Jake Woolf

Jake Woolf

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

Ralph Lauren Now Mimicking Kapital's Patchwork Chinos
SocialMay 3, 2026

Ralph Lauren Now Mimicking Kapital's Patchwork Chinos

In one week I’ve been told our legacy invented western belts and kapital invented patchwork chinos meanwhile, this is the man who until 2 years ago was doing Ralph Lauren’s vintage sourcing (these are another pair of his chinos in...

By Jake Woolf
2026 Summer Calls for Luxe Soft‑Slipper Footwear
SocialMay 3, 2026

2026 Summer Calls for Luxe Soft‑Slipper Footwear

Mark my words: 2026 is going to be another soft slipper summer Refined enough to wear with a linen suit, comfortable enough to wear to the beach—the epitome of laid back warm weather luxury A few good ones: - The...

By Jake Woolf
Zara's Designer Collaboration: My Honest Try-On Review
SocialMay 3, 2026

Zara's Designer Collaboration: My Honest Try-On Review

Zara teamed up with one of the most well known designers in menswear, so I went to the store to try it all on I loved some, didn’t care for some, but all of my thoughts available at the link...

By Jake Woolf
This Week's Top 5 Must-Have Style Picks
SocialMay 2, 2026

This Week's Top 5 Must-Have Style Picks

Here are my top 5 style recs of the week Including - a great casual spring suit - the only camp collar shirt I endorse - ass shoes - a review of almost everything from Aaron Levine x Zara Link in...

By Jake Woolf
Aaron Levine X Zara: What’s Worth Buying
SocialMay 2, 2026

Aaron Levine X Zara: What’s Worth Buying

Mall brand whisperer Aaron Levine just released his latest collection with Zara, so I went to the store on a mission to try on basically everything Some of it is amazing, some I didn’t love, but here’s my thoughts...

By Jake Woolf
Top Loafer Picks: Alden, Gucci, Row, More
SocialApr 30, 2026

Top Loafer Picks: Alden, Gucci, Row, More

Loafer lineup-off. Drop your rotations kings Clockwise Alden 684 Crockett & Jones Harvard 2 The Row soft loafers Vintage Gucci croc skin Jake Woolf x Blu Scarpa crocskin la college loafer Alden 986 https://t.co/BbPrdttcIG

By Jake Woolf
Loose, Pleated Shorts Just Above Knee Are Ideal
SocialApr 29, 2026

Loose, Pleated Shorts Just Above Knee Are Ideal

LETS TALK SHORTS: IMO they should fit loose (why anyone would want a slim fit short is beyond me) and I personally love a pleat. Length wise, just above the knee is ideal. Here are 4 great pairs - Aaron...

By Jake Woolf
Seiji McCarthy Declares My Shell Cordovan Loafers Perfect
SocialApr 28, 2026

Seiji McCarthy Declares My Shell Cordovan Loafers Perfect

Thought my shell cordovan color 8 Alden loafers were cool until I was on Instagram and got absolutely bespokemogged by Seiji McCarthy Dear lord these are perfect https://t.co/XNukkxJCrf

By Jake Woolf
Ralph Lauren Ricky Pant: New Women’s Take on OG‑107
SocialApr 26, 2026

Ralph Lauren Ricky Pant: New Women’s Take on OG‑107

No shortage of OG-107 reproductions on the market, but I’m intrigued by the Ralph Lauren women’s version called the Ricky pant. 11.5 inch rise, 8” leg opening, nice worn in cotton sateen fabric. Might have to try out a size...

