How Sydney Wears It: Dressing for Milestone Moments

Look your best with an outfit as major as the occasion you’re dressing for.

A few readers (hi! and thanks for your e-mails!) wrote in with questions about what to wear for a really big-deal moment in their lives, so I thought I’d try my hand at styling a few looks for the occasions. With the help of my editors, I sourced a few samples from Ann Taylor and Jack Wills’s beautiful spring collections to pull off the looks. Locations in Georgetown (Jack Wills is located at 1079 Wisconsin Avenue, Northwest) and all over Washington (click here for area Ann Taylor stores) make these two shops surprisingly great resources for big-deal outfit components you’ll be able to wear over and over.

1) First Year of College

Q: I just started college, and I want to start moving away from my high school style toward something more sophisticated. I know that may mean more heels, but obviously I can’t wear those when I’m walking around campus all day. What would you suggest to get a new, more grown-up wardrobe started?

A: When the mood strikes, I’m a big fan of the prepster-collegiate look for a little old-school sophistication. It’s easy to pull off with only a few staples that can be mixed and matched. A neutral cardigan, a boyfriend blazer, fitted trousers, a pullover sweater, and some unlaced oxfords are all great starter pieces for moving your wardrobe in the more sophisticated direction. To keep your look from appearing too stuffy, consider adding a bright statement necklace.

 Jack Wills Hollingworth skinny chinos, Glenthorne brogues (worn unlaced), Sancomb cable-knit sweater, and chambray Denholm shirt, Ann Taylor Supernova statement necklace (available March 6)

2) First Full-Time Job

Q: I’m a recent college graduate and just landed my first job at a PR firm. What would you suggest wearing to the office that will look grown-up and not college-like (if you know what I mean) but not boring at the same time?

A: First of all, congrats! My advice would be to steer clear of the pantsuit. On occasion they can look beautiful, but most of the time they veer toward boring. I would recommend stocking your wardrobe with a few classic pieces like a black coat or blazer, (even better if they have interesting leather detailing!), a few beautiful pumps, and sophisticated jewelry. To spice up the look a bit, try pattern mixing with an animal-print skirt and a thin-stripe top or blouse. If a whole skirt is too much animal print for you, try a more subtle animal-print skinny belt instead.

Aldo Shoes (similar), Target skirt (similar), Ann Taylor jewel neck striped top and Modernist Coat, Urban Outfitters glasses (similar), Gold Watch (similar)


3) First Black-Tie Event

Q: I’m going to be attending my first black-tie event with my boyfriend, but I’m kind of stuck about what to wear. Honestly, I find typical evening dresses to be kind of boring. Is there a way to look trendy and formal at the same time? Help!

A: Yes! Wearing ballerina-esque skirts has been a favorite look of mine for a while (see here and here for more inspiration!), and this trend would work beautifully for a black-tie event. Keep your silhouette simple and sophisticated with a waist-emphasizing skinny belt, a neutral cardigan, and minimalist jewelry. Bonus points for a fun pairing of neon and neutral.

Ann Taylor tulle ballet skirt (online exclusive), Target sweater (similar), J. Crew belt, Ann Taylor Neon Lights necklace and bracelet (available Feb. 21)