Jake Woolf

Jake Woolf

Creator
0 followers

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

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