Marcus Kirby
by Published on September 7, 2019

To be honest, when I first thought of reaching out to my sisters and friends to help them with their fall shopping needs, I thought it would be a breeze. After all, it makes sense that finding certain things on the highly saturated e-commerce space could be hard for the average consumer, but me? I’m a pro! How long could it really take for someone who does this all day for a living?

Well, folks, the answer is quite a while! From my sister Tiffany’s dresses-to-wear-with-boots request to my friend Lauren’s need for cool maternity wear, I understand why they had to ask for help because it seems that some fall finds don’t even come easily to me. Nonetheless, I couldn’t leave them high and dry, so I persisted. To see and shop the seven things I found for them (and now you), just keep scrolling.

"For fall, I need (at least) one good pair of comfortable ankle boots I can run after my kids in all day but still look good." — Jessica, sister 

Not only are these knit boots comfortable, but they are very in line with fall's military-inspired trend, so you know this is a good buy.

These Proenza boots are a great way to break up an all-black outfit. Plus, they zip from the side, so you don't have to deal with the laces when you're in a rush or on the go.

If (like me) you prefer a boot with some height, look for something with a block heel for extra comfort. 

"I read somewhere that it's going to be in style to wear a sweater with another sweater wrapped around it. I don't know if they're making decoy sleeves to tie over your shoulders or if people are just buying two sweaters to wear together or what, but I need help figuring that out." — Alanna, friend 

It doesn't get easier than this.

You can always count on Mango for an under-$100 take, and I love how this looks like a short-sleeve sweater styled over a tonal long-sleeve.

Leave it to Jaquemus to put its own spin on the trend with this halter-tie situation.

"I love wearing dresses all year round, but it's always hard for me to find ones that look good with boots for fall and winter." — Tiffany, sister 

A dark floral makes everyone's favorite summer dresses suddenly perfect for fall. 

This knit dress will look perfect with knee boots.

Topshop has the right idea styling this with a sleek pointed-toe bootie.

"I'm three months postpartum and still getting back into the swing of non-maternity dressing. I need some good transitional pieces that are flattering but still on trend for fall." — Jamie, friend

A long coat styled over a monochromatic outfit is my go-to flattering look for fall and winter.

Hemlines are getting longer, and a sleek pair of dark jeans paired with a low heel is the leg-lengthening combo we all need. 

A belted jacket will always make your outfit more flattering by adding definition to your waist.

"I need stackable, gold necklaces. It's so hard to find ones that will look good all together!" — Negar, friend 

The clasp on this necklace goes around any link, so you can customize the length based on what you're wearing it with.

Adding an additional element besides gold, such as a pearl, will give your necklace stack some life.

Varying chain sizes and types is important for the look as well as avoiding tangling, so be sure to opt for different styles when shopping.

"I need help finding clothes for pregnancy that are still trendy and cool." — Lauren, friend 

This roomy Ganni skirt is both comfortable and on trend.

Nanushka's cozy knit dress is literally expandable and can be worn countless times with any shoe style of your choosing.

A leather dress or skirt may feel restricting during pregnancy, but you can still feel on trend in this layerable shirt.

"I have a few weddings and engagement parties coming up and am having trouble finding cocktail dresses that are unique and flattering." — Jen, friend 

Feathers are definitely unique, and this slip style is so flattering.

You can never go wrong with an LBD, but this one is especially chic.

The ruched front here is adjustable, so you can DIY the best fit for your body.

Up next? The three fall sweater trends you should know before shopping

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