captoe boot

What to Wear for Your Valentine’s Day Date

Are you ready for Valentine’s Day, gents? Got the reservations? Prepared the gifts? Awesome. Now all you need to think about is your outfit for the day. As much as sneakers and hoodies can be mixed and matched for fashion-forward street style ensembles, there are just certain occasions when it’s better to leave them in the closet; Valentine’s Day is one of those occasions. Here’s a V-Day outfit idea that your date will appreciate:

1. Start with a crisp shirt. Make sure it’s form-fitting, and any wrinkles have been ironed or steamed out. By no means are you limited to a white shirt, but this tends to work well with a variety of color combinations.

Zara Plain Tailored Shirt

2. Add a tie to your ensemble to get extra dapper points. If you’re going on a more casual rendezvous, skip the silk tie. Instead, try a woven or wool tie so you don’t look inappropriately formal for the date. 

1901 Knit Tie

Alexander Olch The Partt Plaid Necktie

3. Layer with a cardigan for warmth. Avoid colors that contrast too much and would look awkward with your shirt or jacket. Feeling trendy? Go for a shawl cardigan! 

Theory Dotted Cardigan

John Varvatos Star USA Shawl Collar Cardigan

4. Top it off with handsome outerwear. A sharp blazer that fits perfectly won’t fail you. If your Valentine’s Day weather will be too cold, try something like the Jack Spade hybrid blazer with quilts for extra warmth, or opt for a coat instead.

Banana Republic Tailored-Fit Charcoal Twill Blazer

Jack Spade Bentley Hybrid Blazer

Rag And Bone Eccleston Jacket

5. Slim pants or jeans will give you a clean-cut look. Jeans with light washes are great casual staples, but go for dark washes if you’re going to upscale venues. 

Tailored Laundries Casual Pant

Topman Slim Fit Jeans

6. Don’t forget the details: a nice classic watch and belt. You don’t have to go over-the-top with the style; keep it simple- brown with brown, or black with black. 

Brooks Brothers Round Watch with Calfskin Band

Uniqlo Vintage Belt

Daniel Wellington Sheffield Watch with Black Leather Band

Shipley & Halmos Oak Belt

7. Complete the look with polished shoes: a nice derby or oxford, or if the 14th will be rainy or snowy for you, a boot.

Aldo Manzella Captoe

Aldo Orme Wingtip Boot


Be a Valentine’s Day prince for your special someone. Need more outfit ideas? Check out the men’s Valentine’s date night style feature on Wantering. Have a fun!