Dappered

Affordable Men's Style

  • Don’t Miss Anything
  • Start Here
  • Essentials Shop
  • Latest Deals
  • Style Scenarios
  • Reviews

What to Wear on Valentine’s Day. For Guys.

February 11, 2010 By Joe | Heads up: Buying via our links results in us getting a commission (not always, but just about), which helps keep the lights on around here. We also take your privacy rights seriously. Head here to learn more.

What to Wear on Valentine’s Day

Need Gift Ideas too? See our gift suggestions for starters.  From cheap to pricey, with both items and experiences up for consideration (since a lot of women would rather go DO something, than have another… something)

The so-called most romantic day of the year is coming up soon.  You’ve got a date.  Fantastic.  This is not the day to blow it in the style department.   Here are three suggestions on what to wear depending on where you’ll be and what you’ll be doing.

* * *

Destination: Staying in

Just because you’re spending a quiet night in on Valentine’s day doesn’t mean you can open up that bottle of wine in your pajamas.  Show her that you can look decent, even if you don’t have to.


A real simple style here. Inspired by Daniel Craig’s James Bond from Quantum of Solace, when he visits the character Mathis at his villa in Talamone Italy.   (Click Here to see the Outfit in Action) Black fitted cardigan (J. Crew 69.55), crisp white oxford shirt (express, $49.90 but watch for a sale) khaki chinos (Dockers D1, $36.99) and dark brown boots (Aldo, $90.00).  Perfect for a cool sunny day in Italy, or… a Valentine’s night at home.

* * *

Destination: Going out

Can you wear a tie with jeans?  Absolutely.  Just make sure the denim is dark, and the blazer you’ve got on is well tailored.  Alfani Red and INC both carry great casual blazers like this one ($69.98) that should look terrific after some tailoring.  Pair that with either dark denim (Gap, $54.40) or a pair of light gray chinos.  Again, a nice fitting oxford, not some blousey dress shirt, and keep the tie simple and clean (Gap $29.50).  A Wool tie is a better texture to match with denim if you’re going that route.   Don’t forget the watch, This one by Swiss Military proves that even Chronographs can come in subtle cases, and at a fair price.

* * *

Destination: Something Fancy

So you’re headed to the nicest restaurant in town.  She’s putting on a cocktail dress.  You know she’s going to look amazing and every eye in the room is going to be on her when you two walk in.  Time to step it up so you don’t look like the awkward doofus who married or is dating “up.”  You can’t argue with a well fitting medium to light gray suit.  Even at this time of year when everyone else is wearing Charcoal and Black.  Indochino (Ultimate Gray – $295.20) makes custom suits for bargain prices.  (Click here for a full review of the suit you see above)  Plus, they run sales often and are probably running one right now.  Clean slim navy tie (Brooks Brothers – $39.95), don’t forget a white pocket square, and shined up black trim silhouette dress shoes (Kenneth Cole – $148, but they can be had for MUCH Cheaper).  A simple watch completes it (Skagen $70.35), and maybe you’ll catch a few eyes when you walk in the restaurant too.

* * *

BONUS!!! – Under Everything

jockeylowrise2
Who knows what’ll happen that night. So make sure you’re not wearing an old pair of tighty whiteys. Instead, wear a pair of underwear that a woman might actually find attractive. (Jockey – $9.99 for Three)

Time is running out to order her a gift in time for Valentine’s Day.  Wait till the last minute and you’ll get nailed on express, or worse yet… overnight shipping.  Get some inspiration here.

Filed Under: Clothing, Watches, Women Tagged With: early Feb, Indochino, valentine's day, What to Wear

Continue the Conversation …

Want to share your thoughts on this article? Send us a tweet, join the discussion on Facebook, or hit us up on Instagram!

Don’t Miss Anything

Subscribe via email to get articles in your inbox or add Dappered on Flipboard. You can also follow us on Twitter, Facebook, and Instagram. Or subscribe to push notifications to get alerts immediately.

New Here?

Well, welcome to Dappered. Here are what we consider the most useful posts on the site if you're looking to put a little more effort into your appearance. Just want to see our favorite menswear products? Shop our essentials here.

Style Scenario – Valentine’s date night dressed up, going out

Style Scenario – Valentine’s date night dressed up, going out

Sharp, dark, and handsome for a nice night out.

Monday Men’s Sales Tripod – Rhone Polo & Commuter Shirt Savings Packs are back, & More

Monday Men’s Sales Tripod – Rhone Polo & Commuter Shirt Savings Packs are back, & More

There is a peculiarity about the Rhone pack deals though.

BR Factory New Arrivals (and 49% off), Seiko 5KX decent price, & More – The Thurs. Men’s Sales Handful

BR Factory New Arrivals (and 49% off), Seiko 5KX decent price, & More – The Thurs. Men’s Sales Handful

Totes, sneakers, and Nordy Rack is worth a look.

Follow Dappered on Instagram »

Men’s Fashion or Affordable Style?

Men's Fashion or Affordable Style?

Fashion is temporary and expensive. Style is timeless and affordable. Dappered® helps you work the retail system so that you can be comfortable, look sharp, and save money.

Want to share a great product? Email Us.
For a fit perspective, see Joe's measurements.
Make sure to read our affiliate disclosure.

CONNECT WITH DAPPERED

Thanks! Check your inbox or spam folder to confirm your subscription.

  • Facebook
  • Instagram
  • Pinterest
  • RSS
  • Twitter

Most Popular on Dappered

  • BR Factory New Arrivals (and 49% off), Seiko 5KX decent price, & More – The Thurs. Men’s Sales Handful
  • Style Scenario: It’s still winter. (Nothing over $100 edition)
  • The Dappered Space: 5 Essential Home Decor Items for any grown-guy’s home
  • The 2023 Valentine’s Day Gift Guide for Her
  • Monday Men’s Sales Tripod – Rhone Polo & Commuter Shirt Savings Packs are back, & More
  • Spier launches new $298 Half Canvas Suit Line – The Best Wedding Suit under $300?

Popular Topics

  • Best dress shirts to own
  • Best looking watches under $100
  • Best men’s dress shoes under $200
  • Nike Killshot sneaker alternatives
  • How to wear a suit without a tie
  • Suitsupply store review
  • Suitsupply Blue Line review
  • J. Crew Factory Thompson suit review
  • How much does it cost to tailor a suit?
  • Dopp kit essentials
  • Brown shoes with gray pants
  • Men’s style buying guide

Copyright © 2023 Dappered.com | Dappered, LLC | Dappered® is a registered trademark of Dappered, LLC

Hat tip: Magazine Pro Theme On Genesis Framework

Dappered does not collect or sell its users personal information | Disclosures: Privacy and Affiliates, Gilt.com, FTC

WPE

We work with partners that use cookies to understand how visitors use our site. Find out more.