoring: Price, 4/5; Versatility, 5/5; Staying Power, 5/5; Fall Factor, 3.5/5 (faux suede, so it won't age like the real thing)
Total Score: 17.5/20
2. Merci Dema Night Shift Workman Jacket, $255
Recommended for: Men who want their clothes to mean something.
The stylist's take: Dina's biggest rule is that you start with the person, because "if you don't feel like you, it's going to feel like a costume." Merci Dema founder Melly Adkins clearly agrees. He left a career in law after burning out and now calls his label "vulnerable luxury." The name combines "thank you" and "tears" from two different languages. The workman jacket is $255; layer the $70 "We All Cry" tee underneath if you're feeling brave.
Scoring: Price, 2.5/5; Versatility, 3.5/5; Staying Power, 4/5; Fall Factor, 4/5
Total Score: 14/20
Shoes
3. Hockerty Penny Loafers in Brown Suede, $231
Recommended for: Men whose feet have never fit anything off the shelf, which is most of us.
The stylist's take: Suede loafers were on Dina's fall list, and her feelings on fit are not subtle: "It's all in the tailoring." Most men have never experienced that with shoes. Hockerty, a Swiss bespoke brand with more than 15 years in the business, doesn't make your pair until you order it. Then artisan shoemakers in Almansa, Spain build it by hand from leather sourced from Spanish and Italian tanneries, through more than 50 steps, in US sizes 3 to 16, including special widths. The price is $231, about what you'd pay for a mass-produced designer loafer that was sitting in a warehouse before you were born. (Fine, before last Tuesday.)
So what does it feel like to own a pair of handmade Spanish shoes? Let's start with the box. There's a smell that hits you first, warm and a little sweet, the smell of leather that hasn't been sitting under fluorescent lights for a season. The suede has a soft nap that shifts color when you run your thumb across it, darker one way and lighter the other. They're built on a last with a rounded toe and extra room across the front, so your toes aren't fighting for space at a dinner that runs long. And the shoes are designed to look better and feel more comfortable the longer you wear them. Give it two weeks and the heel stops feeling new and starts feeling like yours. That's what made-to-order really means: someone built this shoe for one foot, and that foot is yours.
This is the shoe Dina's whole fall philosophy comes back to. Wear it with dark jeans and the merino crew to dinner, or with trousers and an unstructured blazer to the office. Brown suede is the most fall thing a man can put on his feet. [ADD YOUR TEAM'S IMPRESSIONS OF THE PAIR HOCKERTY SENT.]
Scoring: Price, 3.5/5 (custom, for less than a lot of off-the-rack designer loafers); Versatility, 5/5; Staying Power, 4.5/5; Fall Factor, 5/5
Total Score: 18/20
4. Gucci Horsebit 1953 Loafers, €750
Recommended for: Men ready to buy one pair of shoes for the next 20 years.
The stylist's take: Dina warned against the chunky trend versions of loafers. Her pick is the original: "the classic horsebit loafer from Gucci that's been around forever. It's not going anywhere." Mytheresa lists it at €750. That's a lot. It's also cheaper per wear than the six pairs of sneakers you'll replace before it gives out.
Scoring: Price, 1/5; Versatility, 4.5/5; Staying Power, 5/5; Fall Factor, 3.5/5
Total Score: 14/20
5. Hockerty Boots in Brown Suede, $285
Recommended for: The days your loafers can't handle the weather.
The stylist's take: Same Spanish workshop, more ankle. At $285, it's the pair you'll reach for once the leaves turn into slush. Dina's rule about texture applies here too: brown suede on a boot reads warm in a way smooth black leather never will.
Scoring: Price, 3/5; Versatility, 3.5/5; Staying Power, 4.5/5; Fall Factor, 5/5
Total Score: 16/20
Shirts & Knits
6. Uniqlo Merino Sweater, $49.90
Recommended for: Everyone. Literally.
The stylist's take: "I love a thin knit crew neck for people," Dina said. "You can wear it on its own. You can wear it over a T-shirt. You can wear it under a blazer. You can do so many things with it." It's $49.90 on Uniqlo's US site, which is less than most men spend on a bar tab they don't remember. Buy it in navy and charcoal and stop thinking about it.
