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The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall

Yesterday when I walked out of my apartment for a morning coffee run, it was a blissful and bright 80-degree day. By the time I returned home later that night, I had acquired two more impromptu layers due to the evening chill—a long-sleeve tee and a leather blazer. If this situation perfectly illustrates what you’re going through right now, you’ll want to bookmark this article and give this transitional checklist your full attention.

Right now, we’re at the crossroads of summer and fall, and besides wondering whether to order a cold brew or cappuccino, the great debate centers around the right time to retire all those linen dresses and finally break out an autumnal knit. It’s a tricky predicament, but it doesn’t have to be so complicated if you have the appropriate pieces at the ready. Presenting: the transitional-wardrobe checklist. From cozy-yet-not-too-warm knit tops to airy maxi dresses, I’ve compiled a list of everything you need to breeze through the late summer/early fall phase effortlessly—all under $40. Keep scrolling to check out everything and to see how to style them for the season.

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall
At a certain point, in order to get through the day without completely freezing or burning up, a comprise needs to be made between hem and sleeve length. This dress keeps you breezy on top yet toasty on the bottom.

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall - www target fall items 294922 1629815570257

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall
And if you’re all about streamlining your closet, getting it in black is always a wise choice.

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall - www target fall items 294922 1629815728204

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall
This toasty caramel is right on tone with chilly fall days. To keep your legs even warmer, add a pair of knee-high printed boots.

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall - www target fall items 294922 1629818137082
The type of top that can work with denim shorts or leather pants.

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall
The shoulder design elevates this beyond its $33 price tag. I can already tell this will be a go-to sweater in my lineup.

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall - www target fall items 294922 1629818060963
I’m already thinking about pairing this with my favorite pair of chunky lug-soled Dr. Martens. But until it’s full-fledged boot weather, minimalist sandals will do.

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall - www target fall items 294922 1629817548042
Style tip: Buy this in multiples. 

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall
Including this creamy beige.

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall - www target fall items 294922 1629816998133
This isn’t just any T-shirt. It’s a cool T-shirt complete with a dramatic puff sleeve.

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall
This colorway really pops against darker denim washes.

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall - www target fall items 294922 1629818035289
When the temps cool down, faux-leather trousers are a must. 

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall
It may feel a little overzealous to dive deep into oversize sweaters in August, so here’s a cute knit cardigan to help you out.

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall - www target fall items 294922 1629817727057
Wear this off-white version with cutoff Bermuda shorts and boots for a low-key transitional fit.

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall
This shade of green is also coincidentally trending right now.

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall - www target fall items 294922 1629817802349
Since the tailored look is always in, a pair of polished pants like these are a sound investment.

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall - www target fall items 294922 1629817855732
Another delicate-meets-grunge dress I’ll be wearing until infinity.

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall
If you’re returning to the office this fall, you’ll need a versatile pair of work pants. Yup, these are them.

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall - www target fall items 294922 1629817999656

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall
On the topic of compromising hems with sleeve length, it’s still possible to pull off minidresses in early fall—just stick with long sleeves and darker prints to make it work.

The Transitional-Dressing Checklist: 20 It Items That Exude Big Fall - www target fall items 294922 1629818175798
How expensive does this top look?

Next up, Comfortable and Chic Skirt Sets Are the New MVPs in My Closet

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