Jake Woolf

Jake Woolf

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Menswear writer/creator; product and trend analysis; runs a menswear Substack.

Fisherman Sandals Are Back—My Top Picks Revealed
SocialApr 8, 2026

Fisherman Sandals Are Back—My Top Picks Revealed

Fisherman sandal season is rapidly approaching—it’s time to hop aboard and reel in a pair Wrote about why these style shoes are lovely, why my favorite pair is my favorite and 4 more awesome pairs Link in bio https://t.co/WqkYY4w660

By Jake Woolf
Orslow 105 Jeans: Vintage Levi’s Feel, $300 Price
SocialApr 8, 2026

Orslow 105 Jeans: Vintage Levi’s Feel, $300 Price

There’s nothing on earth like a pair of well worn vintage Levi’s But these Orslow 105 jeans are the closest thing on the market to the originals, AND are way easier to buy Question is: are they worth the $300...

By Jake Woolf
Japan vs USA 90s Denim Wash Showdown
SocialApr 7, 2026

Japan vs USA 90s Denim Wash Showdown

Orslow made in Japan 105 in 90s sky blue wash 90s made in USA Levi’s 501 in “being 30 years old” wash Full comparison coming soon https://t.co/gSv9fVbTfx

By Jake Woolf
Maturity: Shopping without the SSENSE UI Hassle
SocialApr 6, 2026

Maturity: Shopping without the SSENSE UI Hassle

maturing is realizing you can buy clothes without ever having to subject yourself to the UI of SSENSE dot com

By Jake Woolf
Desert Boot Renaissance Sparks Nostalgic Style Optimism
SocialApr 5, 2026

Desert Boot Renaissance Sparks Nostalgic Style Optimism

The desert bootaissance is coming… I’ve been rocking this pair for a few weeks now, and feeling a stylistic optimism that reminds me of a time when buying a bottle green baracuta jacket at the jcrew liquor store in 2009 was...

By Jake Woolf
Desert Boots, Loafers, Dad Sneakers: Spring’s Essential Trio
SocialApr 4, 2026

Desert Boots, Loafers, Dad Sneakers: Spring’s Essential Trio

Desert boots, loafers, dad sneakers: the holy trinity of spring shoes that you can survive the entire season with https://t.co/Mat7wYajSu

By Jake Woolf
Caught Buying $500 Loafers, Pretending It
SocialApr 4, 2026

Caught Buying $500 Loafers, Pretending It

me when my gf asks who I was on the phone with (it was the shoe store telling them to run my card for a new pair of $500 loafers) https://t.co/FM7G4vM6SZ

By Jake Woolf
Ralph Lauren Bi‑Swing Jacket Crowned Spring’s Top Pick
SocialApr 3, 2026

Ralph Lauren Bi‑Swing Jacket Crowned Spring’s Top Pick

As I’ve been saying, the Ralph Lauren bi-swing jacket is the best spring jacket of all time Clearly ALD agrees since they just dropped their take which I really like particularly in red. Also into this khaki jacket / denim...

By Jake Woolf
Italian Burgundy Loafers: Blu Scarpa X Jake Woolf
SocialApr 3, 2026

Italian Burgundy Loafers: Blu Scarpa X Jake Woolf

Oh—you want loafers in the most classic shape and lovely, soft deep burgundy leather that you can wear with everything all year round? That are made in Italy? Got you. Blu Scarpa x Jake Woolf. Coming soon. https://t.co/kvQNAvmoNy

By Jake Woolf
Nostalgic Tribute: Seeking Ralph Lauren Version of Iconic Coat
SocialApr 3, 2026

Nostalgic Tribute: Seeking Ralph Lauren Version of Iconic Coat

I’ve always loved this photo of the late great Glenn Obrien (who was one of the first people I ever interviewed for Hypebeast when I was 20 years old) in his John Pearse black watch trench coat I just found...

By Jake Woolf
Only Two Vintage Armani Tags Worth Recognizing, Emporio Separate
SocialApr 3, 2026

Only Two Vintage Armani Tags Worth Recognizing, Emporio Separate

The only two vintage Armani tags we acknowledge emporio too but that’s kind of a different thing in my mind https://t.co/AY9ULqNPvZ

By Jake Woolf
Rare Armani Black Label Suits Land at Williamsburg Vintage Store
SocialApr 1, 2026

Rare Armani Black Label Suits Land at Williamsburg Vintage Store

🚨 IMPORTANT 🚨 A new grip of Armani black label suits fresh from the closet of a retired Long Island hedge fund manager have arrived at Williamsburg’s greatest vintage store for suits, Ebreo https://t.co/dKk6ICLsZw

By Jake Woolf
Spotting Luxe Sweatshirts: Red Silk Blend & Vintage Gold
SocialApr 1, 2026

Spotting Luxe Sweatshirts: Red Silk Blend & Vintage Gold

Two very good sweatshirts I spotted at Ven Space One a cotton wool silk blend from Auralee. Super lightweight and luxurious feeling. Big fan of red sweatshirts Another a vintage style crewneck in a gorgeous golden brown hue from A.Presse...