Scoring: Price, 5/5; Versatility, 5/5; Staying Power, 4.5/5; Fall Factor, 4/5 (thin, so you'll want a jacket by November)
Total Score: 18.5/20
7. Taylor Stitch The Maritime Shirt Jacket, $208
Recommended for: Men with two very different Saturdays.
The stylist's take: Dina is obsessed with the overshirt, and honestly, now so am I. Her logic is that the fabric decides where it can go: a heavy plaid "is going to take you on your casual days, when you're going to see football games and all the things," while a suede one gets you into a dinner or an office. This burgundy plaid wool version retails for $208.
Scoring: Price, 3/5; Versatility, 4/5; Staying Power, 4/5; Fall Factor, 5/5 (it basically smells like a bonfire)
Total Score: 16/20
8. Taylor Stitch The Newton Sweater Polo in Dried Cherry Merino, $178
Recommended for: The plans that are too nice for a T-shirt and too relaxed for a tie.
The stylist's take: Dina called this the "in between thing," and it's where most men fall apart. Her fix: "I love, like, a long sleeve polo." This one is $178 and comes in a deep cherry that looks like it was invented for October. Wear it to a dinner where you're meeting someone's parents.
Scoring: Price, 3/5; Versatility, 4/5; Staying Power, 3.5/5 (the color is a commitment); Fall Factor, 5/5
Total Score: 15.5/20
Denim
9. Levi's 501 Original Jeans, Dark Wash, $98
Recommended for: Anyone still wearing light-wash jeans in November (we see you).
The stylist's take: "Dark, dark wash jeans, you can dress them up, you can dress them down," Dina said. "I think that's a key for fall." The 501 in a dark wash lists at $98 and was on sale for $55.98 when we checked. Yes, these are the same jeans your dad wore in every photo from 1994. He was right about this one thing.
Scoring: Price, 4/5; Versatility, 5/5; Staying Power, 5/5; Fall Factor, 3/5
Total Score: 17/20
Glasses
Dina doesn't follow strict color theory, but she watches faces closely. Some colors make "my face feel a little brighter," she said, while others make it look "more sallow." Lens tints work the same way, and since the October sun sits low enough to hit you right in the eyes on the drive home, fall is when your sunglasses matter most. All three of our picks come from FORK, a brand that says it was born on club floors at 4 a.m., and every pair has UV400 protection and a backside anti-reflective coating.
10. FORK SLOW BURN, $110
Recommended for: The guy who wants one pair that does everything.
The stylist's take: An oversized square acetate frame for $110, and every frame color comes with a choice of lighter or darker lenses, so you can match the tint to your skin the way Dina would. It also arrives with an aluminum case, which is more than you can say for the gas station pair in your glovebox. Pair the brown frame with the suede trucker and you're done.
Scoring: Price, 3.5/5; Versatility, 4.5/5; Staying Power, 4/5; Fall Factor, 4.5/5
Total Score: 16.5/20
11. FORK 04AM, $95
Recommended for: Men who want something a little louder.
The stylist's take: The 04AM is $95, in colorways that include tortoise with green lenses and orange with gray. Go tortoise. It's the most autumn color combination in eyewear, and it warms up a face that summer left pale.
Scoring: Price, 4/5; Versatility, 3.5/5; Staying Power, 3.5/5; Fall Factor, 4.5/5
Total Score: 15.5/20
12. FORK CUTOFF, $95
Recommended for: The minimalist who owns more gray sweaters than he'd admit.
The stylist's take: An angular, square-leaning metal frame with a double rim, for $95. It's sharp and low-key, and silver with a charcoal knit is the move. It loses a few points on Fall Factor only because metal reads cooler than acetate once the leaves turn.
Scoring: Price, 4/5; Versatility, 4/5; Staying Power, 4/5; Fall Factor, 3/5
Total Score: 15/20
My big takeaway is that the cheapest thing on this list won overall, which is exactly what Dina predicted. When I asked whether men need money to dress well, she didn't hesitate: "Oh hell no." But the piece I can't stop thinking about is the Hockerty loafer, a shoe made for one foot by someone in Spain who never met you. Start with a $49.90 sweater. Then put your money where you'll feel it every single day.
Follow Dina at @dmcstyles.
