Holiday Wardrobe Help Every Mom Wants and Needs

By Lisa Dickstein, Personal Shopper and Closet Editor November 11, 2019

It's warm. Oh, wait. It's cold. This weather, as beautiful as it is, is posing a daily challenge as to what to wear. Amiright?

I am here to help ease the transition and navigate the 29-degree temperature swing that seems to happen in the space of 2 soccer games. Here are my top three rules for transitioning your warm-weather wardrobe to a cooler-weather wardrobe.

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Rule 1: Layers, layers layers.

As the mornings and evenings cool down, you should have a layer ready, depending upon your activity. These pieces can be a thin sweater, long cardigan/duster, denim jacket, lightweight bomber jacket, long sleeve shirt or a leather jacket. The possibilities are endless. My hardest part is deciding which one to grab on the way out the door. It definitely might be a good idea, when you have a free few moments, to dig through your closet and see what you have and what pieces you need to fill in. This will make it much easier when time is tight.

Rule 2: Make sure you have solid base layers. 

This can include a clean, crisp white tee, a cheeky tee/tank or a lightweight more fitted long sleeve. The same goes for evening events; a lacey camisole, colorful blouse, turtleneck, strappy tank, etc. You need to make sure that should the temperature go up and down (and it will) that you are comfortable taking your outer layer off as well as feel put together when you throw it over your look. This is a good time to weed out those dingy looking “white” tees as well as any shirts that may have seen better days.

Rule 3: Fall is a great time to try out a myriad of choices for the bottom half. 

Of course, you usually can’t go wrong with jeans. Many different styles are trending from straight leg to wide leg and many in-between. The key is finding which style fits your body in the most flattering and comfortable way. Joggers are great options as well. I carry options from the softest cotton to pair with sneakers, sandals or booties to velvet trimmed in satin to pair with heels. They are super versatile and usually super comfortable. Of course, there are also the workout leggings, cargo skinny, tailored pants, cords, skinny pants, sweats, skirts (short, midi & long) and dresses.

As you can see there are so many options, it can be a daunting task just to get dressed. Go through your closet (or let me help you) and find your go-to pieces. Those you can pair with other things you already own. Also, look to see what you may be lacking as the temperature drops. It’s time to put away those super thin summery pieces and change things up for the next season. Slightly heavier fabrics, mixing darker clothes into the mix (plenty okay to pair pale pink or pale blue with navy, black, dark purple, chocolate brown). Fatigue (army green) pants are another staple that pretty much goes with everything! I also love camel and white paired together year-round. You can most certainly wear white after Labor Day.

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or personal shopping with Lisa Dickstein

Lisa Dickstein is a local Annapolis mom, personal stylist, and closet editor who can work with any budget to help you find a wardrobe that makes you feel and look effortlessly cool, comfortable, stylish, and put together. For more information on her services, Lisa can be reached at and can be found on Instagram here.