1. UO Geo Necklace, available at Urban Outfitters for $18
2. Deena & Ozzy Snow Leopard Crossbody Bag, available at Urban Outfitters for $69
3. Cream Cambridge Knit, available at Nasty Gal for $68
4. ASOS Popper Parka, available at ASOS for $114. 34
5. Frye 'Veronica' Short Boot, available at Nordstrom for $267.95
6. DL 1961 Nina Ultra High Rise Skinny Jeans in Onyx, available at Shopbop for $178
Outdoor dates in colder seasons can be tricky, but we have you covered with a fool proof outfit; cute, practical, and sure to help ease those butterflies. Start with a pair of fitted, dark wash jeans to balance out the thicker materials you'll be piling on your upper body. Make sure they're stretchy enough so that you can move comfortably during your outdoor activity. We like the Nina jeans by DL 1961 Premium Denim. Crafted with xfit revolutionary four-way stretch, they won't be sagging around the bum by the end of your afternoon like many jeans do. A pair of trendy but durable boots are also the way to go. We can't imagine anything worse than having to fake enjoyment on a date when really, you want to be icing your feet and bandaging those blisters. So choose your shoes wisely. Frye has an array of beautiful boots meant for outdoor activities, so your precious feet will look AND feel good. Fall weather can be unpredictable, so we suggest layering. A neutral colored, sweet sweater is always a right choice. Put a light parka or surplus jacket over. It'll keep you warm but the cut isn't so bulky you'll be swallowed under the material. A nice mix of feminine and masculine, the cream colored Cambridge Knit by Nasty Gal pairs nicely with the olive green parka available through ASOS. Lastly, use your accessories to add some fun to your outfit. A cross body bag will be convenient to carry during your outdoor date, whether it be a stroll, a light hike or a picnic. We like the Snow Leopard print because it keeps things from being boring. The geometric style necklace by Urban Outfitters is also a unique and modern touch, but it's dainty enough as to not get tangled in nature. Now get dressed, deep breath and have fun!