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Fall’s biggest fashion dilemmas — solved

Transitioning from one season to another can be tricky when it comes to your wardrobe. Between knowing what to buy, how to wear it and what’s worth keeping from last year, getting ready for fall can be frustrating. To help you start the season off right, we’ve rounded up some of the biggest fashion dilemmas and share some tips for how to deal.

Woman wearing fashionable fall outfit

We turned to Michelle Madhok, shopping expert and author of the new book Wear This Now, for her tips on how to solve some of fall’s biggest style dilemmas.

Fall style dilemma 1:

I don’t want to spend a fortune updating my wardrobe for a new season. What should I do?

Before you start dipping too deeply into your wallet, take stock of what you already have. “In our book, Wear This Now, we talk about how to update your wardrobe for each new season without breaking the bank, and guess what? It all starts with taking inventory of your closet and whipping it into shape with some old fashioned organizing,” affirms Madhok. You need to know what you already have — what still works and what can be edited out, so you can have perspective. She refers to this as “shopping your closet.”

By taking a hard look at the contents of your closet, you’ll be surprised how many outfits you’ll find. “The best part is that after you organize your closet, you can see everything you own, and once you weed out the pieces that are no good, everything in your closet is instantly wearable,” Madhok says.

Fall style dilemma 2:

The weather is so unpredictable. One day it’s warm, the next it’s cool, so I don’t know what to wear.

Layering is key when it comes to dressing for whatever Mother Nature decides to come up with as the seasons shift. “Make sure you have a few good quality tank tops, silk shells, camisoles and tees, along with quality cardigans and jackets that can be mixed and matched,” advises Madhok. “Scarves come in a variety of prints and are often inexpensive, so you can stock up on a bunch of them. They’re stylish and warm, but also easy to remove.”

Fall style dilemma 3:

I’m overwhelmed with choice when it comes to fall shopping. What are the key pieces I should focus on?

When it comes to fall shopping, especially if you’re stumped on what to buy, focus on the items people will see the most, advises Madhok. “That means an amazing pair of booties or boots that you can walk comfortably in, great silk blouses for work and weekend, a great jacket in a texture — velvet and burgundy are huge trends for fall, and a new handbag,” she says. “Try a bright color this year or get into the color block trend.”

Fall style dilemma 4:

I still like most of my fall wardrobe from last year. What can I do to refresh what I already have?

To refresh the wardrobe you already have, nothing is better than statement jewelry. “No one will remember you wore that black turtleneck all of last winter; they’ll be too busy staring at your awesome collar necklace,” notes Madhok. Belts can work wonders, too, she advises. “Throw one around a cardigan or a dress and you’ve got a different look, and we can see your figure, which is a nice bonus and can even make you look like you lost a few pounds.” If you’re looking to buy just a few items for a new season, Madhok suggests going for pieces that will make a big impact. “A great pair of leather boots and some statement jewelry can take last year’s basics to a new, updated level.”

Watch: What is pre-fall fashion?

For a style that will take you from summer through fall, Jill shares what to expect from pre-fall fashions.

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