Dress To Impress This Valentine's Day 3 Ways | Men's Style Pro | Men's Style Blog & Shop

Dress To Impress This Valentine’s Day 3 Ways

With Valentine’s Day just around the corner, it’s time to get your look together. As we know, first impressions mean a lot in the dating game and leading online dating site EliteSingles is here to help. With the recent release of their #ItsADate Digital Bootcamp, that gives you five-steps to helping improve your first impression on a first date, EliteSingles reached out to Men’s Style Pro to create a few Valentine’s Day menswear looks. 

Ironically, the first point in the digital boot camp is – Dress To Impress.


Formal Valentine’s Day


EliteSingles x Men's Style Pro Valentine's Day Style Formal Look

Black Suit – Suitsupply | black & white checked pocket square – An Ivy Copenhagen | Double Monk Strap Shoes – Cobble & Hyde |Black Open Weave Knit Tie – The Tie Bar |Canfield 43mm Watch (Gold Case) – Shinola | Cutaway Collar White Shirt – Trashness

Every once in a while, donning your best suit on Valentine’s Day is the best way to go — so,  that means you might want go with a fancier themed date than usual. Based on a survey from EliteSingles, “83% of American believe wearing your best outfit, leaves a positive first impression”. If you’re getting this tailored, we assume this isn’t your first date, but, its worth it to continue to look your best. 

It’s rare that you’ll need to rock a tuxedo on Valentine’s Day (bravo to you if you do), but, you may to dress more formal. A black suit will give you just the right amount of formal and when styled right, you won’t look like you’re at the office. Be it an upscale dinner or a Broadway show, you can tweak a black suit to fit any occasion. Here’s a few steps to why this outfit works.

  • Physical Definitiona black suit is slimming (when tailored) and accentuates your shape at the same time. Showing off your physique without showing much skin is an art and entice (but,leave those deep v-necks alone)
  • Non-business Features: the checked pattern pocket square, cutaway collar shirt & knit tie says to your date “I might be suited up, but, I’m not stiff”.
  • Stepping Out : leave your Oxford lace-ups for the office and slip into their fashion-forward cousin the Double Monk Strap. They’ll leave just enough of an impression and show off your attention details. Good shoes are appreciated by everyone, so give yourself a leg up.

Luxe Casual


EliteSingles x Men's Style Pro Valentine's Day Upscale Casual Men's Style

70’s Vintage Suede Trucker Jacket – Levi’s| Giancarlo Castagno Brown Leather Chelsea Boots – Scarosso | Red turtleneck sweaterLa Fileria |Selvedge Denim Jeans Indigo Rinse – Uniqlo |Brown Croco Leather Band Watch – Kapten & Son | Demsey Sunglasses – Warby Parker | Auster arrowhead belt – J.Crew

When your Valentine’s plans are much more casual than the first scenario, there’s still a need to be well-tailored. Think of this look as the best version of your weekend style. Attending a comedy show, casual dinner or brunch (day dates are amazing)? This is look bridges casual and semi formal style. Mixing everyday pieces like selvedge denim with tailored menswear pieces like Chelsea boots & a fine-gauge turtleneck sweater, you luxe casual style will show off your everyday ability to look good. 

Feeling good and looking good is to key to any outfit. When you’re uncomfortable in your best outfit, it shows and the date can suffer. Just don’t forget about tailoring — let’s not be a Valentine’s Day slob.


At Home Sporty Casual


EliteSingles x Men's Style Pro Valentine's Day Casual Men's StyleSlim Indigo Navy Joggers – Todd Snyder| Cargidan Check Sweater – J.Crew | Watch – Timex | Sneakers – Nike | Denim Button Down Shirt – H&M

The cozy home date is a Valentine’s Day dream. Leaving the house is not required but you should still look like you give a damn. Being cozy doesn’t mean rocking  your PJs (unless that was the agreed upon attire), but, the right mix of athleisure and traditional tailoring will keep you relax & stylish. Below are a few tips pull off this look at home on V-day. 

  • Add One Standout Menswear Piece: a bold check cardigan is the epitome of comfy and traditional tailoring. It’s standout for its style and creates an illusion of formality when pair with the textured denim shirt. Think of this cardigan as the blazer 2.0
  • Minimal Sporty Kick: you may be wearing a pair of joggers, but, it’s not the time for your overly technical sneakers. A pair of white or navy minimal sneakers anchor your look just like a pair of Oxfords
  • Relax Your Watch: it’s always good to wear a watch on a date because it’ll keep you on time. Give your watch a relaxed makeover by switch to a nylon Nato strap in exchange for your metal band. They’re sport, tailored and can give your watch some personality

This feature was sponsored by EliteSingles (w/ stats provide Elite Singles). All styling & opinions are that of Men’s Style Pro.

Sabir M Peele

Founder & Creative Director

Founder & Creative Director of Men's Style Pro, Sabir has a deep passion for menswear and all things manly. Selected as one of the "5 Best Dressed Men In America" by Esquire Magazine in 2010 & as #GQFall 2013 Best Dressed Man. As of 2014, Sabir serves as a freelance brand ambassador & executive stylist for GQ Magazine & GQ Report. Outside of that partnership, Sabir serves as an independent brand consultant as well. Reach me directly at SABIR@MENSSTYLEPRO.COM

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