By Jake Woolf
18East Leads Pants Innovation with New Seasonal Styles
SocialApr 1, 2026

18East Leads Pants Innovation with New Seasonal Styles

There might not be a better brand on planet earth at making pants than 18East So I stopped by the store to chat through a bunch of new styles the label is making this season with founder Antonio Ciongoli https://t.co/Uoq5Lc0K8G

By Jake Woolf
Friends' Bewildered Faces After 20 Minutes of Niche Talk
SocialMar 31, 2026

Friends' Bewildered Faces After 20 Minutes of Niche Talk

My normie friends after I’ve been talking for 20 minutes straight about Stoffa, Comoli, and A.Presse https://t.co/GcetnjZGYs

By Jake Woolf
Company Ignored Sneaker Craze, Stuck with Bland Knits
SocialMar 31, 2026

Company Ignored Sneaker Craze, Stuck with Bland Knits

For 5 years this company saw everyone getting rich off of dad sneakers and fun technical runners and tripled down on minimal, soulless, knit upper slop not shocked at this development

By Jake Woolf
Multiple Rings Fine, Brooklyn Men Feel Like Fork Stabs
SocialMar 30, 2026

Multiple Rings Fine, Brooklyn Men Feel Like Fork Stabs

look, there’s nothing inherently wrong with the whole multiple rings trend but every time I shake hands with a dude who lives in Brooklyn it’s like getting stabbed with a fork

By Jake Woolf
2006 Lexus GX
SocialMar 30, 2026

2006 Lexus GX

All this fit is missing is the keys to a 2006 Lexus GX470 with 158,000 miles and perfect service records https://t.co/myR6a2RcEe

By Jake Woolf
Vintage Ralph Lauren Collection Hits Williamsburg Sale Tonight
SocialMar 27, 2026

Vintage Ralph Lauren Collection Hits Williamsburg Sale Tonight

I’ve been amassing vintage Ralph Lauren grails—now, it’s finally time to sell them - 1988 sailing inspired crewneck - Made in USA suit - Made in USA Bi-Swing jacket - 2002 hand knit eagle sweater & lots more Available tn...

By Jake Woolf
RRL West Broadway Offers Legendary Vintage Finds Worth Every Dollar
SocialMar 25, 2026

RRL West Broadway Offers Legendary Vintage Finds Worth Every Dollar

The vintage duration at RRL is truly next level. The prices are commensurate with the quality of the items, but it’s always just a treat to hit up the west broadway store and see so much legendary old product under...

By Jake Woolf
EBay Assassin Drops Rare Vintage Streetwear Finds
SocialMar 24, 2026

EBay Assassin Drops Rare Vintage Streetwear Finds

The eBay assassin is back at it again Vintage polo country trucker jacket Vintage polo Pima cotton v neck Vintage Levi’s silvertab jeans Vintage Gucci croc loafers https://t.co/V1arDB39UA

By Jake Woolf
Cinch Loose-Waist Chinos for Classic Ralph Lauren Cool
SocialMar 24, 2026

Cinch Loose-Waist Chinos for Classic Ralph Lauren Cool

If there’s one thing you can learn from old Ralph Lauren ads, it’s that chinos which fit a little big in the waist and you cinch with a belt look sick as hell https://t.co/QJeWY6NXAd

By Jake Woolf
Aaron Levine Collection Returns on Mr Porter, Same-Day Delivery
SocialMar 23, 2026

Aaron Levine Collection Returns on Mr Porter, Same-Day Delivery

Big news today for fans of really nice high quality good looking regular clothes Aaron Levine’s eponymous collection is now available on Mr Porter A lot of the stuff that sold out on his site is available once again And...

