The trick to staying warm while traveling is layers. Next to skin you can go with something synthetic like any running/work-out top or merino wool; a sweater or, light insulted jacket for warmth and/or when the weather isn't wet or, blustery and when the things get wet, you can throw on a light-weight shell.
While synthetic base layers are inexpensive, I'm not a fan of the clammy-sensation you get after wearing a synth shirt/bottom all-day, Merino wool gives you a nice warm layer that doesn't cool-down too fast and the smell-factor with synthetics aren't an issue with wool; something to consider when laundering in your room. The major brands in this arena are Smartwool, US brand good overall value and designs, Icebreaker originally a New Zealand brand, a bit more sophisticated in design and Ibex, US brand out of New England. Uniqlo is a Japanese-brand similar to the Gap, they actually use many materials similar to major technical outdoor brands but at reduced prices, check-out your local mall as they're always worth a visit, particularly for basics/components. I like having a couple of t-shirts (S/S and L/S) made of merino wool, they work as base-layers and look fine if worn alone. A zip-neck or, turtle-neck made of merino also makes for a mid-layer/nice sweater.
Mid-layers for warmth, I like a light insulated jacket. Down is great because it's really compressible but, synthetics are popular due to their near mimicking of down and their price isn't as high as down. Patagonia's NanoPuff Jkt and The North Face Terra Jkt I really like and are quite popular; every outdoor brand has a jacket or two in this category so, there should be one out there for you to choose. Shells, a basic lightweight rain jacket will suffice Marmot PreCip Jkt, The North Face Venture or, Alta Vista Jkt, Patagonia's TorrenShell...all are good, durable and popular styles for travelers that come in a range of colors to fit your style. If you're price sensitive, Uniqlo does a pretty good job, Eddie Bauer and Costco occasionally has a few gems, and don't forget LL Bean and Duluth Trading Company.
As for luggage, really comes down to what you're comfortable with, IMHO I find the RS travel luggage to be very basic and unsophisticated, this helps keep costs down, not the most attractive and a bit lacking in features or details but, it gets the job done. Rollers (2 wheels) and Spinners (4-wheels) are very popular, if you're able to travel with a small backpack and a roller-board you're all good; I'm a fan of Briggs+Riley, others really like TravelPro, Tumi, Samsonite and others. I prefer to pack my clothing in packing cubes, this helps keep things organized; I'll also pack drier-sheets in a ziplock to help manage luggage smells and a small laundry bag and a few clothes pins when its time. Travel packs have seen a resurgence in popularity as the feature set available are more appropriate, and its nice to be hands-free as you roam around a new destination. Osprey is one of the market leaders, Cotopaxi has fun with their colors, Thule, Aer, Tortuga, Peak Design, Evergoods are all really good brands with smart designs and carry options.