The Next Step: Upgrading Weekend Clothes

How to Upgrade Your Weekend Clothes | CorporetteWelcome to what is probably our final “next step” feature, where we explore how to take the next step up in work clothesoffice 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 At the rate that fashion moves these days, the quickest way to look and feel frumpy is to have an outdated off-duty style.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.

Tier 2 — At these stores the quality is a bit better, and you’re probably already shopping at many of them for your workweek look. If I were looking for a cute weekend dress, a date night top, or a pair of shorts, I’d probably hit these stores first. We also start to get into the idea of “better” t-shirts than what you find at your normal mall stores.

Tier 3 — These stores and brands feel like a bit more of a splurge to me: you have to really like what you’re buying since odds are most of it is too casual to be worn to work. Still: for that amazing dress or that perfect leather moto jacket, these are the stores and brands I’d check first.

Tier 4 — Money is no object…

Which brands and stores are your favorite for weekend garb, ladies? 


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  1. Anonymous :

    For weekend wear my big transition has been buying only at the start of the season for full price. I don’t need lots of weekend clothes, I don’t mind re wearing something I love all the time. I only buy weekend clothes on sale if I actually need something- the fun things need to be things I just loved immediately.

    • Anonymous :

      I agree with this approach! Buy a few things at the beginning of the season and then wear the heck out of them!

    • I recently started doing this too. It helps that I know exactly what I have and what I want to add and I don’t shy away from repeating outfits. Eventually, the cost per wear adjusted to the joy the item brings me makes the math right.

  2. Wait, knee-high boots with skinny jeans are out? Then how come I was seeing them everywhere I went until the weather warmed up a couple of months ago? Do I just live in frump-ville?

    • Upgrading :

      I’m sure they’ll be like Juicy velour tracksuits. Someone will always be wearing them.

      I don’t dislike them, but I think you have to do you (and me in that combo was like me pretending to be a pirate / the 4th musketeer / too costumey). I do love flat boots with dresses and skirts for weekends (but the OTK boots — no thank you).

    • Kat, I so agree!!! YAY!!!!I guess I am kind of happy that the skinny jean’s are NOT the rage this year b/c my tuchus simply PRECLUDE’S me weareing my skinny jean’s this summer! I have started to wear summer sun dresses b/c they are alot more forgiveing for girls like me who’s “shelf’ makes skinny jean’s a cheep execuse for men to whistel and tell me all of the thing’s they want to do to my tuchus. FOOEY on that.

    • Definitely everyone in D.C. was wearing that as recently as the most recent cold weather.

      • DC here and I disagree- there were remnants but knee high boots are out- ankle boots are in.

        • Hurray — I guess I’m trendy by default. I could not find a pair of knee-high boots that looked right on my petite frame, so I opted for ankle boots.

          But honestly. I do like both looks, although the knee-high look could look quite equestrian depending on the boot.

          • I think the flat riding boot is still okay-ish if worn with the right pants/jeans and a chunky, loose sweater in the right weather. It might not be anything to write home about, but when it’s very cold out, I think reason trumps trendy cute ankle booties. What’s definitely past its prime is the heeled boots and skinny jeans/pants look.

        • Be that as it may, as of last spring, they were still what you saw on the street. Which may not mean they’re trendy but they do still seem to be what most people wear.

        • What’s in, maybe, but as of the last cold-ish weather, if you hung out in a public place, you could see most of the women wearing flat, knee-high boots.

          I mean, nobody has ever accused D.C. of being trendy, but . . . .

          • I am disagreeing- I think it was only 30-40% still in knee high boots.

          • Maybe, but of the others, you have the normal percentage (at least another 30-40%) in sneakers or crocs – again, nobody ever accused D.C. of being trendy.

          • WorkingMom123 :

            I live in DC and I concur that a lot of people are wearing knee high boots. They are not out here, or at least they weren’t this past winter. I usually notice when things are “out” and I haven’t noticed an abandonment of tall riding boots.

