Your Biggest Fall Fashion Questions Answered by Our Resident Style Expert

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From boots that fit wide calves to suits that are anything but boring, our in-house stylist has solutions for all your seasonal wardrobe issues

Whether you're actually going back to school, heading into an office or filling up your social calendar, fall presents an opportunity to begin a new sartorial journey. It's time to store your summer dresses and sandals and shop for a few key seasonal pieces

Shopping for fall clothes and accessories (or anything really)  is always exciting, and weather that permits more layering opens up a world of possibilities. But with all those options also comes indecision and online shopping paralysis (we know it well!).

If you’re looking for some guidance, you’ve come to the right place! Our resident fashion expert and in-house stylist answers the season's toughest style questions with quality, wearability and price in mind. From no-gape shirting to tall boots for wide calves and other popular, yet specific, Qs, we’re guiding you along a fail-proof journey of the season’s top eight essentials.

Q: Where can I find a black blazer that's not too slim and not too boxy?


The Frankie Shop Oversized Blazer, $165;
The Frankie Shop makes top notch blazers for fashion girls, including this one-size-fits all boyfriend style which magically fits a wide range of shapes and sizes. The result is an effortless, French-girl-chic silhouette that doesn't feel like it's straight out of the 80s.

Good American Fitted Blazer, $169;
With strong bold shoulders and a slimming effect at the waist, this Good American blazer means business. It comes in a wide range of sizes and is made to show off your curves without being overly boxy. Consider this the Kris Jenner uniform that's sexy, sophisticated, and ultra flattering.

Zara Basic Blazer, $90;
If you're looking for the perfect middle ground blazer that touches upon the boxy 80s fit, boyfriend style, and slim waist, look no further. This has strong shoulders for a fashion statement without feeling costume-y. The body slightly tapers giving a feminine shape with plenty of room to move. It’s great with denim, skirts, or even over a zip up hoodie and leggings for an athleisure, pilates-to-brunch moment. Plus, it's under $100!

Q: Where can I find a luxe-looking work tote for under-$200?


Mark + Graham Leather Tie Tote, $130;
This classic carryall tote is designed with a bow tie detail and key chain hook. It’s simple, giving you exactly what you need for seasons to come. Plus, in true Mark + Graham fashion, it can be monogrammed for personalization you’ll have forever.

Leatherology Uptown Vertical Tote, $185;
Leatherology makes high quality leather at an accessible price point. It’s a low profile, slim option that fits nicely under the shoulder without feeling too bulky.

Calpak Haven Laptop Bag, $178;
This bag is minimal in design on the outside, but has a ton of secret compartments on the inside to delight the ultra-organized. From a laptop sleeve to key hooks, interior and exterior pockets along with durable straps, this bag doesn't miss a trick and is a great go-to for travel.

Q: Where can I find a "cool" suit for a conservative workplace?


Mango Pinstripe Blazer, $129, Pinstripe Vest, $60, and Chalk Striped Pants, $80; 
Three-piece suits are having a moment right now, and lighter colors are particularly "in" — though the pinstripe keeps it all-business. Plus, the fit can be dressed up for the courtroom with pumps or down for a casual Friday with classic white sneakers. You can even divide it up and wear each piece as separates.

Aritzia Artusi Vest $118 and Windmill Pleated Skirt, $150;
Who said suits have to be trousers and a blazer?! This set from Aritzia is a fresh take on the classic skirt suit. The pleats are sophisticated and conservative while the vest top is modern and cool. Layer a black blazer over it or style a white button down shirt underneath for a preppy vibe.

M.M. LaFleur The O’hara Blazer, $395 and the Mija Pants, $265
The blazer has a boxy cut balanced out by slim shoulders, making it a flattering fit for all. The wool fabric is stretchy but structured, wrinkle-resistant and machine washable—making it the easiest, most investment-worthy two piece suit that's Park Ave.-approved and downtown cool.

Q: Where can I find tall boots for athletic calves?