By Jake Woolf
Crockett & Jones Harvard 2: Classic
SocialMar 22, 2026

Crockett & Jones Harvard 2: Classic

Zeroing in on the Crockett & Jones Harvard 2 Unlined ✅ Classic casual shape ✅ Rubber sole good for NYC ✅ Made in England w/ long shoemaking history ✅ Referenced on Succession ✅ Gonna go to the SoHo store tmrw to investigate IRL https://t.co/PBzq7A0A13

By Jake Woolf
Score: $48 Armani Coat Turns You Into A‑Lister
SocialMar 21, 2026

Score: $48 Armani Coat Turns You Into A‑Lister

This Armani Collezioni double breasted sport coat remains the best eBay pickup I’ve ever made $48 in 2021 and makes me feel like an A-lister at the airport in 1994 every time https://t.co/F2qlTpMV5B

By Jake Woolf
A Simple Pique Polo Is Spring’s Style Secret
SocialMar 21, 2026

A Simple Pique Polo Is Spring’s Style Secret

Ok but what if forgetting every other shirt exists and wearing a humble, long sleeve pique cotton polo was the key to spring style all along Wrote about why I’ll be wearing this shirt for the next forever Link in...

By Jake Woolf
Piqué Polos: The Timeless Spring Wardrobe Essential
SocialMar 21, 2026

Piqué Polos: The Timeless Spring Wardrobe Essential

Spring style take: Knit polos have been getting all the attention the last couple of years—I think it’s time we all remember that the humble piqué polo is truly peak I wrote about the one that’s clearly the best of all...

By Jake Woolf
Embrace 90s Handyman Vibe with Soft Heartthrob Style
SocialMar 20, 2026

Embrace 90s Handyman Vibe with Soft Heartthrob Style

Going for the full 90s handyman with a soft side heartthrob aesthetic 90s RRL flannel 90s jeans from Agolde 90s coded desert boots 90s as hell hair Cue iris by goo goo dolls https://t.co/YavMUlko3M

By Jake Woolf
Big Trench Coats: Spring’s Ultimate Style Cheat Code
SocialMar 20, 2026

Big Trench Coats: Spring’s Ultimate Style Cheat Code

Your reminder that a big ass trench coat is the ultimate spring style cheat code https://t.co/gXC7X0qKv8

By Jake Woolf
Master Sniper Finds Elite Vintage Ralph Lauren on eBay
SocialMar 18, 2026

Master Sniper Finds Elite Vintage Ralph Lauren on eBay

Not gonna lie—I am a god damn sniper when it comes to finding elite vintage Ralph Lauren on eBay https://t.co/JZpd49HgJ9

By Jake Woolf
Why Vintage Curved Watches Still Defy Wrist Shape
SocialMar 17, 2026

Why Vintage Curved Watches Still Defy Wrist Shape

Really into the idea of buying a vintage curved case watch. Specifically something rectangular and dressy Honestly don’t know why more watches aren’t shaped this way—which is to say, shaped like your actual wrist https://t.co/ShZQXPJiZ7

By Jake Woolf
Swapped $13k for Rare 1940s Pink Gold Rolex
SocialMar 16, 2026

Swapped $13k for Rare 1940s Pink Gold Rolex

I give a guy $13,000, he gives me this 1940s pink gold Rolex bubble back. Who says no? https://t.co/UoMrhnodCA

By Jake Woolf
Chalamet's Oscars Outfit Sparks Jaw‑Dropping First Impressions
SocialMar 16, 2026

Chalamet's Oscars Outfit Sparks Jaw‑Dropping First Impressions

My first thought when I saw the fit chalamet wore to pull up to the Oscars https://t.co/XBJEJJheVJ

By Jake Woolf
Three Distinct Luxury Icons: Patek, AP, Vintage Rolex
SocialMar 16, 2026

Three Distinct Luxury Icons: Patek, AP, Vintage Rolex

3 very cool and very different watches I saw today Medium size (37mm) Patek Philippe Nautilus in white gold AP Offshore with a kind of ridiculous but also kind of fire red dial Pristine condition 1940s pink gold Rolex bubble...

By Jake Woolf
Petition to Restock Ralph Lauren’s Big Shirt for OCBD Fit
SocialMar 15, 2026

Petition to Restock Ralph Lauren’s Big Shirt for OCBD Fit

starting the official petition for Ralph Lauren to restock The Big Shirt, which is exactly how your OCBDs should fit (loose, wide, flowing in the breeze) In the meantime lots of good vintage options (my blue vintage OCBD is my...

By Jake Woolf
Ralph Lauren Turns Functional Menswear Into Costume Identity
SocialMar 13, 2026

Ralph Lauren Turns Functional Menswear Into Costume Identity

I love Ralph Lauren, but sometimes I think about the impact the brand had on inverting its particular brand of clothes, and as a result, menswear in general, from items that enhance your life to more like costume pieces—you wear...

