I tried the"clip on" kind that pinch your nose but they wouldn't stay on. There was a small learning curve (exhale completely through mouth) but these worked for me: http://www.sinussaver.com/

How can he swim with a nose plug?!

Have him stand in the shallow end and practice leaning forward and putting his head underwater looking straight at the bottom of the pool, continuously exhaling through the nose and mouth, and rotating to inhale through the mouth, repeat. Just like swimming but standing in the shallow end so he doesn't panic for air. Once he's comfortable with that (water no longer coming up the nose) then he can try to do the same while swimming. He's got to be the worst swimmer in the world if he can't stick his face underwater without a nose plug????

I always use plugs. Some of my friends give me crap about it but I just beat them out of the water and they can suck it.
The two that have worked the best for me are the speedo brand like this one. http://www.team-aquatic.com/...ition-nose-clip.html
and the one with the strap like this http://www.swimoutlet.com/...-clip-w--strap-3949/.
I have had them knocked off in a race so you still need to know how to swim without it. But it's so much nicer to not have to deal with water up the nose when I flip.

I bought a nose plug (http://www.sinussaver.com/) toward the end of last season, but haven't used it yet. I have really bad sinus issues after open water swimming. I don't have the same issues with chlorine.

The super ugly old school tan ones with the metal nose bridge worked best for me, sadly I can't find them anywhere any more so I'm looking for a good replacement.

I get sinus infections if I swim without, especially in open water, so I always swim with them.

I like these speedos.
http://www.swimoutlet.com/...nose-clip-22104/?q=1

I wear these upside down with the pads pinching my nostrils shut and the arch going under my nose. With the hard plastic, I can rough the pads up with sand paper if they are not staying put.

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Oui, mais pas de femme toute de suite (yes, but I am not ready for a woman straight away) -Stephen Roche's reply when asked whether he was okay after collapsing at the finish in the La Plagne stage of the 1987 Tour

My experience fwiw...

I can swim with no plug/clip but at least a little incidental pool water gets in the ol' schnoz and I turn into Ronny Runny nose with a side order of phlegmy Phil for about 24hrs. I'm guessing I'm more sensitive to the chems than most.

So, in the pool, I use a cheap CVS store hard white plastic u shaped clip. If they come with a neck strap I cut that off. It keeps the water out for me, better than fancier models. I blow out a little air through my nose while swimming with the clip if I'm working hard. Takes no time to get used to breathing mouth only. Looks goofy I suppose but worth it.

If your bro isn't bothered by chlorine, maybe a clip could be a temporary thing, you know, baby step it until nose exhaling under water becomes automatic.

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The Ride of Truth - OWN your ride.

I have a pair of those and cannot get them to stay on. I tried the arch under my nose and that didn't work. Clearly we have different shaped noses!

I initially had that problem, so I took a knife and cut grooves in the part that contacts my nose perpendicular to the direction the plug was sliding off. In subsequent testing, I have found that if I scuff up the part that contact my nose with some course sandpaper other abrasive material, they stay in place.

Two other things that have helped the nose plug stay on are a quick wipe off of the grease on my nose with a towel and to practice not flaring my nostrils while sucking air.

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Oui, mais pas de femme toute de suite (yes, but I am not ready for a woman straight away) -Stephen Roche's reply when asked whether he was okay after collapsing at the finish in the La Plagne stage of the 1987 Tour

I have had several surgeries on my nasal canal and due to them I use a nose clip when swimming. A swimmer my whole life never used one before my surgeries. My first one was in 2006 and was required to not get water up my nose for 6 months. I stopped using it after that. Water enhanced further issues and required more surgery. I use one all the time now. I hate it but it's far better then the alternative. I use the speedo liquid comfort one nose clip. They have been the best I have found. They stay on relatively well and don't kill your nose. I used one for my last full Ironman and it worked great.