It’s that time of year again. The all-too-familiar September into October style struggle. The “Can I still wear this? Will I be too hot or too cold?” internal monologue we have with ourselves whilst peering into our closets each morning.

If you can’t tell, I have a bit of a love/hate relationship with these bipolar weather weeks. I’m not one to wish the hot weather away, but like any true Minnesotan, I live for the change in seasons. I wish I could say it was because of the foliage, or because of the fun fall activities that come along with the temperature drop (apple picking, anyone?). Truthfully, I just can’t wait to welcome fall fashion with open arms.

Let’s face it, dressing for these in-between days can be dumbfounding. Some days are just too damn hot to wear anything other than sandals and cut off jorts; others you’re reaching for that chunky sweater tucked deep inside the bowels of your closet. But if you ask me, there’s also something fun about these short-lived temperatures: they allow for interesting layering and outfits comprised of both your summer staples and those fall pieces you’ve been counting down the days to bust out.

Instead of going rogue and investing in all of the new fall pieces I have in my various online shopping carts, I try to get creative and push myself to think outside of my traditional wardrobe box. Ahead, you’ll see some of the summer-to-fall transitional looks I’ve rounded up to help you get more mileage out of your summer staples.

Style Tip No. 1: Warm Weather Soles

Don’t be afraid to stretch out sandal season. I know it can be hard to contain the excitement for booties and loafers of all kinds, but come winter (when your toes can’t see the light of day without catching frostbite), you’ll thank yourself. I love the juxtaposition of a strappy sandal and a chunky knit. A great trench coat will extend the life of your wedge espadrilles. All about that comfort game? IMO, white sneakers are to be rocked all year long. Try adding some knitwear with yours, like a cozy pair of socks or a sweater dress.

Women’s Madewell Tie Cuff Pullover Sweater • Madewell • $79.50
Women’s Adidas ‘Stan Smith’ Sneaker • adidas • $60
Women’s Topshop Editor’s Double Breasted Trench Coat • Topshop • $150
Antipast Women’s Striped Mid-Calf Socks • Antipast • $40
Reebok Melted Metals sneakers • Reebok • $99.39

Style Tip No. 2 Summer Denim

To hell with “the rules.” Of course, you can wear light denim after Labor Day. This fall, color is the new black. Try out a bright 70s-inspired striped sweater to instantly turn your white jeans autumn-appropriate. Or, pair your acid washed, cropped jeans with some booties to fill in the ankle gap. And there’s no need to retire your denim minis just yet. However, you’ll want to swap out your favorite off-the-shoulder blouse to avoid looking too summery. Instead, try for a transitional topper, like a bell-sleeved knit or oversized blazer (I’m currently loving all things plaid).

Scripted Striped Bell Sleeve Sweater • $49.50
Women’s Madewell 9-Inch High-Rise Skinny Jeans • Madewell • $125
Women’s Free People Velvet Trim Blazer • Free People • $168
Ash Feel Booties • Ash • $250
Women’s Madewell Retro Ripped Knee Crop Bootcut Jeans • Madewell • $128

Style Tip No. 3: Lightweight Dresses

Does the thought of retiring all of the summer wedding-guest dresses you bought give you (and your bank account) major anxiety? Repurpose them by upping your layering game. I’m a big fan of the slip dress and cardigan combo. Your patterned sundresses can be worn well into fall as you wear it with heavier materials, like leather or suede. Been slacking on the self-tanner front? (I’m guilty as charged) It’s not too early to whip out a pair of tights and lace-up ankle boots to pair with a mini dress.

Emerson Thorpe Hallie Slip Dress • $195–325
Women’s Madewell Kent Cardigan Sweater • Madewell • $98
Dune London PEBBLE – BERRY Block Heel Velvet Ankle Boot • Dune London • $80–96
H&M Patterned Dress • H&M • $69.99
H&M Biker Jacket • H&M • $69.99

Elevate your transitional looks with some of my fall picks

Joie Jemora B Frayed Plaid Blazer • Joie • $398
Levi’s 501 Skinny Jeans • Levi’s • $98
Topshop Moto corset detail denim skirt • Topshop • $60
Henschel New Shape Ivy 4511 Newsboy Cap • $42.95
Loeffler Randall Carter Low Heel Ankle Booties • Loeffler Randall • $395
Mansur Gavriel – Suede Ankle Boots – Chocolate • Mansur Gavriel • $595
Tularosa x REVOLVE Robbins Sweater in Red. – size L (also in M,S,XS,XXS) • Tularosa • $158
Opening Ceremony Shayenne Suede Harness Ankle Booties • Opening Ceremony • $450
Rachel Comey Oversized Trench Coat • Rachel Comey • $760

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