A Successful Valentine’s Day Starts with New Underwear

On Valentine’s Day, your underwear doesn’t have to be red or purple or have little tiny hearts all over the front—although, to be clear, we fully endorse those moves—but it does have to fit you well and look fresh. If you’ve been wearing your underwear for more than three relationships or three years, it’s time to move on. Guilty of holding on too long? Use the upcoming holiday of romance as an opportunity to edit your underwear drawer and stock up on new styles.

The number of pairs you wind up with in the end is a personal choice, but we recommend having a three-week supply, or about 20 pairs, in your rotation. That stockpile will allow you to refresh your underwear after the gym for example, or skip laundry day if you’re having an especially lazy Sunday, but it won’t overload a small drawer at the same time. It’ll also give you an opportunity to buy a few different styles, colors, and patterns to suit any wardrobe or activity. Here’s a checklist that covers all of the bases, plus some storage suggestions that’ll keep your drawer looking nice and tidy.


The Express Men’s Guide to the Ultimate Underwear Wardrobe


Sport Trunks and Boxer Briefs (12 pairs)

These are your go-to, everyday underwear. Buy the length of your preference or have both options on hand. And be sure to mix up the colors, too. You’ll need a few solid neutral colors in varying tones. If you aren’t afraid of a little color, fill in the gaps with some unexpected stripes, bright hues, and bold prints.



Boxers (2 Pairs)

Unless you’re a 24/7 boxer kinda guy, you only need a couple of pairs of old school shorts in your rotation. Wear them under baggy chinos on errand-running day or during a particularly laid-back morning when you have no intention of putting on pants at all. Plaid is a classic choice—especially this time of year when the cozy vibes are turned way up.  



Extended Boxer Briefs and Performance Briefs (5 Pairs)

If you’re pretty active, you’ll want a pair of moisture-wicking, stretch briefs or boxers handy for your daily sweat session (fewer if you don’t make it to the gym quits as often). Our extended lengths are convenient under basketball shorts or when you’re running outdoors and need some extra warmth.



3 Essential Underwear Pro-Tips

1. Buy an Organizer

Buy or build an organizer for your drawer that keeps each pair in its own cubby, then organize it by color or style for easy access in the mornings. You’ll never reach for the wrong pair when it’s laid out like this, we promise.

2. Keep ‘Em Spiffy

Roll or fold your underwear instead of stuffing it into your drawer so that it looks as new as it (hopefully) really is. You’ll get that fresh-from-the-laundry feeling when you put them on that way, too.


3. Repeat with Your Sock Drawer!

If you’re taking the time to revive your underwear drawer, you might want to wrap your head around your stash of socks while you’re at it. Roughly the same rules apply. Three-week supply, a mix of everyday and sport styles, plus a few outliers. Paisley, anyone?