I don’t mean to freak you out, but Valentine’s Day is fast approaching. You already know your plans for the evening. Right? (You’re welcome). An impressive date is only part of the equation, though. You know she’s going to look hot, but what about yourself? Yes, you. It’s the most romantic evening of the year, ergo . . . you should definitely dress to impress regardless of your relationship status. I know that the idea of dressing up might seem overwhelming for the guy whose daily uniform includes jeans and a shirt that doesn’t smell. But that’s why I’ve enlisted Leo Petaccia, Founder and Lead Stylist of Toronto’s Two Dudes Shopping Co., to help you out. We’ve got you covered on all fashion fronts, from the ultimate formal dinner to the going-out-but-still-casual to the staying-at-home. The only thing we haven’t done for you is help pick out a gift for your Valentine. Oh, wait.
Super-Duper Fancy Romantic Date
So you’re pulling out all the stops this Valentine’s Day. A fancy, schmancy joint that probably requires two sets of forks and spoons, and most definitely a suit. Well, don’t fret because we’re not going to suggest you dress like a penguin.
“More and more men are embracing fashion and returning to the days of yore, when gentlemen in ties, pocket squares, blazers and brogues were a common sight,” Petaccia says. “Now we’re seeing this sort of thing again, and actually, we’re going to take those pieces to make our fancy outfit, which won’t be “Look-At-Me-I’m-In-A-Tux-With-No-Oscars-To-Go-To,” but more like, smart, modern professor.”
And ladies really dig the smart, sexy look, FYI.
According to Petaccia:
- Start with a handsome tweed blazer that’s both a) made in a bold, yet classic print (think micro herringbone, or a glen plaid if you wanna look like a fucking boss, like this one) and b) modernly cut so that it’s fitted to its wearer’s frame. You can find a great one at Brooks Brothers. So, narrow lapels, preferably notched, and the jacket should be slightly shorter at the bottom so your ass isn’t covered. That’s ugly.
- Next, go with a nice, simple oxford shirt that’s more elegant than collegiate (i.e. this one from United Stock Dry Goods in Toronto). The shirt should fit well, too. No billowing at the bottom or in the arms.
- Then, add a solid knit tie that’ll match anything, like this red lambswool one from a shop in Parkdale called elevator (’cause fuck it, it’s Valentine’s Day, so wear some red). It’s also got an interesting texture, plus it’s reversible, offering a deep burgundy that’s perfect for the fancy date outfit. And it’s a non-cliché play on wearing red for Valentine’s Day.
- Add a pocket square that matches the tie/shirt combo, bringing out a colour in either or both (this is what you always do when matching shirt-tie-pocket square). But really, a white, silk pocket square neatly folded and tucked in well enough so it’s peeking out is perfect here. It’s old school, but perfect.
- Next are the trousers. Something simple, fail-proof, and absolutely handsome, like this pair of grey, tailored, twill wool trousers from Toronto’s 18 Waits.
- As for shoes, go with a pair of black brogues by Lost & Found x Tricker’s.
- Lastly, the socks! This is where you want to take advantage of patterns again. No one would ever suspect an animal print, so fucking do it up in a pair of these from HS Sweden.
- Bonus tip: If you add a tie clip, that’s a detail she’ll notice and really appreciate. Go with something understated, like this.
Casual Fun Night Out
This is for the type of date that’s not super fancy, but you’re still out in public with a cool woman on your arm, so you still want to look date-able . . . erm, presentable. As Petaccia says, “Even though casual’s the name of the game, there’s no excuse to look like slob. Let’s do something that’s easy, but smart, too. Also, it’ll likely be freezing, so layer like a motherfucker.” Plus, the more layers, the more fun it will be taking off later that night.
For your casual (but stylish) night out, Petaccia suggests:
- The basis of your outfit will be a dark, rugged henley shirt, like this one from Rag & Bone. (Conversely, a light one works perfectly, too).
- Contrast this with a playful, but relaxed, print or plaid shirt. Preferably this one from Uncle Otis.
- Then go back to basics with this jacket from Muttonhead. It’s utilitarian and can work in so many ways. Not to mention it’s stylish as fuck.
- As pants, try green (or maroon/burgundy) cargo pants. These. Never. Fail. But don’t cheap out. Get a good pair. Just make sure they’re fitted. And you know what? Roll ‘em up once or twice at the bottom. Looks modern.
- Get out of your comfort zone and wear some masculine jewellery. But nothing dumb or blingy. Something like this necklace (erm, “man chain”?) would be a perfect detail to add.
- Finish things off with a fresh pair of sneakers. Grab a pair of all white, high cut ones, like these from Easy Tiger.
- Cap off the outfit with a . . . cap. Dudes love hats, too, and again, it’ll be freezing, so you’ll want your head to stay warm and stylish. I love these from local brand KIN available at Sydney’s in Toronto.
Cozy Night At Home
So you and your Valentine opted for a cosy night in with Netflix, takeout and a nice bottle of wine. Sounds great. But don’t think for a minute you can wear your shitty clothes just because you’re sticking close to the sofa. “Now that sportswear and sweats are being taken seriously by designers, more and more folks have embraced the super laid back look,” says Petaccia. “Which is great, since you once again have an excuse to wear joggers whilst entertaining your lady. But again, they’ll be stylish, fitted joggers. No cutting fucking corners.”
- To stay comfortably cool, Petaccia recommends:
- Sweats, but fashionable ones, like these ones from B.C. brand, Reigning Champ. Canadian, and cosy. It’s a win-win.
- Nothing says “Snuggle me and make out with me” like a warm, slightly oversized fisherman sweater. The more intricate the knitted designs, the better. I’d go with this one from Philistine on Queen West in Toronto.
- Oh yeah, put a white t-shirt on underneath this. No excuses.
Now, go get her, you sartorial sonofabitch!
Brianne Hogan is a freelance writer based in Toronto, something of a humorist, and considers herself more Bridget Jones than Samantha Jones. Though she won’t reveal which parts, she will admit to liking emotionally unavailable men and drinking lots of wine. You can follow her on Twitter @briannehogan.