On second thought, maybe cocky ascot is a little repetitive, because it’s pretty difficult to wear one without looking a bit arrogant. But sometimes, you want to look a little cocky, so this is the look for you.
Yes, there is a time and a place for looking a bit…cocky. Be careful with this one as you could easily be misconstrued as a blowhard rather than someone oozing with classic style. The look is obviously centered around the ascot, and our personal favorite is the simple navy polka dot piece by J. Press. Around it we have a brilliant french cuff shirt by Lugo that will create a perfect back drop for the piece. Throw on Reiss’ gorgeous peak lapel sport coat which looks more French Riviera than College Professor. Patrik Ervell’s winter jeans go perfectly with the look as they are so elegant with just a touch of sportiness. Keep it simple with your go-to penny loafers, the new Bass Dovers and you’ll have the look down pat. Avoid cufflinks on this one and opt for knots as they’ll keep you a little more casual. The real secret is being able to have the clout to pull it off, we’ll leave that one up to you.
Reiss Peak Lapel Corduroy Sport Coat, $335 at Reiss
J. Press Polka Dot Ascot, $89 at J. Press
Lugo Spread Collar Shirt, $195 at Lugo
Patrik Ervell Winter Jeans, $297 at South Willard
Bass Dover Loafers, $125 at Zappos