A Valentine's Day Style Guide: Where To Go And What To Wear

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February 14th is right around the corner, and that means many dudes are scrambling to think of the perfect way to impress their boos. Jewelry is always a safe bet, and chocolate might do the trick too, but sometimes it helps to go the extra mile, especially when it comes to what happens later that night.

Whether you're just starting out with a new jump-off or practically married to your girl, thinking of where to take that special someone is hard enough, let alone putting together a good outfit. Here to take the guesswork out of how to show her a good time and look good while doing it, here's A Valentine's Day Style Guide: Where To Go And What To Wear.

Basketball Game Night

Where: Toronto Raptors vs. New York Knicks, tickets here 

Jeremy Lin Road T-Shirt
Buy It Now at New York Knicks Store, $25 

Girls "Linsanity" T-Shirt
Buy It Now at New York Knicks Store, $28

Canada Goose Ontario Parka
Buy It Now at Backcountry.com, $590 

Jordan Melo M8 Sneakers
Buy  It Now at Foot Locker, $120 

Salute! You've scored a girl who loves b-ball. Take her to Toronto in time to see current Knicks star, Jeremy Lin, in action against the Toronto Raptors. Alternately, a nice sports bar could work too. Just be sure to rep the team in these great graphic tees. Of course, finish up the ensemble in some Melo kicks. If you do choose to head up north, you might need a warm parka, and this Canada Goose jacket is appropriate in more ways than one.

Dinner at Home

Where: Your place.

Finisterre Coho Plain Sweatshirt
Buy It Now at Finisterre, $79

Pixel Heart Socks
Buy It Now at Topman, $6 

DURKL Fanatic Denim
Buy It Now at DURKL, $93 

Birkenstock Amsterdam in Petrol Wool
Buy It Now at Birkenstock, $100 

Govino Shatterproof Wine Glasses
Buy It Now at MOMA Store, $14 

Chateau Marsac Seguineau 2009
Buy It Now at Wine.com, $25

Stone Candleholders
Buy It Now at Design Within Reach, $28-$40 

Whether you live with your significant other or are just inviting her over, women love a man that can cook. Making a meal means looking presentable but also comfortable, so a crewneck sweatshirt and pair of washed jeans fits the bill. If you wanna add a little more class, throw on a blue oxford buttondown shirt under the sweatshirt. There's no need for a tie in this setting. For footwear, you don't need to lace up your best wingtips, but you don't want to rock flip-flops either. These Birkenstocks are a good balance between comfort and style, and you can wear them out to the grocery store if you need to pick up some ingredients. 

Set the mood with some candles, a good Bordeaux wine, and these stylish wine glasses, and good luck.

Night Out

Where: Angel's Share, New York City

Penguin Houndstooth Wool Blazer
Buy It Now at Park & Bond, $225 

Jil Sander Quilted Overcoat
Buy It Now at Barneys, $639 

Ovadia & Sons Pistachio Flannel Trousers
Buy It Now at Ovadia & Sons, $198 

Cole Haan Air Monroe Loafers
Buy It Now at Cole Haan, $198 

Stussy Deluxe Ettinger Wallet
Buy It Now at Stussy, $350

A night out on the town is great for new couples and old couples, you can both discover new places or revisit old haunts from when you first started dating. It's best to hit up places that can facilitate conversation, like the classy Angel's Share bar in the East Village, a cocktail lounge hidden behind a Japanese restaurant. As long as it's just the two of you, getting seated shouldn't be a big deal. Keep things elegant with a subtly patterned blazer and warm flannel trousers. Should you decide to barhop, a good overcoat is key, as well as shoes you can walk in. Thankfully these Cole Haan loafers have a Nike Air sole. Also, if you've still got the same wallet from college, it's time to upgrade. Since you'll be paying for the tab, chances are she'll be seeing what you keep your cash in, so make sure it looks as good as you do.

Hotel

Where: The Standard

Bedford Navy Wax Overnight Bag
Buy It Now at Ernest Alexander, $465 

Norse Projects Hak Suede Jacket
Buy It Now at Norse Projects, $950

Levi's 511 Corduroys
Buy It Now at Footaction, $30 

ATM V-Neck T-Shirt
Buy It Now at Barneys, $72 

Billy Boy Condom Tin Pack
Buy It Now at Billy Boy, $8 

An overnight stay at a hotel is fun because it's kind of dirty in the sense that you both know what's gonna go down at the end of the night, and the setting is unfamiliar to both of you. Pack light but invest in a heavy jacket, suede bombers are what the cool kids are all about these days. Bring basics like super soft T-shirts and comfortable pants that can stand the weather like corduroys. Lounge by the jacuzzi and get white girl wasted with your lady, and at the end of the night, don't forget to wrap it up.

