All four of your outfits are fabulous.
Outfit #1: Far from meh. I love those burgundy pants. They pair so well with that grey sweater, and the boots, too. That color makes sense for the flowers, and the pants being somewhat dark allows the lighter color of the boots to stand out. This is a great outfit for weekend casual, casual yet looks soooo nice at the same time. You look great.
Outfit #2: Very lovely. The skirt with the colorful prints is the standout piece, with the solid black top and boots. I like that you have some of your hair pulled in front of you, as the black top, being so dark, flatters it very well. Your hair is quite pretty, and deserves to be shown off by a top like that. I love those boots, too, especially tall ones like that with a midi skirt. My adjective for that look would be classy-conservative. It is a wonderful winter look. I like that necklace, too, it also adds elegance to the look. You look ready for going out to dinner. You look lovely.
Outfit #3: I love the "professional" vibe I get from this look. This is a great look for an office type job. The jacket obscures a lot of the prints on the top, but it looks grand on you, and so does the blazer. The top and blazer pair so well together. Then, it appears as though you are wearing slacks or trouser pants. The black, with its contrast, helps the blazer and top to stand out. Then, I'm loving those boots, yet another professional-looking element to your look. The heels add a little class, too. This outfit makes you look powerful, ready to take on corporate America. You look fabulous.
Outfit #4: You are unsure about this one, but I have to say that I think this one is my favorite of the four. The only reason I say "I think" is because the other outfits look so good, as well. Even though it's one solid color, that dress is so so very pretty on you. I like that you chose black for the cardigan. By the black blending in, the flowers add to the dress, rather than the cardigan competing with the dress. That was great styling there. Plus, like in outfit #2, the black is flattering to your beautiful hair. I like the black tights -- by the way, are they tights / nylons, or leggings? I probably would have chosen neutral tights or a lower den to create a break with the dress, but I am liking your choice of the black better, as they show off the boots better than my choices would have, especially with the dense opacity. Great styling there. Love that combination with the tall boots. The heel really dresses up the outfit, and you have given your outfit a great "endcap" effect, with the boots and your hair being very close in color. That necklace adds a little elegance to the look, as well. You look awesome, totally ready for a night out on the town.