  3. Upgrading :

    Upgrading the casual wardrobe has already happened:

    OUT: free t-shirts with words on them; things with visible paint
    IN: anything from LE and a few DVF Reina dresses from e-bay; lots of Athleta (of the ath-leisure variety)

    • Your ‘out’ list just described my entire casual wardrobe. I read it to my husband and now he’s laughing too. He also strongly feels these should be on my ‘out’ list as well.

  4. Shopaholic :

    I think it’s worth it to buy a few nicer pieces for the weekend. I was sick and tired of feeling like I couldn’t put together a decent outfit in the winter so I splurged on a few things – leather leggings for a night out, some Vince sweaters and cute booties. So much easier to get dressed and feel put together. It’s only 2 days a week but who wants to look like a frump 2/7 days?

    For the summer though, I tend to wear a lot of sundresses or maxi dresses and I already had some from last year so I’m just rotating through a few.

  5. I think Tier 2 should really be two different tiers, or at least 2A and 2B. In terms of quality, price and even ethics there is a world of difference between, say, Nanette Lepore and Banana Republic/Ann Taylor. I’d also move Uniqlo into the first tier 2 because quality wise it’s actually a lot above much of BR or JCrew/JCrew Factory.

    That aside, although I agree with Kat that you have to pay attention to the subtleties, I think there are “classic” weekend looks. Jeans and a t-shirt will always be classic, you just have to pay attention to the details. I’m not sure it’s that much different from suits or work dresses, where the lapels, lengths, shoulders, etc., change from time to time.

    I’d also throw in that, for me at least, the difference between cute and frumpy often boils down to accessories. I could wear the most of the moment whatever and pair that with some havaianas and suddenly the whole thing isn’t so cute. I’d love to see a round up of weekend accessories – anything from cute keds to cross body bags in fun colors.

    • Agree with AIMS on tier 2 being too broad.

      My problem with weekend clothes is that casual wear tends to be more trendy than work wear. If what’s current is not my style, I feel like there’s nothing available for me. I want a few summer casual dresses, and could use some lightweight casual pants, but I’m not finding anything that I would wear. I’ve tried on a few things that I thought weren’t me, and only confirmed my suspicions. (When did Hammer pants come back???)

      • BeenThatGuy :

        That printed pajama/Hammer pant look is adorable…but not for me. I have only seen a few people pull off that look well. I have officially stopped looking for summer clothes and am rotating my things from last summer. I can’t seem to find anything I like either.

        • Meg Murry :

          I fear I have now crossed that threshold where all the trends are “things I wore once in my youth and just can’t bring myself to go there again.” I might be able to get back on the flannel and doc martin train if that comes back around (or did I miss it already?) or tiny touches like a few bright neon accents, but I just can’t do full out trendy again.

          Bah, I feel so old. Get off my lawn, put on some clothes that cover your body and pull up your pants. Kids these days! That’s it, I am turning into a combo of my grandmother and high school principal!

          • Thinking of SF :

            Yep. This is why I can’t do maxi dresses and jean jackets. Got burned out on this in the 90s.

          • BeenThatGuy :

            This. And yes, the Doc Martin train has come again (and gone, I think). Huge in the toddler fashion community. OMG, did I really just type that?

  6. Meg Murry :

    Caveat: I’m not trendy at all, I live in rural Midwest so it takes a while for me to see a lot the trends filter to me, and I have 2 kids and a job where I can dress jeans casual most days, and can find clothes that are “client is coming to the office” appropriate in Tiers 1 and 2.

    Therefore: A big chunk of my clothes come from Tier 0.5 – Target. Most of my “nicer” weekend stuff comes from Tier 1 stores (both those listed, and a few that aren’t, like Lands End and some of the Macy’s house brands). I have a very small but growing handful of Tier 2 and 3 clothing items that I’ve purchased at resale shops or TJMaxx/Marshalls, and I’m slowly growing those with things that are at least “a few years usable” timeless, since I know nothing is truly timeless (or will fit my shifting shape forever).