Vince Camuto Sangeti Wide Calf Boots, $229,
These boots were made for walking! Reviewers rave about how comfortable they are with just the right lift in the heel. The square-ish toe and flared block heel give a classic silhouette a modern update. It’s giving attitude and sass and ready to strut!

Madewell The Antoine Tall Boots, $298;
These are a take on a western style boot that feels fresh, elevated and cool. The style comes in regular and wide-calf fit. The small heel stack gives a little lift and sophistication without taking the high heel route. All that means comfort for days!

Naturalizer Gen N Wide Leg Boots, $200
Before you run away from the three inch heel, know that these boots are designed with orthopedic comfort in mind, like all of Naturalizer's styles.The leather is soft and flexible while the footbed is contoured for all day wearability.  Plus, the chocolate brown leather feels super luxe, so no one will ever know it’s a comfort shoe.

Q: Where can I find an affordable cashmere sweater that doesn't pill after a few wears?


Italic Mila Cashmere Boxy Crop Sweater, $165;
If you’re unfamiliar with Italic, you're about to wonder what took you so long to find them. The brand prides themselves on luxuriously-made products without the high price point of a name brand. They are transparent about how their products compare to luxury names and draw attention to their quality construction. This sweater is a perfect example: 100% cashmere and with a weave gauge of seven, for under $200.

Boden Eva Cashmere Cardigan, $175;
Cardigans are hot right now! It’s perfect for transitional weather and can be worn many different ways: Layered over a crisp tee, buttoned up on its own, or unbuttoned to show a lacy camisole for a sexier approach. It’s perfect for transitional weather and can be worn many different ways.

Nadaam The Essential Cashmere Sweater, $75;
This sweater is lightweight and soft but not the least bit sheer. It's the perfect transition top that will keep you warm and cozy without feeling heavy. And for under $100, you might want to snag it in a few colors.

Q: Where can I find statement earrings that won't weight down my earlobes?


Baublebar Stephanie 18K Gold Earrings, $72;
These dangly earrings can be dressed up for weddings or down with denim. They might look heavy but they only weigh .08 oz.

Marin Costello Ven Hoops, $88;
The thin double hoop design brings all that big hoop energy without overpowering your ear lobes or adding uncomfortable heft.

Anthropologie Linear Pearl Drop Earrings, $48;
Pearls aren't typically associated with statement earrings, but this modern and edgy style makes a big impact and is lobe-friendly.

Q: Where can I find a button down that doesn't gape at the boobs?


The Shirt Icon, $108;
The Shirt lives up to its straightforward name: It's all about the perfect white button down. This one is  made with a “no gape” button technology that reinforces the spot where one typically finds an annoying opening. The particular style has over 200 five-star reviews from customers that won't wear anything else. 

PerfectDD The Classic Button Down, $225;
Women’s bodies come in all different sizes, not just small, medium and large. So it can be frustrating trying to find a simple button down shirt that fits. PerfectDD makes clothes specifically for larger busts. This style has added fabric in the chest to ensure zero gaping.

Lands End No Gape Long Sleeve Stretch Shirt, $50; landsend,com
Lands End figured out a solution to this problem years ago and have truly perfected it. For a $50 price point, you can score a “no gape” hidden-button feature that prevents any openings at the bust. The stretchy fabric is comfortable and functional while the sheen feels fresh with every wash.

Q: Where can I find a new fall jacket that isn't denim and won't go out of style?

Sezane Scott Trench Coat, $305;
Trench coats never go out of style and this version from Sezane delivers French girl chic in a goes-with-everything khaki hue.

Free People Highlands Solid Peacoat, $168
This cropped version of a peacoat is a modern take on the season's most popular topper. Its oversize fit is also great for layering over sweaters when it's chilly out.

Gap Utility Jacket, $80;
The army jacket has the same versatility as a denim jacket but it feels a bit fresher and more elevated for fall. This style from Gap has a drawcord at the waist so you can cinch it to balance the proportions of your fit.

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