September is such a weird month. It’s that odd not quite summer not quite fall in between moment. You never know if you should fast forward into fall fashion or continue to embrace the current season until it’s bittersweet end. To make it even more difficult, it almost never feels like summer in New York after Labor Day even though the official end isn’t until late September. To that end, I love love love mixing clothes together from each season. This is seriously the only time that I can seamlessly (sans tights) mix boots and shorts, sweaters and shorts…really anything and shorts. Clearly I love shorts!

Two staples that I always have ready are this lightweight military jacket and my trusty Chelsea boots. I bought the jacket a few years ago while shopping with my girls at the cutest boutique in San Francisco. It’s so soft and easily a perfect topper for chilly days. My Chelsea boots make it so easy to traipse around the city, I really don’t know how I functioned before I got them. They’re my rain boots, my walk about town boots, my “my feet hurt, where are my flats”?” boots, my everything boots.

Versatility is exactly what you need this time of year and you can never go wrong with these wear with everything staples. Even though these are not new to my closet, they do get restocked each year because they’re so popular. I guess I’m not the only one who loves the classics. Be sure to check them out at the links below!

What are some of your favorite transition pieces? Drop me a note!

Dashing D
Outfit Details 

Top F21/Shorts old/ Jacket Azalea/ Boots J. Crew/ Hat H&M/ Sunglasses Ray Ban/Bag old 



  1. As usual, I enjoy reading your blog and love the tips. I often get some if my inspiration from you. I’m loving the criss crosd cami. Haven’t seen them before. Love the mixing of the seasons also. Very diverse. Shorts I can’t do but what do you think of short skirts instead 🤔


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