    Since I work in a job where getting messy and ruining clothes is always a possibility, I just can’t afford to ever really splurge. I work in a lab, and most days I know when I’m going to be doing lab work and dress accordingly, but the days when I wear my nice stuff and “just run in to the lab for a minute” are the days when disasters happen. And when I say ruin, I mean ruin – I work with materials that if I’m a little sloppy about they will at best leave me spattered and at worst stain the entire item or clothing or eat holes in the clothing, and there are all kinds of sharp edges I’ve ripped clothes on.

    For a long time, my weekend clothes and work clothes just blurred together, because they were almost all at the jeans casual level. I’ve found that I feel a lot better though if I set aside a handful of favorite items that do NOT go in to work – one pair of well fitting jeans that aren’t faded or worn in spots, a pair of black pants that are still actually black and fit well, a couple of nicer sweaters (those can theoretically go to work and get left in my office, but I try not to very often) and nicer tops that I feel good in, a few summery comfy dresses, etc. Then I have 3 tiers of clothes – nice looking work clothes, decent looking (and fitting) weekend clothes, and slightly scrubby work clothes for dirty work days – with some of the scrubby work clothes coming from demoted weekend wear.

    Do people actually buy some of the Tier 3 and 4 items for weekend wear? I’m sure people do, but no one that I regularly interact with in my real life. May I ask, what kind of occasions are you wearing these items for? My evenings and weekends generally consist of running errands and chasing kids, and as I mentioned above, my look is generally more on the “trying not to be too frumpy” as opposed to the “trying to be perfectly on trend” end of things. Or maybe I just really don’t notice these things, and the Tier 3 and 4 wearers just fall into that undefinable “look effortlessly well put together” unicorn category.

    • Anonymous :

      I have a piece or two of tier 3 for fancy brunches, bridal showers, day dates etc. not much but I do wear it.

    • I’ll bite! I just bought some tier 3 items for weekend wear. I’m childless and live in an urban area, both of which make this decision practical. Last weekend I wore a tier-3 dress to a play and a tier-2b dress to walk around at a local festival. Most of my weekend wear is lower than tier 3 but I look better when I sprinkle my wardrobe with high end pieces (expensive denim, I’m looking at you).

    • West Coast :

      I would say about 50% of my weekend wear is from the tier 3 category, with the rest being 35% tier 2 and 15% tier 1.

      The pieces I tend to buy are jeans, shorts, khakis, skirts, nicer tops and jackets. The recent exceptions were tank tops and a long sleeve shirt (looked at tier 3, but could not find the fit / colors I wanted), and a vintage Gap utility jacket. I am a stickler for quality and the ‘feel’ of clothes, which is what drives me to tier 3. I wouldn’t say that I am focus on trend, but do try to buy a new pair of AG jeans once or twice a year to stay current.

      I wear the tier 3 clothes to the beach, to brunch, to wine tasting, on outdoor adventures, out at night, dates, on errands. The nicer tops are generally reserved for some of the brunches, wine tasting, going out because they are dry clean only.

      If I do have an event were I need a nice dress, it will also usually come out of the tier 3 category.

    • Pretty Primadonna :

      I preface this by saying I am a clothes horse:

      I have some Tier 3 clothes, mostly dresses, for sorority and Junior League events, date nights, and the like.

      In terms of running around clothes for the weekend, I have been intentionally purchasing nicer quality, less “disposable” clothes. So, for instance, Tier 2 sundresses instead of Tier 1. I associate Tier 1 stuff with the juniors department and can tell the difference in quality, particularly material. I want easy, throw-on dresses for summer. However, when the material is so thin it is transparent, it becomes an issue to find the proper undergarments, wear a slip, etc. Plus, I just think I am of an age that I need to step my game up in terms of how I present myself whether at work or at the grocery store on Saturday morning.

    • Are you my long lost twin? You wrote exactly what I was going to write. I’m just a little different in that my work wear has to look professional and I’m never in jeans for work but for weekends, it’s Target all the way. I’m running around doing errands, taking care of my kids and cleaning the house. I don’t really need anything beyond the 0.5 or 1 Tier. Most of my friends are the same way. I guess if I had friends who did wear Tier 2+ then I might be pressured to do the same but I don’t.

