From Boxer Briefs to Bikinis: A Beginner's Guide

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Boxer briefs are the comfort zone. Bikinis can feel like a big jump, but they don't have to be.

Why guys make the switch

  • Less fabric bunching under trousers
  • No legs riding up
  • Lighter feel in warm weather
  • More style choices (color, print, cut)

Step 1: Start with a brief or a "hipster brief"

A full-cut or low-rise brief is the bridge. You'll get used to open legs while keeping coverage.

Step 2: Move to a bikini (mini brief)

Lower sides, lower rise. Pick a soft, stretchy fabric like modal or microfiber for your first pair. See our fabrics guide.

Step 3: Try a tanga

When you want less on the hips, a tanga swaps the side panel for a narrow solid band. See our styles guide.

Fit tips

  • Size by your waist where the underwear actually sits, not your trouser size. (Obviously's chart, for example, says to measure "where your underwear normally sits.")
  • Low-rise cuts sit lower, so check the brand chart.
  • A contoured pouch makes a big difference in comfort.

What to wear them with

Slim chinos, gym gear, swim season, or nothing in particular. They're for you first.