Dappered Classics: How to Roll Up Your Sleeves

How To Roll Up Your Sleeves – The Italian Way.

Originally published 6/16/2010

For as great as our President can look when he’s dressed to the nines, the guy sure does struggle when it comes to loosening the collar and relaxing a bit.  The man still tucks his t-shirt into his sweatpants when he plays basketball.  Anyway…

See the President’s roll up there?  Don’t do that.  The guy looks like he has a cotton bagel halfway down his forearm.  Here’s what you want to do:

  • Unbutton the cuff.
  • Grab the edge of the cuff and flip the whole cuff back.
  • Allowing your sleeve to turn inside out along the way, drag the cuff slowly up past your elbow until the now bottom seam of the cuff is in your elbow pit.
  • Fold the extra 3-5 inches of exposed inside-out sleeve up to “lock in” the cuff.
  • Done.

You’ve got a cuff right above your elbow that’s not going anywhere.  It’s amazing how well this looks and works.

Need a new dress shirt to do this with?  Try the Alfani Red Tonal Stripe, or the DKNY Fitted Stripe.

Step 1: Flip. Step 2: Drag. Step 3: Flip and lock in.

Joe

Recent Posts

Huckberry: 15% off Sitewide Annual Sale

72-hour merino shirts. 365 pants. Blazers and chore coats. Hamilton watches, Italian made boots, and…

9 hours ago

The Best Men’s Style Sales for Singles’ Day / Veterans Day

Spier topcoats, Grant Stone tiers, and Bonobos does a surprise inclusion of their icon Weekday…

2 days ago

Skimp, Spend, Splurge: 10 Types of Fall & Winter Coats & Jackets

Exploring 10 styles of men's outerwear, each with specific options at three different price tiers.

3 days ago

Bonobos 30% off most Pre-Holidays Sale

Now extended through Thursday. It's their "Treat Yourself" event. Select flagship chinos. Stretch premium jeans.…

3 days ago

Steal Alert: 40% off most everything at Brooks Brothers

48 hours only. No bulk buy or rewards club requirements. Just a flat, 40% off.…

3 days ago

Most Wanted Affordable Style – November 2026

Roaring 20s styled watches, restocked half-canvas suits under $300, & more.

4 days ago