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Romantic Outfits to Wear on Valentine’s Day: A Gentleman’s Guide

Valentine’s Day dates are any­thing but “one size fits all.” Whether you’re going for a roman­tic din­ner with your long-term part­ner, try­ing to wow a new love at the sym­pho­ny, or get­ting ready to pop the ques­tion, a Valentine’s Day suit or tux should be on your V‑Day to-do list. With 21 unique valentine’s suits to choose from, and hun­dreds of acces­sories to help make it your own, Gen­er­a­tion Tux has all of the secret weapons for mak­ing you look your best on Feb­ru­ary 14th.

We’ve seen plen­ty of guys suit up for a spe­cial Valentine’s Day date over the years, and we’re here to share some of our favorites. Below are our top choic­es for Valentine’s Day attire for men.

You: A tech-wiz, a part­ner at a start-up, and a lover of craft beer.

The Date: A 12-course tast­ing menu at an exper­i­men­tal mol­e­c­u­lar-gas­tron­o­my bar. 

The Look: Your office tends to have a more casu­al vibe, but now’s the time to show your part­ner anoth­er side of your style. Rock­ing a Valentine’s Day suit is more than appro­pri­ate for a tast­ing-menu date. Try an indi­go suit with no tie, and a pat­terned shirt—we sug­gest ging­ham. When you’re wear­ing this suit, you will be just as eye-catch­ing as the per­fect­ly plat­ed dish­es you’ll be try­ing all night.

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You: A nat­ur­al come­di­an with a big smile and an even big­ger per­son­al­i­ty.

The Date: A night at the opera, fol­lowed by a fan­cy dessert in the city.

The Look: When you go to the opera or the­atre, a tuxe­do should be your new best friend…especially on Valentine’s Day. A light grey tux is a beau­ti­ful choice for the occasion—it’s not as fan­cy as a black one, but still gives an air of ele­gance and hon­ors the impor­tance of the evening. You can even plan ahead and match your bow tie or pock­et square to the col­ors your date is wear­ing.  

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You: A world trav­el­er, whiskey snob, and slight bib­lio­phile.

The Date: A French film, hors d’oeu­vres, and cham­pagne at an under­ground cin­e­ma and club.

The Look:  Ooh là là. Valentine’s Day is the per­fect excuse to go with an ultra-roman­tic look. A night of French cin­e­ma and bub­bles calls for a clas­sic black, red, and white com­bo. How about a black notch lapel suit with a ruby red lapel rose and pock­et square? You can play around with vest colors—grey or black both look excel­lent here. 

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You: A tat­tooed lover of all things food and drink.

The Date: Din­ing at the chef’s table at your buddy’s impos­si­ble-to-book restau­rant. 

The Look: Arrive at the restau­rant rock­ing a pair of dark jeans with a but­ton-down and vest. Throw on a pair of boots, roll back your jack­et and shirt sleeves to show off those tats, and you’re gold­en. 

You: A sports lover,  grill­mas­ter, and proud dog Dad.

The Date: A craft brew­ery tour, fol­lowed by a spe­cial beer pair­ing meal onsite. 

The Look: This is a great time to pull out your nicest sweater. Pair it with jeans, dress shoes, and a casu­al suit coat. You’ll look ele­gant with­out seem­ing over­dressed. 


You: A nature-lov­ing father of two.

The Date: A babysit­ter at home and a love­ly, local din­ner for two.

The Look: You’ve already sprung on the babysit­ter, why not go the extra mile and wear a spe­cial Valentine’s Day suit?  We know you’re prob­a­bly more tired these days, but believe us, it’s an easy and enjoy­able way to show the romance is far from dead. So, knock back an espres­so shot and slip into a gray shark­skin notch suit and brown loafers. Pink accents work real­ly nice­ly here—a rose pock­et square and tie will pull every­thing togeth­er.

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You: A music-lov­ing, cof­fee-fueled, hope­less roman­tic.

The Date: A walk along the riv­er with your gui­tar. A ser­e­nade, and a pro­pos­al.

The Look: While your every­day style may be a bit “record­ing stu­dio,” tonight you want to look more like you’re on an album cov­er. You can wear jeans, but make sure they’re in good con­di­tion. Pair them with a smart but­ton-down, boots, and a leather or suede jack­et.

You: A ded­i­cat­ed and hard work­er, both at the office and in dai­ly life.

The Date: A  candlelit—and elaborate—homemade din­ner.

The Look: Your part­ner has like­ly seen you suit up hun­dreds of times. Tonight, you’re stay­ing in, so it might be the occa­sion to try a dif­fer­ent, more casu­al roman­tic look. A tight-knit sweater paired with some hand­some slacks and loafers cre­ate a debonair “Don Drap­er on the week­end” kind of vibe…and we’re here for it.

You: A clas­sic South­ern “good old boy.”

The Date: A sun­set river­boat cruise with cham­pagne and din­ner.

The Look: A white tux with a shawl lapel is a dreamy option for a river­boat cruise. This suit is gen­teel and hap­pens to look fan­tas­tic next to a col­or­ful sun­set. Plus, white goes with any­thing, so you are sure to match what­ev­er your date choos­es to wear.

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What­ev­er you choose to do this Feb­ru­ary 14th, Gen­er­a­tion Tux is here for all your Valentine’s Day suit needs. Cus­tomize your own look online today and have it deliv­ered right to your door—Looking good has nev­er been this easy.

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