“The first time you look at your bobsled you think, ‘I’ll never fit in there,’ but then you realize there’s lots of space,” says Canadian bobsledder Shelley-Ann Brown, who won a silver medal at the 2010 Vancouver Olympic Games. She faces similar doubts when packing for winter holidays. Ms. Brown and Maëlle Ricker, gold medalist in snowboard cross, share their competitive approach to maximizing your luggage potential.

Function over fashion

Family holidays are about bickering and binge eating, not fashion. Stick with thin layers that mix and match, expand with your gut, and pack tightly. Minimize bulky items such as sweaters. “A teammate of mine is always saying, ‘Instead of pants, pack tights,’ ” says Ms. Ricker. “You can bring 10 pairs instead of two.”

Iron it

Leave the wrinkle-minimizing packing strategies to business travellers; the holiday road warrior’s only mission is to cram in as much as possible. “Rolling is your best friend! You can get a lot more into a bag,” says Ms. Brown. Keep rolls compact with elastic bands, and arrange them to create a level surface for folded clothes – pants, sweaters, dress shirts and dresses – which go on top. Hey, 45 minutes of ironing at your destination will burn off a shortbread cookie.

Choose dark colours

Never mind the madness of wearing white to a table laden with gravy and chocolate. Are you really going to do laundry once the turkey coma kicks in? “Darker clothes hide the dirt better!” says Ms. Ricker. “You can get away with wearing things longer before you wash them.”

Long underwear delays the need to wash outer layers and rolls up tight, so pack lots. Oh, it’ll keep you warm, too.

Stuff shoes

For most holidays, you need just one pair of comfortable walking shoes or boots and one dressy pair, plus athletic footwear if you plan to work out. “Shoes go in the bottom of your suitcase,” says Ms. Brown. “Lay them on their sides and jigsaw them together. You can make up the space they take up by stuffing them with other things.”

Wear it

If you don’t look like the Michelin Man, you’ve put too much in your suitcase. Ms. Ricker layers up, and always wears her boots on the plane. “I can flip them off if my feet get too hot. I bring my biggest sweater and jacket on board as well.”

Redistribute weight

Have you maxed out the allowable carry-on weight? Ms. Brown watches weight limits for checked pieces, but sometimes takes chances with her carry-on, where she stows heavy gifts (leave them unwrapped for security checks). “When you walk up to the check-in counter, you have to look like your stuff is light and walk confidently.”

Look for loopholes

“Now, this is only for serious, advanced packers,” says Ms. Brown. (Step aside, freewheeling snowboarders.) “Put your backpack strap around your waist, then loosen it and you’ll create an extra space. Roll things and place them there. Technically, you’re wearing it, not carrying it.”

And don’t do this … Bring sweaters if you can borrow.