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Following these simple principles you should have your little Chihuahua all decked out in no time! It really isn't much different than getting your Chihuahua accustomed to collar or a leash and harness. A little patience and a lot of attention will go a long way in helping your dog feel comfortable and happy wearing clothes. Article source: http://www.wikihow.com/Encourage-Your-Chihuahua-to-Wear-Clothes  
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Encourage Your Chihuahua to Wear Clothes

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You basically need a Chihuahua or just a dog you would like to dress up.

1 - Start your chihuahua wearing clothes for small amounts of time.

At first it's better not to have your Chihuahua wear their clothes for too long. You want them to get used to them gradually. It is better to start with 30 minutes to an hour of clothes wearing at first rather than a whole day. If your Chihuahua is happy in his clothes than fine but for those who aren't as sure of them you will want to keep the times short in the beginning. It's important to remember that your Chihuahua will still enjoy lots of time not wearing clothes!

2 - Be sure your chihuahua's clothes are comfortable and fit well.

No one likes to wear clothes that are itchy, scratchy, or that just do not fit well and your Chihuahua is no exception. Clothes should not be so big that they get in the way of your dogs play and normal activities nor should they be too tight around the chest or front legs. Putting clothes that do not fit well on your Chihuahua is a good way to make him decide that clothes are a bad idea. You will want to be sure that tags are not an issue and avoid anything too frilly or bulky until your Chihuahua is already used to clothes. First clothes should be little shirts and simple dresses. Think comfort.

3 - Make it positive with treats and attention.

One of the best ways to ensure success with training your Chihuahua to wear clothes is to offer treats and just fuss over them when dressed. Dress them up for fun things like outings and walks. This builds a positive association with their clothes for your dog. Even chihuahuas who do not care for clothes as much are still cooperative because they know that getting dressed means something fun is coming around the corner for them. This 'fun' can be an outing, a walk, some playtime, treats or anything your dog enjoys. Just be sure to always have a fun activity or a tasty treat ready for your Chi once dressed.

4 - Supervise your Chihuahua to redirect chewing and biting on fashions.

This can be a common problem especially when starting puppies with clothing. Get your dog dressed when you have time to spend with them. This way you can be making this a fun attention filled time for your Chihuahua AND you are available to redirect their chewing on their clothes and keep them distracted so that they just forget about them altogether since they are having so much fun with you!

5 - Tips

If possible, start young. If you have a puppy now is the time to start them with clothes. The younger you start them wearing clothes the better because young Chihuahuas will simply adapt easier to whatever life hands them. It's a gift of youth. But the principles here are the same for an older Chi too. On a chilly day or you can adjust the thermostat by a degree or two, toss a little shirt in the dryer for a few minutes and then put that on your chi. Chihuahuas like to be warm and if they a little too cold that warm from the dryer shirt will be a welcome sight. If you have a little one who is especially uncooperative at first try this for getting that shirt on! Hold a treat in one hand and your dogs shirt in the other. Hold the treat to your dog through the neck hole of the shirt. As the dog comes towards the treat, hold onto the treat a bit and slip the shirt over their head as they get the treat. You can also give a treat on the floor for each leg as it is lifted and put in their shirt too.

6 - Warnings.

Always supervise your chihuahua when in clothes. Inspect your chihuahuas clothes frequently for loose buttons, etc. Make sure that clothes fit well under their 'arms'. This is a spot where shirts can be too tight and chafe delicate skin to the point of bleeding. Chihuahuas like to be warm! Clothes are great in the winter and in the summer in air conditioning. Keep the weather in mind! Don't ever sacrifice your dog's comfort for fashion. No clothing should ever be worn when hot.

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