Keeping up with the latest fashion trends can be pretty overwhelming, but thankfully, one of the golden rules of classic good looks is: Simple is always better. The A-list actress above, Naomi Watts, has beautiful simplicity down and she looks expensive. But, you know what else simple usually is? Cheaper!
Autumn is on its way and one of our favorite, always stylish looks for fall is a pretty dress and some statement boots. We’ve rounded up ten of our favorite dress and boot combos perfect for all different occasions–and all under $250!
Naomi Watt’s Clean & Chic look:
Look: Work it Out
Don’t let your dreary nine-to-five schedule and paycheck-to-paycheck living get in the way of looking red-hot at work! Red is the color of confidence and the bow-accent lends a little daytime drama. These Aerosole boots might look simple, but they are amazingly comfortable and perfect if you are constantly “on your toes.”
Red bow-front dress from ASOS: $91.00
Aerosole black boots: $59.99
Total price: $150.99
Look: Dinner Party
Usually, a dinner party isn’t as formal as a regular night out, but you still have to wear something cute and make sure your shoes are comfortable enough in case you have to stand around cradling a glass of wine. The open swing of this dress keeps you from looking giant after a huge meal and these delightful little Born booties are so very Victorian glam.
Vero Moda black and ivory lace dress: $73.81
Born black booties:$149.95
Total price: $223.76
Look: Savage Shopping
We love to spend our late Saturday mornings shopping for greats deals at malls, on our favorite retail-oriented streets, and at swap meets. Shopping is almost like a sport, so dress accordingly. An animal print maxi is totally forgiving while still being stylish and these fringe Minnetonka’s are great walking shoes.
Mink Pink Into The Wild Maxi Dress: $110
Black Minnetonka boots: $90.00
Total price: $200.00
Look: Garden Party
Having tea at a garden party or for a walk through the park? This look is young, fresh, and feminine. The green weathered lace-up boots add a little bit of edge and you won’t be afraid of getting them a little dirty.
Floral burn-out from Free People:$128
Green leather lace-ups from Kensie: $79.00
Total Price: $207.00
Look: Sunday Brunch
Meeting your friends for an early morning brunch, but don’t have the energy to think about your outfit? This brown striped maxi and brown cowboy booties are an ideal way of looking cute while virtually being in your nightdress.
Max & Mia brown stripe maxi dress: $88.00
Brown woven cowboy boots from Forever 21: $36.80
Total price: $124.80
Look: Cocktail Hour
Going for first date drinks after work? This black wrap dress is sexy while still staying modest and these playful cream booties add a little bit of edge to show that you are fun, but shouldn’t be “messed with.”
Another perk? The heels on the booties are really low, so they add height, but not so much height that your heels plus a couple of glasses of vino will send you face first into some bushes.
Faux wrap dress from Banana Republic: $94.00
Edgy cream Naughty Monkey booties:$56.00
Total Price: $250.00
Look: Getting Classy
Looking for the perfect understated day-to-day look for class? This denim dress can be mixed and matched with so many accessories and these brown boots are super cool, but very practical. This smart combo is a total A+.
Denim dress with belt from Forever 21: $24.90
Rumplestiltz brown boots: $89.99
Total Price: $114.89
Look: Black & White
For us, this look is perfect for anything: work, a date, going to class, going to a show. It’s a perfect mix of sweet and sexy with a funky pattern and edgy lace-ups on the boots.
Missoni for Target Space-Dye knit shirtdress: $54.99
Kelsi Dagger bootie wedge: $195
Total Price: $249.95
Look: Late-Night Library Sesh
A super cozy cable knit sweater for those chilly nights in the library and some totally walkable leather booties with ruffle details and leopard print. So cute!
Cable-knit sweater dress from H&M: $69.95
Cognac leather booties with leopard print detailing by Betsey Johnson: $129.95
Total price: $199.99
Look: Third Date
Ahh, that special third date where women around the world decide if they are going to go to, ahem, third base with their date. You want to look cute and classy, but add a little sex appeal to get the process going.
That’s why this high-necked, girlie, but short dress looks innocently hot with these knee-high wedge boots.
Rare butterfly flocked dress: $71.35
Dolce Vita Torino boot: $125.99
Total Price: $161. 34