Q: I’m going through a style change and need some guidance. I used to wear a lot of dresses, but now I am leaning toward changing my personal style. I’m thinking of something similar to Ellen DeGeneres’ look. I love the blazers, slim pants and oxfords. Can you recommend some places to shop that sell androgynous staples? Do you know of any sites or bloggers I can view to get more ideas for this style — and hopefully make my own look?

A: I’ve made some significant changes in my own personal style recently, so I know how exciting the process can be. I hope you’re having a blast as you switch up your look. In terms of where to shop, Everlane is a great resource for androgynous basics such as tees, simple sweaters, minimalist slacks and button-front shirts. (Bonus: All the wares are sustainably made.) Wildfang is a brand that bills itself as tomboy-centric, offering everything from trendy joggers to sleek suiting. And for timeless classics in a variety of sizes (including petite, tall, plus and petite plus), try Lands’ End.

In terms of recommended reading, start with the website She’s a Gent. The outfits the blogger assembles are breathtaking in their attention to detail, from elegant pocket squares to meticulous print mixes. A Tumblr blog called She Does Him Fashion runs a close second, and the founder is a wizard with layers. La Garçonnière focuses mainly on suiting, but the site’s mastermind has impeccable style and mixes her decidedly menswear-ish clothes with more traditionally feminine shoes and finishing touches. Finally, peek at Qwear for brand reviews and style profiles.

Q: I am 55 and work at a high school with students in a fairly visible role. Thankfully, I can wear casual clothes — jeans, khakis, etc. Where I struggle is in choosing shoes that I can wear with straight or skinny jeans and still be comfortable. In warm weather, I have lots of options. But I have no idea what to wear when it’s cold. What kind of shoes do you recommend with jeans and casual pants that are fun and comfortable but can be worn with socks?

A: Ankle boots for the win! They come in a mind-blowing variety of styles and heel heights, which means they can accommodate the gamut of comfort and aesthetic preferences. Skinny jeans can be tucked into ankle boots with higher shafts. But go ahead and wear straight legs untucked over the boot top — so long as you pick a style that sits fairly close to your ankle. (Ankle boots that are slim in the shaft are generally more flattering and versatile.) Plus these boots are marvelously sock-friendly. Pick a pair in your favorite neutral, and get them into your cold-weather classroom outfit rotation.


Q: I’m an office assistant and a mother of two. And because of those two, I look permanently pregnant when I sit down. Regular pants make it worse, and I don’t even bother with pencil skirts. Plus, with our winters dipping to 40-below, dresses and skirts aren’t really advisable for bus travel. It’s not much of a problem when I’m hidden behind a desk all day, but it’s a little disconcerting in other circumstances (such as meeting with the boss, say). Any suggestions?

A: Dressing for a post-pregnancy midsection is challenging for many women. It’s completely natural and normal for your figure to shift its shape with the arrival of a baby, and yet those physical changes can take their toll on a woman’s confidence. Here are a few tricks to try.

• A soft but structured jacket is a solid bet for anyone hoping to add shape to or downplay her midsection. Drapey cardigans will only add volume, but blazers and jackets have enough built-in rigidity to streamline your silhouette. Skip superstiff wools and twills. Think heavy knits and ponte.

• Some women opt for shapewear to keep their midsections in check, but wearing shapewear every day is neither comfortable nor healthy. Adding a snug but stretchy camisole, on the other hand, may help reshape your abdomen a bit without squeezing your organs. A nylon/spandex tank that’s nude to your skin tone will slip invisibly under virtually any layer.

• If you are comfortable only in loose, flowy tops, balance them out with slim-fitting bottoms. In fact, the “long over lean” formula of a midthigh tunic worn with leggings or skinny pants can create great proportions.


Sally McGraw is the author of Already Pretty, a daily blog about the intersection of style and body image.