We understand why guys feel stressed about Valentine’s Day. They’re expected to find the perfect gift, plan a romantic night and look devilishly handsome—like, Ryan Gosling devilishly handsome—all the while. To help with the latter, we put together three easy-to-assemble Valentine’s Day outfits that range from breezy-night-at-the-bar attire (hint: don’t go to a pub, especially one with a name that ends in Firkin) to the right duds for a fancy evening of fine-dining, whispered words and maybe even more.
Low-Key What to wear for drinks and bar snacks at a casual downtown joint.
Finally, opt for boots over sneakers. <strong>Cole Haan’</strong>s chukkas have a classic fit with an unexpected pop of colour around the sole. $255.<br />
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<em>Available at Cole Haan, 101 Bloor St. W., <a href="http://www.colehaan.com/colehaan/catalog/product.jsp?catId=100&productId=726765&productGroup=726714">colehaan.com</a></em>
You can get away with jeans on Valentine’s Day, as long as they’re slim and have a dark wash like these, by Toronto’s <strong>United Stock Dry Goods.</strong> $135.<br />
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<em>Available at Sydney’s, 682 Queen St. W.,<a href="http://shopsydneys.com/denim/united-stock-dry-goods-12-5-oz-narrow-indigo-contrast-stitch-denim.html">shopsydneys.com</a></em>
A cozy shawl-neck cardigan from <strong>Club Monaco</strong> is smarter than a sweatshirt and cozier than a jacket. $149.<br />
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<em>Available at Club Monaco, multiple locastions, <a href="http://www.clubmonaco.ca/product/index.jsp?productId=17207786&cp=12266410.12280856.12770913&ab=ln_men_apparel_sweaters">clubmonaco.ca</a></em>
A casual look starts with your favourite plaid shirt. We like this one from <strong>Band of Outsiders</strong> for its slim fit and muted colours. $99 on sale from $305.<br />
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<em>Available at Jonathan and Olivia, 49 Ossington Ave., <a href="http://jonathanandolivia.com/HIGHLAND-PLAID-SHIRT-BROW.html">jonathanandolivia.com</a></em><br />
<strong>Grenson’</strong>s leather wingtips fit the conservative tone of this outfit—the company has been making them since 1866, after all. $345.<br />
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<em>Available through <a href="http://www.gravitypope.com/shoes/product/21990-grenson-5139-01-dylan#also-like">gravitypope.com</a></em>
On a normal date night, you could get away with khakis or jeans. On Valentine’s Day, however, we recommend upgrading to narrow-leg suit trousers by <strong>A.P.C.</strong> $88.50, on sale from $295.<br />
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<em>Available at Nomad, 819 Queen St.W., <a href="http://store.nomadshop.net/collections/bottoms/products/apc-pntant">nomadshop.net</a></em>
Rather than a ho-hum white shirt, try a gingham dress shirt from <strong>Brooks Brothers.</strong> $88.<br />
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<em>Available at Brooks Brothers, 200 Bay St., <a href="http://www.brooksbrothers.com/Supima%C2%AE-Cotton-Non-Iron-Extra-Slim-Fit-Gingham-Dress-Shirt/ME01167,default,pd.html?dwvar_ME01167_Color=BLUE&contentpos=3&cgid=0203">brooksbrothers.com</a></em>
A classic date look begins with a navy blazer. This <strong>Boss Black</strong> jacket has contrast stitching on the lapel and pocket flaps for a little extra visual interest. $498.<br />
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<em>Available at Harry Rosen, multiple locations, <a href="http://www.harryrosen.com/eng/products/outerwear/jackets/navy_cotton_neat_blazer?05080991">harryrosen.com</a></em>
Finish the look with <strong>H by Hudson</strong> cap-toe lace-ups. And make sure they’re shined. $290.<br />
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<em>Available through <a href="http://www.gravitypope.com/shoes/product/18551-h-by-hudson-4619240-tan-habana">gravitypope.com</a></em>
If you’re really into the Valentine’s Day spirit, go for red neckwear—if not, a blue tie from <strong>Club Monaco</strong> also works. $98.50.<br />
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<em> Available through <a href="http://www.clubmonaco.ca/product/index.jsp?productId=18359206&cp=12266410.12280881.12774160&ab=ln_men_shoesaccessories_tiespocketsquares">clubmonaco.com</a></em>
Pick a shirt in pink or red as a nod to the occasion. This one by <strong>Kin </strong>has a red grid pattern that looks pink from farther away. $149 on sale from $285.<br />
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<em>Available through <a href="http://shopsydneys.com/tops/kin-long-sleeve-structured-collar-double-grid-shirt.html">shopsydneys.com</a></em>
Nothing impresses like a well-fitting suit. This one from <strong>J.Crew’</strong>s Ludlow collection is made of luxurious Italian wool and has a trim silhouette. Jacket, $512; pants, $225.<br />
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<em>Available at J.Crew, Eaton Centre and Yorkdale Shopping Centre, <a href="http://www.jcrew.com/mens_feature/TheLudlowShop.jsp">jcrew.com</a></em>