Jake Woolf

Jake Woolf

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

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