By Jake Woolf
Choosing Between Black or Burgundy Alden 684
SocialApr 26, 2026

Choosing Between Black or Burgundy Alden 684

Harnessing the power of the timeline here: which Alden 684 should I get: black or color 8 (burgundy) ? https://t.co/kKOvkS22jx

By Jake Woolf
Expensive Loafers Spark Street Curiosity
SocialApr 26, 2026

Expensive Loafers Spark Street Curiosity

Wore $900 loafers and someone on the street asked l where I got em https://t.co/jhZX0V5KfS

By Jake Woolf
Supreme's Underrated Gingham Trench: Timeless Sophistication
SocialApr 26, 2026

Supreme's Underrated Gingham Trench: Timeless Sophistication

One of the most underrated Supreme collaborations ever—subtle, sophisticated, and genuinely timeless Still want the gingham trench https://t.co/MmjveNiipd

By Jake Woolf
Retro Vibes: Modern Outfit Mirrors 1988 Banana Republic
SocialApr 25, 2026

Retro Vibes: Modern Outfit Mirrors 1988 Banana Republic

Not wearing any Banana Republic but this feels like the kind of fits they were deploying in ads in 1988 https://t.co/nkdLDSkgjT

By Jake Woolf
Bare Knuckles Launches First NYC Pop‑up Shop
SocialApr 24, 2026

Bare Knuckles Launches First NYC Pop‑up Shop

One of my favorite independent brands, Bare Knuckles, just opened its first ever popup shop in NYC It’s open all weekend so I went by to check it out Stop by to support the homies https://t.co/MdYvwOtIkY

By Jake Woolf
Stone Island Revamps Classic Jacket in Six New Fabrics
SocialApr 22, 2026

Stone Island Revamps Classic Jacket in Six New Fabrics

I’m in Italy where Stone Island gave me a first look at their new “No Seasons” capsule collection, where they took a jacket from their archives and updated it in six different fabrics Available in limited quantities this October I’m going...

By Jake Woolf
Stone Island's 1982 Blue Chore Jacket: Hemp, Indigo, Enzyme‑Washing Mastery
SocialApr 20, 2026

Stone Island's 1982 Blue Chore Jacket: Hemp, Indigo, Enzyme‑Washing Mastery

Went to the stone island HQ in Italy and all I got was to see was a jacket that will haunt me forever—this blue chore jacket from 1982 It’s made from a cotton hemp that was printed with indigo dye and...

By Jake Woolf
Thermo‑Sensitive Green Stone Island Jacket Revealed at HQ
SocialApr 19, 2026

Thermo‑Sensitive Green Stone Island Jacket Revealed at HQ

Got this incredibly cool Stone Island jacket that a) is a beautiful green but b) is done up in a thermosensitive nylon that changes colors in warm temperatures Im in Italy and heading to their HQ tomorrow to see the...

By Jake Woolf
Reached 25K Subscribers, Thankful for Substack Freedom
SocialApr 19, 2026

Reached 25K Subscribers, Thankful for Substack Freedom

Just passed 25,000 subscribers for the newsletter. Honored and humbled to have this many people sign up to see my product recommendations. Substack is by far my favorite venue to create content in, as it’s allowed me to do...

By Jake Woolf
Confidence Peaks in Rick Owens Sneakers and Plaid Shirt
SocialApr 18, 2026

Confidence Peaks in Rick Owens Sneakers and Plaid Shirt

How dudes feel walking into a party wearing Rick Owens DRKSHDW sneakers with their slim raw selvedge and plaid button up shirt https://t.co/gCKtQJtfME

By Jake Woolf
Influencer Praise Sparks Surge in Gap Hoodie Sales
SocialApr 18, 2026

Influencer Praise Sparks Surge in Gap Hoodie Sales

3 days ago I posted about Gap’s extra heavyweight hoodie being the best sub 100 hoodie on the market. 2 days ago it is reported Gap’s stock is booming. Coincidence? Or the latest work of the most influential voice in...

