The Best Transitional Looks for Back-to-School Season and Beyond

Date: August 30, 2024

If you’re a parent, back-to-school season is probably somewhat of a holiday in your home. (Hey, we totally get it!) You’re busy getting the kids ready for another year of activities and adventures, which means lots of shopping—for them and for you! Even if you don’t have kids, there’s no better time to refresh your wardrobe and change things up than the beginning of September. Just pretend you’re a grown-up kid getting some new school clothes and creating back-to-school outfits!

A woman poses in a plaid jacket over a grey hoodie, combined with black wide-leg jeans and red flats, offering a polished and trendy back-to-school outfit. The mix of patterns and textures adds visual interest, making it a standout look for cooler school days.

The first few weeks of September are the perfect time to transition your favorite summer pieces to fall. You don’t have to give up on cutoffs and sundresses entirely; just get creative and strategic with your layering or swap sandals for sneakers, boots, or loafers to “autumn-ize” your looks.

What to wear for school activities (or the office)

Remember how you were so excited to wear your new clothes on the first day of school, no matter what the temperature was? Extend that feeling to today! Maybe you’re a teacher, or perhaps you’re heading to school to get your kids situated or to work an event. Whatever the occasion, there’s no harm in getting a little glammed up. This rule also applies to a day at the office; why not turn up the volume for a Monday morning and have a little fun?

A woman stands elegantly in a sleeveless brown top and high-waisted wide-leg jeans, showcasing a chic back-to-school outfit that balances comfort with sophistication. The relaxed fit and earthy tones make this outfit versatile for various occasions throughout the school day.

A denim or T-shirt dress feels low-key but still looks like you tried, as does an effortlessly cool jumpsuit. Wear your favorite summer slip dress or sundress with a “third piece” like a denim, cargo, or leather jacket or layer a button-down shirt over it for extra coverage—a cool and easy way to take the summer dress in a fall-forward direction.

What to wear for football and soccer games

Comfort and ease are key here. Flat shoes are your best bet since they won’t sink into the grass, and layers make life easier as the temp starts to drop when the sun goes down. In the early weeks of back-to-school season when it’s still fairly warm outside, try an easy midi tank dress and layer with a denim or cargo jacket or stick with your go-to cutoff shorts and throw a lightweight knit sweater over your tee or tank. Toss a blanket, hat, and sunglasses in your tote bag and don’t forget the snacks!

What to wear for weekend errands

Keep your cutoffs in rotation until it’s too cold! They’re a surprisingly versatile transitional piece, and we’d argue that they look just as good with a sweater as they do with a vintage-inspired T-shirt. A pair of shorts with a loose-fitting knit or half-zip and some sneakers always looks cool but still easy and casual, and provides lots of styling space for accessories too.

First Image: A woman wearing a vibrant red pullover paired with distressed denim shorts, creating a stylish and casual back-to-school outfit perfect for warmer days. The bold color adds a pop of energy, making it an ideal choice for a laid-back, yet confident look.

The weekend is the perfect time to incorporate one of our favorite fall styling trends: the pop of red. Add a touch of bright crimson with a baseball cap, sneakers, flats, or a cross-body bag. Bright red accessories take even your most basic weekend looks to the next level by adding visual interest and cheerful color. If we could give you a fall dressing report card, you’d definitely get an A+.