Welcome to what is probably our final “next step” feature, where we explore how to take the next step up in work clothes, office heels, stylish work bags, and professional jewelry; we also explored the middle upgrades for services (e.g., you can cook for yourself or get a professional chef — but what’s in between?). Today: how to step up your weekend clothes game. (Pictured: Vince Gathered Shirtdress, on sale from $385 to $230 at Nordstrom.)

Here is my theory on weekend clothes: there are very few classics. At the rate that fashion moves these days, the quickest way to look and feel frumpy is to have an outdated off-duty style. I speak from experience here: I refused to buy in to the skinny jean trend for <cough> way too long, arguing that bootcuts were classics and fit right in to the style for weekend me. So what if I’m still in bootcuts when everyone else in skinny jeans, you may say — it’s just denim, and I’m in suits or sheath dresses five days a week. But I’ve noticed that a lot of elements of your workwear wardrobe can flow from weekend choices.

For example: a fitted t-shirt looks great with bootcuts, but you need a drapey, tunic-y, asymmetrical top for skinny jeans. The slouchy, more boxy tees and sweaters (or, gah, the crop tops) look better with boyfriend jeans. Once you get used to doing the half-tuck with your jeans on the weekend, your office style changes as well — to more drapey blouses with slimmer-cut pants. Similarly, once you get used to rolling your jeans to wear with your booties, wearing knee-high boots with skinny jeans feels almost antiquated — which means you buy fewer knee-high boots or don’t replace the ones you have, and then it’s less of an issue whether it’s appropriate to wear knee-high boots to work with dresses, and instead we start talking about whether booties with skirts are work-appropriate. It’s very interesting to me how all of the pieces interact.

This is all just a theory, and I’m curious to hear what you guys think about it. I’m still perfecting my own weekend game, but I think this is where the capsule collection really comes in — you buy a few of-the-moment pieces that all work together in terms of color, silhouette, and vibe, and try to keep your new purchases to a minimum. I also think that if dresses work for you in your off-duty life, they’re one of the best ways to stay as close to “classic” as you can get.

Anyway, here are my tiers for weekend wear — readers, where do you shop for weekend clothes? Do you also feel like casual fashion is moving far more quickly than it has in the past — and how do you address it? Or, is all of this less of an issue because you’re either in a suit, workout clothes/sweatpants, or a date night slinky dress, with very little in between time?  

Tier 1 — These stores are easily accessible, and you probably shopped at them in your teens. The pros: they’re affordable and always on trend. The cons: a lot of their cuts and trends may skew a bit younger than you prefer; the clothes are not made to last (generally speaking); and you may want to consider the ethics of buying a ton of “disposable” clothes.

• American Apparel
• AE/American Eagle
• Express
• Gap
• Forever 21
• H&M
• Loft
• Old Navy
• Ruche
• Uniqlo
• Urban Outfitters
• Specific brands:
  • Aqua (at Bloomingdale’s)
  • Halogen (at Nordstrom)

[Read more…]