What To Wear On Your First Day Of College, Because First Impressions Are Important Chambray Shirt. Button up says professional, but the chambray texture makes it way more laid back and off-duty than a classic, white blouse. Skinny Jeans. A Denim Skirt. Short Sleeved Blouse. A Bright Dress. A Denim Jacket. A Vest. Pixie Pant.