Vest Up with Boots and Jeans

How to wear vests, boots, and jeans in Fall and Winter

It’s that time of year again, when boots are the go to shoe, jeans in all types fill stores, and every girl brings out her North Face vest. Although I tire of seeing these three things styled all together, I do understand why they’re the “triple” threat for cold weather.


Here is a traditional way to wear a vest, boots, and jeans, but stay tuned for my favorite ways to mix up these three popular items for fall and winter.


I am wearing my favorite button up from J.Crew under a white North Face Aconcagua Vest. This year I have come to love gingham print fabrics. This button up is sold out, but you can find a similar one here from J.Crew.


I am wearing my absolute favorite rain boots from Target! They are very inexpensive and come in black and olive too. They may be one of the least expensive shoes I own, but these Chelsea Rain Boots are one of my favorite pairs of shoes. I have gotten so much use out of them. I recommend them over Hunter boots, which are quadruple the price.


This lace up lightweight “sweatshirt” from White House|Black Market fits perfectly under a lightweight vest. The laces draw your eye in (and are on trend), eliminating the need for a necklace. The best part is it’s thicker than a typical long sleeve, so with a vest it’s enough to keep me warm in cool (not cold) weather.


These boots are my favorite for this fall/winter! They’re perfect in rain, shine, and I am assuming snow! These Chelsea Boots from J.Crew Factory are 100% leather and extremely comfortable. If I could only wear one show this season, it would be these boots.



Vests are a fantastic way to add a little color to a monotone outfit. Plus, I love wearing vests with leggings. It gives me pockets for a phone, ID, and other essentials I carry with me around campus.


We’ve talked about rain boots, Chelsea ankle boots, and now lets talk about heeled boots!


I’ve had these suede, heeled ankle boots for awhile, and I get a lot of use out of them. A new way to wear jeans or leggings with zippers is unzipping them, letting them hang open to reveal the details on a cute ankle boot.



If you do not like the unzipped look, tuck your leggings in! Be sure you’re wearing black socks to match your leggings and boot.


Ankle stiletto boots work perfectly with a dress! My green dress and boots are from White House|Black Market. I Truly love heels! They make me feel more put together and confident. You should give it a try. Remember to pick a heel height you can walk in!


The best part about this dress is the lightweight, cotton material and pockets! Also, it has a slight cutout on the upper back, making it a perfect all season dress.



I love that these boots are leather, so I can wear them in the unpredictable weather. They will not get damaged in rain or snow.


Even in a thin stiletto heel, I can walk through leaves in the woods. This is an advantage of heeled boots because they keep your foot secure inside the shoe more than a typical heel.


My favorite one stop place to get shoes is actually Dillard’s! The department store offers a large selection of designer shoes in various styles for all budgets. A similar stiletto boot from Gianni Bini at Dillard’s can be found here. Gianni Bini shoes ALWAYS make me happy and satisfied. I also like these, stiletto ankle boots from Antonio Melani, another one of my favorite shoe designers.


This is an accurate depiction of how I feel in my WHBM dress and heels! Their products never disappoint and last a life time. Be sure to check out there amazing deals for the Holidays.


This last outfit reflects a traditional jean and boot combination, dressed up with a blazer and stylized with a leopard print tank.


I am wearing the most comfortable, non-comfort brand, boot from Style & Co. I recently stumbled upon Style & Co. this summer at a Macy’s shoe sale. I scored a great deal on a heeled sandal that I can work and walk in all day.


So when I found these Style & Co. ankle boots at the start of fall I knew they were a must have!


Style & Co. is sold exclusively at Macy’s. These Wileyy Ankle Boots are on SALE, so get yours before they are all gone. The boot comes in black, charcoal, cognac (wearing), navy, and olive. These boots look super cute with cuffed skinny jeans.


My favorite blazers come from J.Crew. They don’t need tailoring, come in a variety of styles and fits, and are reasonably priced. Every girl needs a blazer in at least navy and black.  Fun fact, the trendiest blazer and item for fall 2017 is a plaid blazer! All fashionistas are wearing them. Also, this spring I shared a few of my favorite, different ways to wear a blazer. 


I hope you feel like you can confidently vest and suit up in jeans and all types of boots this fall! Use my looks as inspiration to style rain boots, chelsea boots, ankle boots, block heel boots, and stiletto boots. Be sure to share your looks with me and comment with any questions. Tag me on Facebook and Instagram. I can’t wait to see how you style vests, jeans, and boots this season.

3 thoughts on “Vest Up with Boots and Jeans

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