By Jake Woolf
Kith X New Balance 991: Subtle, Premium, Made in England
SocialMar 13, 2026

Kith X New Balance 991: Subtle, Premium, Made in England

Big New Balance 991 guy here reporting that the new Kith collab I just got is excellent Also not a big colorful sneaker guy, so appreciate the subtlety and focus on materials here over anything attention grabby Made in England is...

By Jake Woolf
Scored 80s Gucci Crocodile Loafers at 4% Retail Price
SocialMar 11, 2026

Scored 80s Gucci Crocodile Loafers at 4% Retail Price

My eBay skills remain unmatched Got these genuine crocodile Gucci loafers from probably the 80s for $200 For context, new crocodile horsebit Gucci loafers retail for $4700 https://t.co/IgswjdfZyp

By Jake Woolf
70°F NYC Kicks Off Blue Oxford, White Jeans Season
SocialMar 10, 2026

70°F NYC Kicks Off Blue Oxford, White Jeans Season

70 degrees in nyc means happy official start of blue oxford shirt and white jeans season to all who celebrate https://t.co/5LNrt4F5OI

By Jake Woolf
Butter Yellow Arctic Jacket Stands Out Despite Self‑Doubt
SocialMar 10, 2026

Butter Yellow Arctic Jacket Stands Out Despite Self‑Doubt

Fear Of God FW26—fantastic I think it’d look objectively bad on me but the butter yellow Arctic jacket is sensational Would wear the entire first look tho https://t.co/yWs9HTgmZg

By Jake Woolf
Spring's Hottest Trend: Dockside Relaxation in Sweatpants
SocialMar 10, 2026

Spring's Hottest Trend: Dockside Relaxation in Sweatpants

You need to be embracing CBS this season—and I’m not talking about NCIS Here’s why spring’s biggest trend might be boats, sweatpants, and kicking back dockside Link in bio https://t.co/6a7gPC1L6t

By Jake Woolf
The Timeless Spring Jacket: 21 Must‑Have Picks
SocialMar 10, 2026

The Timeless Spring Jacket: 21 Must‑Have Picks

The perfect spring jacket does exist—and it’s been around for 80 years Here’s why I think everyone needs one, and the 21 best versions I found on the market today Link in bio https://t.co/m70EbWOdRj

By Jake Woolf
Alligator Strap Elevates $1800 Ralph Lauren 888 Watch
SocialMar 10, 2026

Alligator Strap Elevates $1800 Ralph Lauren 888 Watch

Highly considering buying this Ralph Lauren 888 watch 32mm, and the watch is good but the alligator strap is what puts it over the top $1800 also feels reasonable for such a beautiful looking timepiece https://t.co/GGQPzc19H8

By Jake Woolf
Reviving Woodgrain: Audi Q7 Coastline Edition Shines
SocialMar 9, 2026

Reviving Woodgrain: Audi Q7 Coastline Edition Shines

Audi Q7 Coastline Edition 4 seater luxury SUV with a V12 and walnut wood trim everywhere including the trunk liner. Let this be the start of my official campaign to bring back woodgrain https://t.co/HgxnR3tpfP

By Jake Woolf
Top 11 Spring 2026 Shoe Trends Revealed
SocialMar 6, 2026

Top 11 Spring 2026 Shoe Trends Revealed

As America’s leading footwear trend expert, I took it upon myself to pinpoint the 11 shoe trends that should be on your radar for Spring 2026. I then also found my favorite versions of each to create the 36 best...

By Jake Woolf
Ralph Lauren's Womenswear Outshines the Menswear Hype
SocialMar 6, 2026

Ralph Lauren's Womenswear Outshines the Menswear Hype

Everyone lost their mind at the Ralph Lauren menswear show in January and yeah it was cool but the womenswear is roughly 20x better https://t.co/p7YKUN0R6S

By Jake Woolf
Ralph Lauren Denim Chore Jackets: Stylish, Solid Price
SocialMar 6, 2026

Ralph Lauren Denim Chore Jackets: Stylish, Solid Price

Very good denim chore jackets from Ralph Lauren this season, complete with the classic Polo Country tag Also a very solid, worth it price at $368 ($298 for the white) https://t.co/eaYhsmkBld https://t.co/pN6vqPhG9U

By Jake Woolf
Ackermann Reimagines Business Suit with Playful Contrast Collars
SocialMar 5, 2026

Ackermann Reimagines Business Suit with Playful Contrast Collars

Haider Ackermann was cooking with these contrast collar dress shirt and tie combos A genuinely fun riff on a business suit classic without being too literal https://t.co/sm92AqPlK6

By Jake Woolf