What to Buy in August: Fall Transition Wardrobe Guide

Every August, I go through the same cycle. I start eyeing fall clothes online, step outside into 95-degree heat, and immediately regret every sweater that caught my eye. Ten years of doing this and you’d think I’d have learned by now. I haven’t.

But here’s what I have learned: August isn’t the month to overhaul your closet. It’s the month to buy a few smart pieces that work right now and quietly become your fall favorites later. Below are the categories I always tell readers to shop first, and why each one earns its place.

Two Outfits I Actually Tried On This Month

Reading about different styles is one thing, but seeing them on an actual body is what makes a buying guide useful. Here are two combinations I tried recently that show these ideas in action.

A Printed Blouse That Bridges Summer and Fall

This one surprised me. I’ve disliked barrel-leg jeans for a while now, on me, the exaggerated leg has always felt like it was wearing me instead of the other way around. But the Johnny Was Ryan Barrel Jeans changed my mind. The leg shape here is much more subtle than other barrel styles I’ve tried, so it still gives that relaxed, of-the-moment silhouette without swallowing my frame.

I paired them with the Johnny Was Loubellah Blouse in a medium, which is exactly the kind of print-heavy, lightweight top I reach for in August. It has real presence on its own, so I kept everything else simple, tucking it loosely into the jeans and letting the sleeves stay a little billowy. On my feet, my NAOT sandals, I always size up in these, and they’ve become my go-to for walking comfort without giving up a polished look.

This is a good example of a transitional outfit done right: one piece with personality (the blouse), one piece that’s more versatile than it looks (the jeans), and shoes that work whether it’s 95 degrees or the first cool morning of fall.

A Cozy Neutral for Cooler Days Ahead

For a cooler, more pared-back look, I tried the Tommy Bahama Surf Shore Basket Stitch Crew Sweater with the Tommy Bahama Boracay Beach High-Rise Ankle Jeans. The basket-stitch texture on the sweater gives it visual interest without adding bulk, which makes it a good layering piece once it’s actually cool enough for a jacket on top. Keeping the jeans in the same neutral family as the sweater made the whole outfit feel more polished than jeans-and-a-sweater usually does.

This combination is proof that “neutral” doesn’t have to mean boring, the texture is doing all the work here, which is exactly the kind of texture-over-color thinking I mentioned above with tops.

For reference, I’m 5’6″ and typically wear a medium or large in tops and a size 8 or 29 in jeans and pants, so I’ve noted fit details with that in mind.

Start With a Layer That Does Double Duty

The biggest mistake I see women make in August is buying a heavy sweater because it’s on sale, then not wearing it until November. The better move is a lightweight layer you can throw on the moment the air conditioning gets a little too enthusiastic, but that also holds up once the weather actually turns cold.

Look for: a short denim jacket, an open-front cardigan, or a lightweight barn jacket. All three work over a summer dress right now and over a long-sleeve tee in October.

Talbots Refined Denim Short Jacket

A short denim jacket is a category I return to every year; the Talbots Refined Denim Short Jacket is a great example. It hits at the hip rather than the waist, which flatters higher-rise pants and dresses alike, and denim never really goes out of style. If you like a closer fit, size down, jackets like this tend to run a little boxy through the shoulders.

Open-Front Chunky Knit Cardigan

An open-front chunky cardigan is the other piece worth having by the door all season, like this open-front chunky knit cardigan from Kohl’s. Look for a relaxed, forgiving fit you can wear open over a fitted top now, and buttoned up over a turtleneck later.

Quince Organic Waxed Cotton Barn Jacket

Barn jackets are having a real moment right now, but a well-made one in a neutral, waxed cotton isn’t a trend piece, it’s a jacket you’ll still reach for years from now. The Quince organic waxed cotton barn jacket is the one I keep coming back to. Check the sleeve length before you buy, since this style tends to run long.

Choose Tops With Texture, Not Just Color

August is when I start looking past basic tees toward tops with a little more personality, a Henley neckline, a pointelle knit, a bit of embroidery. These small details do a lot of work: they make a top feel intentional rather than like an afterthought, and they transition easily from bare-legged summer days to layered fall outfits.

Lands’ End Polished Rib Henley Top

A rib-knit Henley is one of the most reliable basics you can own, the Lands’ End Polished Rib Henley Top is a good example of the style to look for. Look for one with a little stretch in the fabric so it moves with you instead of pulling across the middle. It works alone now and disappears nicely under a jacket later.

Talbots Pointelle Charming Cardigan

A pointelle-knit cardigan is worth the splurge if you find one you love, like the Talbots Pointelle Charming Cardigan. The open, delicate knit adds texture without adding heat, which makes it wearable well before it’s truly cold outside. Because pointelle knits typically have very little stretch, I’d size up if you want room to layer underneath.

Croft & Barrow Embroidered Top

An embroidered or lace-trimmed top is my go-to for dressing up jeans without looking overdressed, think along the lines of this Croft & Barrow embroidered top or the Lands’ End lace trim tank below. These tend to run true to size, but I always check whether the fabric skims or clings before I buy, a top that skims will get far more wear.

Lands’ End Lace Trim Tank

Buy the Jeans You’ll Actually Reach For

I don’t buy new jeans every August, but if a great pair crosses my path, I don’t wait either. The style I look for changes less than people think: a relaxed straight leg or a slightly loose fit with real give in the fabric wins out over anything rigid or trend-driven, because it’s comfortable enough to wear constantly, which is really the whole point.

Quince High-Rise Relaxed Straight Jeans

A relaxed straight-leg jean in a high rise is about as close to foolproof as denim gets, the Quince High-Rise Relaxed Straight Jeans are a good place to start. It doesn’t chase a trend, so it won’t look dated next season, and the fit is forgiving enough for everyday wear. If you’re between sizes, I’d size down rather than up, since this cut tends to run generous through the hip.

Gap UltraSoft ’90s Loose Dolphin-Hem Jeans

A soft, stretch-forward denim in a loose silhouette is worth having too, especially if your closet is full of stiffer, more structured jeans. The Gap UltraSoft ’90s Loose Dolphin-Hem Jeans are a great example, the comfort factor alone makes it one you’ll wear on repeat.

Don’t Overlook Shoes

Lifestride Zee Loafer

A good loafer is the one category people forget to shop for in August, and it’s the one I’d argue matters most. The LifeStride Zee Loafers check every box: polished enough for trousers but comfortable enough for jeans, and it doesn’t need a long break-in period. A little texture, like a croc print, adds interest without looking flashy, and a loafer like this will carry you from late summer straight through fall.

One Last Thing

August shopping isn’t about buying a whole new wardrobe. It’s about being selective: a good layer, a couple of textured tops, jeans that earn their keep, and shoes that work now and later. Buy those few things well, and you’ll spend a lot less time shopping come October.

What category are you shopping for first this month? I’d love to hear what’s on your list.

To GOD Goes The Glory!

Verse Of The Day

Proverbs 18:21 (NIV)
²¹ The tongue has the power of life and death,
    and those who love it will eat its fruit.