    • Kudos for Tier 0.5. But my social life is minimal…

  7. I would argue that this list is woefully inadequate if you aren’t a standard size.

    I’m a Tall, often an XL, and I can’t shop well more than half of these brands.

    Also, I’m a Californian, and even though I live in Boston, I hate boots. I will always hate boots because I have huge feet and skinny ankles.

    I actually don’t care if I’m not super-on-trend for weekends. I like classic, preppy clothes like button-downs. I like shapes that work with my body type (swimmer shoulders, short waisted, long legs) over those which are super-trendy.

    I actually laugh at a lot of stuff that’s super-trendy and cringe often when I walk into department stores. I will gladly spend more on weekend and workwear that I feel will survive trends. Does that make me a frump? Perhaps. Do I generally look presentable and pulled together. Yes. Am I required to spend a ton each season to keep up? Nope–accessories and a few tops usually keep me trendy enough.

    • I think there’s a huge difference between being “frumpy” and being “less trendy” – or as I prefer to call it, classic. Frumpy is when your clothes don’t fit you properly and make you look dated. Less trendy is wearing clothes that look good on you and don’t scream “dated” but just aren’t the latest styles – I’d put a button down with tailored jeans in that category.

  8. Fashionable weekend wear is just low down on the list of things I would spend clothes/fashion money on – below nicer work wear, more slinky dresses, hair, make-up, super-cute shoes, nicer running garb…. Heck, I would probably even splurge on a really nice set of PJs before buying trendy weekend wear.

    As long as I look nice (as in, I would be able to walk into a reasonably upscale restaurant and not feel completely ashamed), I feel like I’ve done my weekend-wear job. A few pairs of khakis, a couple cute dresses, a few linen shorts, a couple of flattering tops… done.

    • This. Since about a year ago, I have decided that my weekend wear should be such that I’d feel confident going to a restaurant last minute. Best decision ever!

  9. My work dress code is business casual, with jeans on Fridays, so most of my wardrobe can be worn for both work and weekends. I don’t wear shorts to work or pencil skirts on weekends, but mostly everything else is for any time, not specifically “weekend” or “work” (although some things may be casual Friday work and weekends only). I agree that my silhouettes tend to be the same for work and weekend – slim pants and jeans, no trousers or bootcuts; drapey tops, moved away from fitted cuts; more booties than tall boots.

    I tend to shop mostly in Tier 2, with the occasional 1 and 3. Although I have to say that LOFT has been getting a lot of my business over the past couple of seasons. If I’m wearing a Tier 3 item on the weekend, it’s to go out somewhere nice (which happens every once in a while), not going to a kid’s sporting event or grocery shopping or hanging around the house with the dogs.

    I agree with MJ – a couple of updated items per season are enough – mix them in with your things from past seasons, use current styling from blogs (cuffed jeans, layered necklaces, etc.) if you care about such things, and you’re good.

  10. Anonymous :

    “Once you get used to doing the half-tuck with your jeans on the weekend,”

    Wait, people actually do the half-tuck in real life? There is one woman at my office who does it and it looks ridiculously staged and fake, sort of like her personality.

    • Keilexandra :

      I half-tuck sweaters and tees all the time, with the front half fully tucked and the back hanging out (and a bit of a drapey transition on the sides). I can’t pull off the one-shirt-tail-tucked look, but more power to those who can.

      • I do exactly the same and I feel it helps make my silhouette look more polished.
        The second look you described is something I always thought was a fashion blogger thing

      • Anonymous :

        Oh yeah, to be clear, I’m talking about the J. Crew half-tuck, which is one side of the front tucked in and the other side out. In person, the tucked in half looks too stiff because it’s so hard to get that perfect blousing you see in the catalog without it falling out the next minute. It ends up looking like a sideways mullet.

  11. While we are at it – Does anyone have any experience with Miu Miu or Prada cashmere? They actually fit me (not baggy), and the hues are lovely. I would love to upgrade my weekend sweater game.