By Jake Woolf
Greg Laboratory Merges Science and Style in New Collection
SocialApr 17, 2026

Greg Laboratory Merges Science and Style in New Collection

Making clothes can be an art form, but to some designers, it’s more of a science One such brand is NYC-based Greg Laboratory, so I visited their HQ to go BTS with its founder and see the new collection https://t.co/3EUjeMdKs9

By Jake Woolf
Loose Chinos, Boat Shoes, No Socks: Ultimate Sluttiest Look
SocialApr 15, 2026

Loose Chinos, Boat Shoes, No Socks: Ultimate Sluttiest Look

The sluttiest thing a man can wear is a loose fitting chino and boat shoes sans socks 😉 https://t.co/gdpoQOYp5i

By Jake Woolf
Printed Camp Collars: Still Summer‑Ready When Styled Retro
SocialApr 12, 2026

Printed Camp Collars: Still Summer‑Ready When Styled Retro

The printed camp collar shirt trend got out of control in the last half decade, but I think there’s still room for them in a summer wardrobe The trick is if you’re gonna wear it you gotta go full Don Draper...

By Jake Woolf
1940s Movado Chronograph, 14k Gold, $25,995
SocialApr 12, 2026

1940s Movado Chronograph, 14k Gold, $25,995

Insanely good 1940s Movado chronograph with applied breguet numerals 14k yellow gold, 33mm Francois Borgel case Asking price: $25,995 (Available for sale via goldfingersvintage) https://t.co/tZC1OByld4

By Jake Woolf
Ralph Lauren's Polo Sportsman Hat Leads Stellar Collection
SocialApr 11, 2026

Ralph Lauren's Polo Sportsman Hat Leads Stellar Collection

Ralph Lauren is currently on a generational run of excellent hats in the collection The polo sportsman in particular is a need https://t.co/CzGvdRaHMK

By Jake Woolf
Scored Vintage Armani Jacket for $45—Best Wardrobe Find
SocialApr 10, 2026

Scored Vintage Armani Jacket for $45—Best Wardrobe Find

My vintage Armani Le Collezioni double breasted jacket is probably the best single item of clothing I own and it was $45 on eBay in 2022 https://t.co/qa6i6my9eF

By Jake Woolf
Spring Switch: From Wool Coats to Oxford Shirts
SocialApr 10, 2026

Spring Switch: From Wool Coats to Oxford Shirts

Finally spring…farewell to the fits solely defined by a heavy wool overcoat, and hello to outfits defined by an oxford shirt, vintage Levi’s, and sweater over the shoulder https://t.co/v2SKRtSzoc

By Jake Woolf
Design Your Own Shoes, Wear Them Proudly
SocialApr 10, 2026

Design Your Own Shoes, Wear Them Proudly

Wearing nice shoes is cool—wearing nice shoes you helped design is cooler Jake Woolf x Blu Scarpa “La College” penny loafer made in Italy from your choice of spazzolato calfskin or genuine crocodile skin. Available now at the link in...

By Jake Woolf
Perfect Penny Loafer Launches Handmade in Italy
SocialApr 10, 2026

Perfect Penny Loafer Launches Handmade in Italy

For the last few months I’ve been quietly working on what I wanted to be a perfect penny loafer I did it alongside one of my favorite independent shoe brands, Blu Scarpa Today, that shoe is available for purchase. Calfskin or croc...

By Jake Woolf
Diving Deeper Into Vintage Polo: My New Challenge
SocialApr 9, 2026

Diving Deeper Into Vintage Polo: My New Challenge

I’ve had some nice vintage Ralph Lauren pieces throughout the years, but I am now officially throwing down the gauntlet in the vintage Polo arena https://t.co/UP00w9alQg

By Jake Woolf
First‑ever Shoe Design: Soft Burgundy Loafer Drops Tomorrow
SocialApr 9, 2026

First‑ever Shoe Design: Soft Burgundy Loafer Drops Tomorrow

For the first time ever I helped design a shoe, and it drops tomorrow We basically took a classic polished burgundy penny loafer and made it soft right out of the box. Handmade in Italy. $530 Available early access to...

By Jake Woolf
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