Jake Woolf

Jake Woolf

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

Vintage Ralph Lauren Linen Shirt Leads Summer Wardrobe
SocialMay 11, 2026

Vintage Ralph Lauren Linen Shirt Leads Summer Wardrobe

A new vintage Ralph Lauren “big shirt” has entered the villa, this time in linen This and my rotation of blue oxfords will be the starting lineup of this summer https://t.co/HsmqPiVMJJ

By Jake Woolf
Japanese Asahi Costs Twice Sperry, Which Wins?
SocialMay 10, 2026

Japanese Asahi Costs Twice Sperry, Which Wins?

Preparing to do a deep dive comparison on the Asahi deck shoe vs their OG, the Sperry CVO But based on these two shots alone, which do you like more? Asahi is $185 made in Japan, Sperry is $90 and...

By Jake Woolf
LES Flooded with Calf‑length Jean Shorts
SocialMay 10, 2026

LES Flooded with Calf‑length Jean Shorts

Me after walking around the LES and seeing all the dudes in calf-length jean shorts

By Jake Woolf
Real McCoys Nail Vintage Navy Gold Button Blazer
SocialMay 10, 2026

Real McCoys Nail Vintage Navy Gold Button Blazer

The Real McCoys makes near perfect recreations of vintage military gear, and they’ve done it again with this US Navy gold button blazer This with a white polo, some big chinos and LHS loafers? Cmon now https://t.co/8lZ6aTs60C

By Jake Woolf
NY Tailor Reveals Summer Wedding Suit Essentials
SocialMay 9, 2026

NY Tailor Reveals Summer Wedding Suit Essentials

Summer wedding suit season is here, so I went to my favorite tailor in NY to find out what I’ll be wearing to all my summer weddings on the calendar. If you’re wondering what to wear then watch for inspo—from...

By Jake Woolf
Paraboot Barth Beats Sperry at $300
SocialMay 9, 2026

Paraboot Barth Beats Sperry at $300

Respect to the OGs at Sperry but at $300 the Paraboot Barth absolutely mogs A real ball knower boat shoe https://t.co/bA6VtIsaZr

By Jake Woolf
Internet Bans Socks with Fisherman Sandals—63 Days Straight
SocialMay 7, 2026

Internet Bans Socks with Fisherman Sandals—63 Days Straight

When the internet says for the 63rd day in a row to not wear socks with fisherman sandals

By Jake Woolf
Copy Paul Newman's Style, Look Better than Most
SocialMay 7, 2026

Copy Paul Newman's Style, Look Better than Most

The thing about Paul Newman’s style is that while attainable, you will never look as innately cool as Paul Newman because he was Paul Newman and you are not However, this is okay, because chances are you will still look better...

By Jake Woolf
Pick One Luxury Shoe Pair for Your Trip
SocialMay 7, 2026

Pick One Luxury Shoe Pair for Your Trip

You’re going on a trip and can only take 1 pair. Choose your fighter 1. Crockett & Jones Harvard 2. John Lobb Lopez 3. Alden Leisure Hand Sewn 4. JM Weston 180 https://t.co/wfXpGqr6Vx

By Jake Woolf
Baby Blue Socks Pair Perfectly with Shell Cordovan Shoes
SocialMay 7, 2026

Baby Blue Socks Pair Perfectly with Shell Cordovan Shoes

Baby blue socks and shell cordovan color 8 shoes: a springtime color combo match made in heaven https://t.co/zEPJEOB3vc

By Jake Woolf
Discover Milan’s Premier Classic Menswear Destination
SocialMay 6, 2026

Discover Milan’s Premier Classic Menswear Destination

On a recent trip to Milan, I stopped by the store of one of the best brands in the world for fans of all things classic menswear—from Oxford shirts and boat neck sweaters to Japanese made denim, tuxedos, loafers, and...

By Jake Woolf
Chinos Should Be Relaxed: 16 Top Picks
SocialMay 6, 2026

Chinos Should Be Relaxed: 16 Top Picks

In a world dominated by slim stretch chino slop, I’m here to tell you that this is actually how they should fit. Chinos are chill, and deserve to look like it. That plus my 16 favorite chinos to buy right...

By Jake Woolf
Classic American Summer: Chinos, White Socks, Cordovan Shoes
SocialMay 5, 2026

Classic American Summer: Chinos, White Socks, Cordovan Shoes

Ralph Lauren chinos, white socks, shell cordovan Aldens A time-tested American summer tradition unlike any other https://t.co/V0zZa89flL

By Jake Woolf
RRL vs Polo Country: Which Chore Coat Wins?
SocialMay 4, 2026

RRL vs Polo Country: Which Chore Coat Wins?

Ralph Lauren is currently making two excellent chore coats Left is RRL: slightly slimmer fit, more “distressed” wash, corduroy collar Right is Polo Country: loose fit, even medium wash throughout Which do you like better? https://t.co/eshfFGzBnH

By Jake Woolf