Theater

Where: War Horse at the Vivian Beaumont Theater, tickets here 

J. Crew Ludlow Wool Suit Jacket 
Buy It Now at Mr. Porter, $455 

J. Crew Ludlow Wool Suit Trousers
Buy It Now at Mr. Porter, $195

Gitman Vintage Red Chambray Shirt
Buy It Now at Gitman Vintage, $165 

Gitman Vintage Portree Tartan Tie
Buy It Now at Gitman Vintage, $75 

Florsheim Veblen Wingtips
Buy It Now at Florsheim, $170

Stanley 8 oz Flask
Buy It Now at Manventure Outpost, $15 

Boys take girls to the movies. Men take their women to the theater. Get yourself some culture and take your lady to a show. Besides, if you've seen that episode of South Park, you know what's up with Broadway anyway. You'll want to look sharp in a versatile charcoal suit. Channel the special day with a red chambray shirt and patterned tie, and finish off your outfit with a pair of solid wingtips.

The show War Horse will keep you both enthralled and has an ending that won't leave either of you feeling sad afterwards. If you really can't stand theater though, know that most of them do serve alcohol, but just in case, you might want to bring a flask.

Buggy Ride

Where: Manhattan Carriage of NYC, book here

Orignal Gloverall Duffle
Buy It Now at Gloverall, $465 

Woolrich Hudson Bay Blanket
Buy It Now at Cabela's, $240-$400 

S.N.S. Herning Stark Cardigan
Buy It Now at End Clothing,  $259

Treat your girl like Cinderella by taking her on a good old-fashioned carriage ride before dinner. Dress warmly with a thick toggle coat and substantial cardigan, and bring a blanket along in case she needs a little bit of extra protection. As far as etiquette is concerned, cuddle in the coach... and then make out in the cab home later.

Rock Concert

Where: The Cake Shop, event schedule here

DRKSHDW Denim Pants
Buy It Now at The Corner, $390 

GHSTS Obliteration T-Shirt
Buy It Now at Always Never, $55 

Outlier Pivotal Bomber Jacket
Buy It Now at Outlier, $290 

Doc Martens 1461
Buy It Now at Doc Martens,  $110

Convince your hipster girlfriend to leave Bushwick and hang out in Manhattan for a change. Sure, The Knitting Factory has some good shows now and then, but the Lower East Side still has some cool spots worth checking out, like Cake Shop, where cheap shows and cheap drinks go hand-in-hand. Dress for the occasion by channeling Jordan Catalano and Trent from Daria with dark jeans, a washed-out graphic tee, Doc Martens, and a black bomber jacket. Rock on all night. 

Ice Skating

Where: Rockefeller Center, info here

Schott G-1 Cowhide Leather Bomber Flight Jacket
Buy It Now at Schott NYC, $1,125

Outlier Woolback OG Chinos
Buy It Now at Outlier,  $220

Wallace & Barnes Everett Check Flannel Shirt
Buy It Now at J. Crew,  $98

Carharrt Watch Cap
Buy It Now at Arvada Surplus,  $9

A classic date that can't go wrong and gives her an excuse to hold your hand for an extended amount of time. Add in some hot cocoa and ample amounts of whiskey and Irish cream, and you've got a fun, affordable date on your hands. Keep warm with a lined leather jacket and pants made for the weather. These Outlier chinos are lined in comfortable merino wool. Add an extra layer with a thick flannel shirt, and protect your head with a beanie.

Day At The Spa

Where: SpaCastle, info here

James Perse Jersey T-shirt
Buy It Now at Mr. Porter, $45 

U.S. Alteration Zip Hooded Sweater
Buy It Now at Union, $140 

Publish Jogger Pants
Buy It Now at Publish, $76 

Vans Italian Leather Slip-Ons
Buy It Now at Vans, $65 

If you haven't been to a Korean spa yet, you're living your life wrong. Take a personal day with your lady and TREAT YO' SELVES. You'll spend most of the day in very little clothing, so dress comfortably, since you'll probably be taking breaks to do things like grab a bite to eat. Opt for a comfortable T-shirt, a zip hoodie, these Publish Jogger pants that are like your favorite sweatpants mashed-up with your favorite chinos, and these leather slip-ons from Vans. They're simple but luxurious, kind of like a day at the spa.

Breakfast in Bed

Where: In bed, duh.

Engineered Garments Robe
Buy It Now at Park & Bond, $448 

Classic Pajama Pants
Buy It Now at J. Crew, $40

Mo's Bacon Chocolate Chip Pancake Mix
Buy It Now at Vosges Chocolate,  $12

Benito Breakfast In Bed Tray Table
Buy It Now at Fast Furnishings, $39

Preserved Rose Petals
Buy It Now at Things Festive, $16

Ok, this technically isn't a date, but the important part is, you already got her in the same bed. Whether you catch her by surprise on Valentine's Day or the morning after, you can't go wrong with breakfast in bed. Throw on a classy robe and a pair of pajama pants and mix up something savory and sweet like this mix for bacon chocolate chip pancakes. Throw it on a tray table with some preserved rose petals to set the mood. Just don't do the whole "rose petals on the bed thing" not only is that kind of corny, it's a real bitch to clean up.