Looking good and feeling good in what you are wearing is just as important on the road as it is at home. We all want to look good and dress appropriately for what we are doing. When traveling, this is not only possible, but it does not require that we travel heavy. Even for a week-long trip, it is usually possible to limit everything to a single suitcase and one carry-on item without any problems.
The same rules for looking good apply while travelling, just like they do at home. Sweatpants and hoodie do not miraculously become good looking just because you are travelling - a fact that some of our fellow travelers would be surprised to learn. Instead, it is possible to dress very similar to normal.
LAYERING
The difference is going to be in layering. When traveling, it is not uncommon to experience extremes of hot, cold or both. To be comfortable in the full range, use a system of layers.
The base layer should be a comfortable, non-bulky outfit. This could be jeans and a decent shirt, a dress and a comfortable top, or slacks and a dress shirt. The key here is that it should be comfortable in room temperature or the hottest outdoor temperature you will be travelling in.
The second layer is an insulation layer. It is only needed if you will be somewhere cold. For example, a second layer is not needed when travelling by jeep between central African nations. It will be needed if in New York in January. Match the thickness of the insulation to this temperature. For informal travel, I recommend fleece as it is warm, looks good and is not super bulky. A suit jacket or a sweater are also reasonable insulation layers.
The top layer needs to be weatherproof. This can be a rain jacket or wind-breaker in warmer climates. Colder climates can range from a wool overcoat to a ski jacket. The key here is to keep any bad weather away from your inner layers.
This strategy is useful when planning any activity, not just travel, that will involve being outdoors. It is important for travel because layers give you the ability to adjust as necessary to meet the changing conditions. Lastly, all of these clothes should be in good shape and clean. This should not be a necessary warning, but you will meet travelers who do not heed this.
QUANTITY
When traveling, it is important to minimize how much you bring with you. This means taking time to plan the wardrobe carefully. Unless there is a known reason to bring something significantly more or less formal than you normally wear, do not bring it. If you pack everything at one level of formality, it is easier to pack fewer complete outfits. Shoes are especially important here. Having a single pair of comfortable shoes that can be used with all packed outfits does a lot for reducing the bulk of clothes to be packed.
Even travelling by air and domestically, having more than one suitcase can be problematic. Even if the checked luggage makes it on to the save flight as you, it could come damaged. Even undamaged, you need to carry, pull or drag those bags around with you at your destination. Plus, you have to wait at check-in to hand over the bag, wait at baggage claim at the end, and if anything goes wrong, you can be stuck without your luggage. Most bags do not experience this problem, but it happens regularly enough. Buses, trains and other transport can be even more limited in available space.
For most trips less than a week in length, it is possible to pack enough comfortable, good looking clothes into a single carry-on bag. Any bulky items - like coats or jackets - can be worn or hand carried onto the travel vehicle and used throughout the trip. One complete change of clothes a day is reasonable, but even this figure can be cut down if you will wear parts of an outfit more than once or will use a laundry service as necessary.
COORDINATION
Wearing clothes more than once is not an issue when the wardrobe is chosen carefully. Durable clothes that do not stain or wrinkle easily are a necessity. Even if not worn twice, accidents happen and wrinkles happen easily inside a suitcase. Sometimes part of an outfit will be wearable and the rest is not.
Choosing clothes that can be mixed overcomes this issue. Being able to grab any top and any pants and use them as a matching outfit gives a lot more flexibility to a small wardrobe. This flexibility can help keep you looking good while reducing the size of your luggage.
SUMMARY
As you can tell, I subscribe to the group that aims not to check bags during travel whenever possible. It has worked well for me. With coordinated outfits in my legal-sized carry-on bag, and an established routine I breeze through security checkpoints without any problems. My luggage always gets there with me.
This has worked for trips up to two-weeks long without needing to launder any clothes. Minimizing the clothes also makes it easier for me to bring other extras along - books, DVD player, etc - for use during the trip. For longer trips, I do plan on having clothes washed, which lets me continue to get by with a single carry-on bag.
If you are having problems looking good while trying this strategy, just revisit the basic ideas. Choose good looking, low bulk, comfortable clothes. Match them so they can be mixed up. Keep the layers in mind. Be willing to wear items more than once or have them washed as needed. Limit the number of shoes, sweaters, jackets and coats.
Learn to travel light, wearing comfortable and good looking clothes and you will never want to go back.