New York City, the epicenter of American fashion, and home to some of the best dressed gentlemen in the world. But why is it that we no longer see the preppy kind strolling down the crowded streets of Manhattan? Last time I checked, preppy was still in.

Brands like Ralph Lauren, Tommy Hilfiger, Nautica, and even designer Nick Graham embraced the ivy-league-inspired ensembles on the catwalk during the last New York Fashion Week: Men’s. Models like Sean O’Pry and River Viiperi can attest to that. Still don’t believe me? Just ask fashion icon and ambassador of the Council of Fashion Designers of America (CFDA) Johannes Huebl, who is the perfect example of this classic style himself.

With preppy stores scattered all over Manhattan, you’d think it’s easy to find the right pieces for an outfit. But if all fails, or if you can’t afford shopping, there’s always your imagination and your creativity to turn to as well, even if it involves unexpected brands. You don’t have to wear high end labels and drain your bank account to look good. You can still be elegant for a quarter of the price—or even without spending any money at all—so let’s just get creative. We all have a preppy gentleman within, we just have to learn how to dress him… And what better time of the year to do so than spring? Let’s bring back this classic American look, shall we? We’re on the East Coast, after all.

For this ensemble, I started with a blue dress shirt from H&M, and I put on a tie from Tommy Hilfiger with gold and royal blue diagnal stripes (gotta love that preppy tie pattern!). Growing up, I was told several times not to mix check patterns with diagnal stripes, because apparently it looked “funny,” but as I grew up and evolved, so did fashion. So this time around I matched them both, and then I neutralized them with a grey sweater vest, also from Tommy Hilfiger. I almost wore said vest but in navy blue (pictured below), until I noticed how monocromatic the ensemble looked when I put on my wool plaid blazer from Ralph Lauren’s Lauren collection. Don’t get me wrong, a monocromatic outfit can still look good, and it keeps things uniform; which is totally fine and can actually work, if you’re into that. But for this outfit, I wanted to play with the colors of the spring and keep adding to the contrast.

By the way, isn’t that blazer to die for? As you may have noticed, it is the most high end piece complementing the combo, and it’s certainly the main one that really gives it an elegant vibe. I still wanted to keep it all affordable and down to earth, though, so I chose to wear pink jeans from H&M, which I rolled up at the bottom to keep the look fun and fresh; and also to give this classic American style a modern semi-casual twist, which is why I thought my Sahara Sperry top-siders would be the perfect accesory. Then I balanced out the bottom part of the look by wearing my cogniac belt from H&M. Oh and just in case you’re wondering, I’m not afraid, nor am I ashamed to wear pink. If you ever feel daring enough to sport pants like these, do it with confidence.

In this concrete jungle, where everyone seems to embrace streetwear, casual looks, or Wall Street business attire, a well-matched and carefully thought out preppy ensemble like this one will definitely stand out. It will make you feel confident, elegant, young and fresh, but with a slight touch of nostalgia. Granted you should always dress up for yourself, and you shouldn’t strive to be the center of attention, but just in case you were looking to boost up your self-esteem and wondering what kind of feedback you’ll be getting, I guarantee you’ll be showered with compliments and smiles within seconds, I’m talking first hand here.

Speaking of feedback, let me know what you think in the comments section below.

Elegantly yours,


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