  12. Anonymousaur :

    Does anyone else feel like these categories are a bit wonky? Eg. Alice and Olivia can be around $300 just for a blouse… should be in Tier 3. Same with Rebecca Taylor. Both run in the same price range as DVF, Theory, etc. And there is no way that Bebe should be in the same category as either of those…

    IMO something along these lines (I removed some I wasn’t as familiar with to avoid mis-placing them):

    Tier 1A
    American Eagle
    Forever 21
    The Limited
    Old Navy

    Tier 1B
    American Apparel
    Arden B
    Kenneth Cole Reaction
    Lucky Brand
    Matty M
    Urban Outfitters

    Tier 2A
    Ann Taylor
    AX Armani Exchange
    Banana Republic
    BB Dakota
    C&C California
    Ella Moss
    Free People

    Rachel Rachel Roy
    Velvet by Graham & Spencer
    Vince Camuto
    White House | Black Market

    Tier 2B
    BCBG MaxAzria
    Club Monaco
    Eileen Fisher
    French Connection
    James Perse
    J. Crew
    Kenneth Cole New York (not “Reaction”)
    Laundry by Shelli Segal
    Michael Michael Kors
    Patterson J Kincaid
    Rebecca Minkoff
    Rory Beca
    Trina Turk
    Twelfth Street Cynthia Vincent

    Tier 3
    Barneys Co-Op
    Bergdorf Goodman 5F (5th Floor)
    Scoop NYC
    3.1 Philip Lim
    10 Crosby Derek Lam
    Alexander Wang
    All Saints
    Alice + Olivia
    Clover Canyon
    Diane von Furstenberg
    Elizabeth and James
    Haute Hippie
    Helmut Lang
    Kate Spade New York
    Lafayette 148
    L.K. Bennett
    Marc by Marc Jacobs
    Nanette Lepore
    Rachel Zoe
    Rag & Bone
    Rebecca Taylor
    Steven Alan
    Ted Baker London
    Thakoon Addition
    Theyskens Theory
    Tory Burch
    Zadig & Voltaire

    Tier 4 (generally way out of my price range so maybe someone else can take this category and run with it)
    Bergdorf Goodman
    Neiman Marcus
    Saks 5th Ave
    Alexander McQueen
    Barbara Bui
    Derek Lam
    Isabel Marant
    MM6 Maison Margiela
    Proenza Schouler
    The Row

    • I’d put Uniqlo in 1B – maybe it’s cheaper in the UK than in the US but even though it’s cheaper than, say, Asos, it’s a lot better quality.
      Quality-wise it’s comparable to Gap, I would say. Easily.

      • Anonymousaur :

        Eh I don’t shop there all that much so maybe I don’t have enough info to form a solid opinion. One of the (few) shirts I bought from there was a button up the lost two buttons by the third wear. Another top shrank the first time I washed it (and not a little either – so much so I had to give it away as I literally couldn’t get it on anymore). However both incidents were a couple years ago so maybe it has improved since then. Those kind-of turned me off from the brand to the point where I haven’t been back since.

    • Anonymousaur :

      I should also note that I work in a pretty casual (but trendy) industry so what qualifies as “weekend wear” on here is pretty much what I live in all week.

  13. Regardless of what’s trendy, you should always dress for your body type.

    ok, question, and Kat, maybe a topic? Do you have tiers for jeans? I think I am finally ready to splurge on a nice pair of jeans but I have some dilemmas. I know skinny is “in” (and I do wear skinny jeans occasionally, with tall boots, is that really out of style now???) but I really feel like bootcut works better for my body type and I think I would get more use out of them. All of my current jeans fall into category 1 right now. Also, what color wash? I’m thinking darker since it typically looks nicer.

    Also, no one seems to be mentioning shorts. In Texas, there comes a point in the summer when you just can’t do pants anymore and maybe you don’t want to wear a dress to everything. I’ve been liking the skinny bermuda shorts but its a fine balance to make that not look frumpy.